chicago travel itinerary

The Perfect 3 Days in Chicago Itinerary (2024 Edition)

• Last Updated: February 4, 2024

If you’re planning a long weekend trip to the Windy City and aren’t quite sure what to do, keep reading for our epic 3 days in Chicago itinerary!

While Chicago is the 3rd-largest city in the US, it’s often overlooked by travellers who jet for one of the coasts.

In my opinion, Chicago is the best city in the country. New York and LA are great and all, but I’ll gladly take the friendly Midwestern vibe of Chicago instead.

Situated on Lake Michigan, the Chicago skyline is one of the most beautiful in the world. After all, it was here that the first skyscraper was built in 1885!

There’s so much going on here that you could spend a lifetime there and never run out of things to do.

With a solid Chicago itinerary, you can definitely check out the best of the city in 3 days. Let’s get to it!

Table of Contents

When to Visit Chicago

Chicago citypass, getting around chicago, loop walking tour, chicago hot dog, millennium park, art institute of chicago, willis tower, dinner and drinks, museum campus, riverwalk or river cruise, magnificent mile, chicago deep dish pizza, choose your own adventure, museum of your choice, 360 chicago, lincoln park, best hostel in chicago – hi chicago, best mid-range hotel – congress plaza, best luxury hotel – peninsula, brunch/lunch, how to spend a perfect 3 days in chicago itinerary.

Our 3 days in Chicago itinerary includes:

• Shedd Aquarium
• Skydeck Chicago
• Field Museum
• Adler Planetarium
• 360 CHICAGO Observation Deck
• Navy PierMuseum of Science and Industry
• Ferris Wheel
• Crown Fountain

Looking for more awesome things to add to your Chicago itinerary? Be sure to read our guide to the best things to do in Chicago !

Travel Tips for Visiting Chicago

The first step in figuring out what to do during your 3 day Chicago itinerary is planning when you’ll visit.

Winter in Chicago can be painfully cold, which can definitely put a damper on your trip. Unless you enjoy frigid temperatures and cold, biting wind, I recommend skipping out on December-March.

Your best bet is to visit Chicago between May and October. It gets hot and crowded in the summer, but there’s so much going on that it’s worth dealing with those minor inconveniences.

Read Next: Don’t miss out on the best Chicago day trips !

Another huge tip I have before you visit Chicago is to purchase a Chicago CityPASS .

Essentially this is just a multi-use ticket that actually saves you a bunch of money (50% to be precise!) on many great Chicago attractions.

You buy the pass for USD$109, and it includes access to the following:

• Skydeck Chicago and
• Adler Planetarium or the Art Institute of Chicago
• 360 CHICAGO Observation Deck or the Museum of Science and Industry

Best of all, those entrances are mostly express or premium tickets included with the CityPASS , meaning it not only saves you money but saves you time as well.

We highly recommend you pick one up when using our Chicago itinerary to make the most of your time in the city.

Thankfully, getting around Chicago is a breeze thanks to the CTA network of train and bus lines. Chicagoans refer to the train as the “L” because it’s mostly on “el-evated tracks.”

If you’re spending 3 days in Chicago, your best bet is to just pick up an unlimited CTA pass. These cost $20 and are added to a Ventra card.

You can pick up a Ventra card at vending machines for $5 and it’s credited back to your account after you register the card. Read all about getting around Chicago on the CTA website .

You can count on the CTA getting you as far south as the Museum of Science and Industry all the way north to Lincoln Park.

Or consider jumping on and off the open-top bus that will take you all over the city!

In the city center, lots of Chicago attractions are all within walking distance as well.

Now that some of the logistics are taken care of, let’s get this show on the road for your 3 day Chicago itinerary!

Day 1 – Morning

For day 1 of your Chicago itinerary , you’ll need to hit the ground running if you want to maximize your time.

Get a nice early start, crush a substantial breakfast and some coffee, and get ready to rock.

The best way to kick-off your Chicago itinerary is by taking a walking tour of the Loop. This area of downtown is where you’ll find a majority of the sights in Chitown.

You have several options for exploring the Loop. If you enjoy meeting people and getting the insight of a local guide, you can sign up for one of the many options with Free Tours by Foot .

If it’s your first time in Chicago I suggest joining their 10 AM tour of the Loop and Millennium Park. Or if you’re really into architecture, check out their 10:30 Birth of the Skyscraper tour. Both are excellent options!

Those who prefer a DIY approach can check out the many self-guided tours of Chicago from MetroWalkz. This Architecture/Loop tour makes for a fantastic introduction to the city and is pretty easy to follow.

Whichever option you choose, you’ll get to see some of the most iconic places in the city in just a few short hours. A few of the highlights include the historic start of Route 66, the great Chicago Theatre.

READ NEXT: While you’re exploring the Midwest, be sure to check out the best things to do in Minneapolis, Minnesota !

Day 1 – Afternoon

At this point, the order in which you do things depends on which type of tour you chose. You can be flexible, as it’s a short walk between the next couple of destinations.

Before we move along with the 3 day Chicago itinerary, it’s time for lunch! If you’re down in the Loop and you want to try a local favourite, the choice is easy…

There are countless restaurants to choose from in the Loop, but you don’t want to travel all the way to Chicago to get stuck eating at some overrated chain or overpriced tourist trap.

Al’s is a classic local joint serving up the famous Chicago style hot dogs and their specialty Italian beef sandwiches.

One thing to know, a Chicago dog is an all-beef dog on a sesame seed bun. It comes topped with tomato, chopped onions, pickled peppers, relish, a pickle spear, and yellow mustard. Quite simply put, it’s heaven on a bun.

I would be remiss if I didn’t also mention Portillo’s. They also make one of the best Chicago style hot dogs out there.

While they’re a bit out of the way for today’s itinerary, keep them in mind if you’re craving another hot dog during your 3 days in Chicago (and trust me, you will).

Read More: Spending time exploring the Midwest? Be sure to check out our post on all of the best things to do in Kansas City !

Even if you visited on your walking tour, it’s worth it to double back to Millennium Park for further exploration.

There’s a lot of cool stuff to see here, including the Crown Fountain and the Cloud Gate.

The latter is commonly referred to as “The Bean” and is one of Chicago’s most popular places to take photos in the city. Don’t forget to snap that quintessential Chicago shot for the ‘gram and keep on moving.

Other Chicago attractions you must see in Millennium Park include the Jay Pritzker Pavilion, the BP Pedestrian Bridge, the Chicago Cultural Center, and the Lurie Garden.

You can easily spend a couple of hours in Millennium Park, especially on a nice day.

Buckingham Fountain and Grant Park are within this same area as well if you want to keep exploring on foot.

While there’s plenty of amazing public art in the Loop, you can’t top the collection at the Art Institute of Chicago. Art lovers will definitely want to include this on their 3 day Chicago itinerary.

Tucked away on Michigan Avenue on the south end of Millennium Park, the Art Institute of Chicago has a seriously impressive collection here and there are always new exhibits featuring modern and contemporary art.

Make the most of your Chicago CityPASS to gain fast entry into the Art Institute of Chicago.

The museum is open daily from 10:30 AM to 5 PM and stays open until 8 on Thursdays.

Day 1 – Evening

Before the day turns into night, it’s time to hustle over to your next destination of your 3 day Chicago itinerary. Try to time it just right so you make it there about an hour before sunset. Trust me, it’s worth it!

Whether or not you hit the museum, your next stop should be the Willis Tower. This is one of Chicago’s most iconic skyscraper in the city that invented them!

Formerly known as the Sears Tower, this was the tallest building in the world for 25 years. It stands at 442 meters (1,450 feet) tall and is currently the 2nd-tallest building in the US.

If you plan to visit Chicago in 3 days, you definitely need to check the Willis Tower off your to-do list.

Head to the 103rd floor to access the Skydeck Chicago and step out onto “The Ledge” – a glass balcony that lets you look straight down. You’ll want to see views of the city from this spectacular perspective!

Don’t forget, the best time to go to the Willis Tower is just before sunset. It stays open until 10 PM from March through September and tickets cost $25 for adults and $17 for children.

Once again though, no need to pay extra for a ticket, because the entrance to the Skydeck Chicago is included with your CityPASS .

To celebrate making it through a massive day 1 of the Chicago itinerary, it’s time for dinner and drinks! When it comes to wining and dining, the world really is your oyster in the Loop.

After such a big day, you may want to call it a (somewhat) early night. We’ve still got a lot of ground to cover with this 3 days in Chicago itinerary! Of course, if you want to go out and rage, go for it!

Day 2 – Morning

If you don’t have breakfast included at your hotel, I highly advise you to start day two off at Yolk’s South Loop location.

This is the perfect spot to load up with a big breakfast and coffee before another big day in the city. Go ahead and carb up – there’s going to be a lot of walking today!

After breakfast, walk across the street to check out Agora – a sculpture composed of 106 headless figures.

Keep walking east towards Lake Michigan to reach the Museum Campus. Here you’ll find the Field Museum, Shedd Aquarium, and the Adler Planetarium.

With just 3 days in Chicago, you’ll probably want to just visit one. Having been to all three, I’ll cast my vote for the Field Museum.

There are so many cool exhibits at the Field Museum and they’re always changing.

At the moment, they have: Inside Ancient Egypt, Bird’s of America, and Brewing Up Chicago, among others. Check their website to see what’s going on before you visit.

Tickets for the Field Museum cost $26 for adults and $19 for children for basic admission.

If you got the CityPASS, your admission is included in all three, unless you hit the Art Institute on day one. If you’ve got the pass, you might as well hit the aquarium as well.

To be honest, the aquarium is pretty sweet. Even if you don’t have the CityPASS, you should probably try to squeeze it in.

Tickets are $40 for adults and $30 for kids and you’ll definitely get your money’s worth.

Day 2 – Afternoon

There are a few cafes and food stands around the museum campus, so go ahead and grab a snack and a drink before powering on.

This is one of those days where it’s best to have a big breakfast and dinner and just graze during the day. When you’re trying to cross off so many things to do in Chicago in 3 days, you gotta keep moving!

The museum campus is the southern part of Grant Park. Known as “Chicago’s Front Yard,” this massive green space is to Chicago what Central Park is to NYC.

Take a stroll through the park to see such landmarks as the Buckingham Fountain, the Rose Garden, and the Seated Lincoln Statue. There are plenty of benches if you need to sit down and chill for a bit.

Grant Park also hosts some of the biggest events in the city, such as the Taste of Chicago and Lollapalooza.

Some are free and others cost hundreds of dollars, so be sure to check the calendar of events to see what’s happening before you book your trip.

Hug the coast and keep walking north along the Lake Michigan until you reach the Riverwalk. This scenic pedestrian path along the Chicago River is the perfect place for a leisurely stroll.

If your feet are feeling a bit tired from all the walking, you can enjoy the spectacular Chicago architecture on this fantastic river cruise instead .

Taking in the sights along the Chicago River is definitely one of the top things to do in a 3 day Chicago itinerary.

Wendella Boats has an architecture river cruise that comes highly recommended. Make sure you have your camera for this one, as you’ll get some epic views of the city.

Day 2 – Evening

I’m sure you’re ready to eat your hand by now, but you’ve just got to soldier on for a bit longer. Trust me, it’s going to be worth the wait!

On the other side of the Chicago River, you’ll find the Magnificent Mile, a short stretch of Michigan Avenue in downtown Chicago. This is the city’s premier commercial district, full of high-end shops, nice restaurants, and boutique hotels.

Along the Magnificent Mile, you’ll also see several historic skyscrapers, such as the Wrigley Building, Tribune Tower, and the Old Watertower.

The latter is home to the City Gallery, which has Chicago-focused photography exhibits. It’s totally free to visit, so you may as well check out while you’re in the area.

Even if you’re not doing any shopping, it’s worth a quick stroll along the famous Michigan Avenue. That’s because it’s leading you to…

You had the hot dog on day one, so it’s time to dig into some Chicago-style deep dish pizza.

Since it’s cooked in such a deep pan, a Chicago-style deep dish pizza can be stuffed with mountains of cheese. Of course, you can add whatever other toppings you like as well.

Now you see why I’ve been torturing you by making you walk around all day waiting for dinner! This deep dish pizza is seriously delicious and filling, so I wanted to make sure you could at least have a few slices.

There are plenty of places cooking up Chicago-style deep dish pizza, but I brought you here because two of the best are easily accessible.

Get to the corner of Michigan and Superior and you have an important choice to make. Take a left and you’ll go to Giordano’s. Hook a right and you’ll be at Gino’s East.

Just go ahead and flip a coin because you win either way. Both places are legendary for their deep dish pizzas, so you really can’t go wrong.

Not far from the Magnificent Mile, you’ll find Navy Pier. If you’re spending 3 days in Chicago on a long weekend, this is the perfect place to be on a Saturday night.

First up, you can take a ride on the Centennial Ferris Wheel. Tickets cost $18 for adults and $16 for children, but you can save a few bucks if you book online .

From the end of May until the end of August, Navy Pier also hosts bi-weekly fireworks shows. These happen on Wednesdays at 9:30 PM and Saturdays at 10:15.

To take in the spectacle, you can find a spot to stand on the Navy Pier or sign up for an evening cruise. Enjoying the fireworks as you cruise around is a great addition to your Chicago itinerary.

If you have any gas left in the tank after all of the activities at the Navy Pier, congratulations! I just ran you ragged all over Chicago on day two. That’s why it’s time to choose your own adventure!

For many, that will probably involve grabbing a casual drink from the hotel bar and getting some sleep. That’s totally fine. I’m getting to the age where that sounds like a perfect Saturday night!

For the young whipper-snappers among us, you’re probably itching to enjoy a big night out on the town. Go for it, you crazy kids!

Your options are endless. There’s live music of all varieties, comedy clubs, and just about every type of bar under the sun.

Whether you’re looking for a speakeasy that whips up creative cocktails, a classy wine & jazz joint, or just a good ole’ fashioned dive, you can find it in Chicago.

In this part of the city, one of my personal favourites is Three Dots & a Dash. This awesome tiki bar has an impressive selection of cocktails that will transport you to the Caribbean in no time.

If you’re going to go hard one night, this is the one to do it! Bars in Chicago typically close at 2 AM, but there are several that stay open as late as 4 on the weekend. You’ve been warned…

Day 3 – Morning

How early the last day of your 3 day Chicago itinerary starts depends entirely on how late your night went!

Those who already regret ordering that last round may need to sleep in a bit and smash a greasy brunch, while the go-getter set who actually slept will be up and at them. Life is all about choices, people!

Whatever you did the night before, get some food and caffeine in your system and get out there to wind down this 3 day Chicago itinerary.

Our third and final day in Chicago starts off with a leisurely museum visit. Within a few blocks of each other, you can take your pick between three excellent museums.

Art enthusiasts will gravitate towards the Museum of Contemporary Art, which highlights post-WWII art.

Those more interested in architecture and antiques may want to hit the Richard H. Driehaus Museum. It’s in a restored 19th-century mansion and brings you right back to the Gilded Age.

Chicago is very much a sports city, as people here are very passionate about their teams. Check out the Chicago Sports Museum, which is full of memorabilia and plenty of fun exhibits.

I know I already sent you to the Willis Tower on day one, but it’s still worth a trip to John Hancock’s 360 Chicago on Michigan Avenue.

This observation deck on the 94th floor of the John Hancock Building provides a whole different perspective on the city that you will definitely want to see.

Plus, if you bought a CityPASS your admission to the John Hancock building is already included! If you didn’t grab the pass, a ticket is $25 for adults or $15 for children.

Those who are feeling adventurous (and not hungover) may want to take a ride on Tilt – Chicago’s highest thrill ride.

If you need some hair of the dog instead, you can grab a ticket that includes your choice of adult beverage. Sunday Funday!

If you don’t purchase the Chicago CityPASS consider purchasing this ticket to enjoy the views from the 94th floor of the John Hancock building’s 360 Chicago.

Day 3 – Afternoon

Once you come down from 360 Chicago in John Hancock building, you have plenty of options for lunch. Within a few blocks, you can find Cuban, Vietnamese, Mediterranean, and the Chicago staple of deep dish pizza.

If you want a lunch with a view, consider eating at The Kennison. This upscale bar and restaurant offers sweeping views of Lincoln Park. The menu is modern American and they have lots of amazing cocktails and drinks.

Hop on the bus, order an Uber, or walk 30 minutes to our next destination – Lincoln Park.

There’s a lot to do in this huge park on the shores of Lake Michigan. North Avenue Beach is at the south end.

On a beautiful day in Chicago, it’s hard to beat lounging on the beach and swimming in the lake. You can also play some beach volleyball and rent a SUP or bike if you want some more activity.

In the middle is the Lincoln Park Zoo, which is totally free to visit. Sightseeing gets expensive, so this awesome free attraction is definitely one of the top things for any Chicago itinerary.

After such an action-packed 3 days in Chicago, you should definitely just take it easy and enjoy all that Lincoln Park has to offer. You’ve covered some serious ground in a short time, so congrats on that!

Day 3 – Evening

At this point in the journey, you have absolutely crushed 3 perfect days in Chicago. Order a celebratory drink or two and enjoy your last evening in the city!

What you choose to do with your final night all depends on when you’re visiting and what your interests are. That’s why it’s time once again to…

In a perfect world, the Cubs would be playing a night game while you are visiting Chicago. You could head north to Wrigley Field and enjoy America’s pastime at the 2nd-oldest ballpark in the country.

The Cubs play about 80 home games between April and September, so there’s a good chance they’ll be in town when you are. Even if you’re not a baseball fan, I recommend hitting a game if at all possible.

Chicago actually has two MLB teams. But the White Sox ballpark is way south of where you’ll be on day three and not worth the trip if you ask me.

If you’re making a trip to Chicago between October and April, you may be able to catch the Bulls (NBA), Blackhawks (NHL), or the Bears play a home game. Check their schedules to see what’s going on when you’re in town.

Those who prefer a good laugh can head back to the south end of Lincoln Park. Just a block away, you’ll find three of the city’s best comedy clubs – Second City, UP, and Zanies.

I pretty much always travel to Chicago for live music, so you know I’m going to toss that in here!

The city has an epic music scene and there’s always something playing here. Whether you’re into rock, hip-hop, jazz, electronic, blues, pop, or whatever it is you wacky Millenials listen to these days, there’s a show for you.

I usually check Jambase to see what shows are playing.

Congratulations, my friend. You made it through an insane 3 days in Chicago itinerary and experienced the best that the Windy City has to offer.

I’d say that calls for a toast! If you want to finish up with a true Chicago experience, order a shot of malort. This infamous Chicago liquor is pretty hard to describe, so I’ll let its label do the work:

“ Malort has the aroma and full-bodied flavor of an unusual botanical. Its bitter taste is savored by two-fisted drinkers .”

I’m not going to sugar coat it – this stuff is awful. It’s a rite of passage here in Chicago, though. Eat the hot dog. Drink the malort. Praise be to Ditka. You’re now a little bit Chicagoan.

After you finish that putrid shot of malort, switch to a delicious Chicago craft beer. There are plenty of choices here, including Lagunitas, Revolution, and Goose Island.

I hope you enjoyed this massive tour of Chicago!

From Navy Pier, to Millennium Park, the Chicago riverwalk, the famous Chicago hot dogs and more, visiting Chicago is never dull.

Hopefully this 3 day Chicago itinerary has been inspiring and gives you an idea of what to do in the Windy City.

Chicago Itinerary Travel Guide

Now that you know what to do with a long weekend in Chicago, I’ve gone ahead and put together a mini-guide to this awesome city to help you decide where to stay, where to eat, and of course where to drink!

Where to Stay in Chicago

You’re probably wondering where to stay, especially if it is your first time in Chicago.

Most first-time visitors choose to base themselves in downtown Chicago, and for good reason. Here are countless options for accommodation, sightseeing, dining, and nightlife.

As you might expect, staying downtown comes with a price tag. Other popular places to stay that are a bit cheaper include River North, Lincoln Park, Bucktown, and Wicker Park.

When it comes to places to lay your head, Chicago has it all. The city has 5-star luxury hotels, quaint B&Bs, dingy motels, fun hostels, and plenty of options on sites like Airbnb.

Here are a few options to suit all budgets:

Hostelling International is a trusted name in backpacker accommodation, and their downtown Chicago location is definitely the best hostel for visiting Chicago.

They have several different options for both private and dorm rooms. You can get a bunk for under $40 a night here – a steal for this fantastic location.This includes a free breakfast, and they also have free walking tours during the day and free activities at night.

That’s not all, though. They’ve also got a huge lounge with a ping pong table and a TV room with plenty of movies. Best of all, this hostel is environmentally-friendly. They have reusable products in the kitchen and recycling points all around the building.

This historic downtown Chicago hotel dates all the way back to 1893. Don’t worry – it’s had several updates over the years!

You really can’t beat the location of this place. I usually stay with friends in more residential neighbourhoods, but this is my go-to spot when I want to be in the middle of all the action.

From here, you’re just across the street from Grant Park. Many of the rooms here even boast a nice view of Lake Michigan. With rooms starting as low as $115 a night, it’s a pretty awesome deal staying here.

The 5-star Peninsula Chicago was recently named the 2nd best hotel in the country by US News & World Report. This place is fancy, people!

It’s located right on the Magnificent Mile, so it’s surrounded by high-end shops. This is definitely where the fabulous people stay.

In addition to the super swanky rooms, you can enjoy the hotel’s three different restaurants and its impressive fitness centre.

Taking up the top two floors of the building, it features a 25-meter pool and an award-winning spa. Rooms start at around $600 a night here.

Where to Eat and Drink in Chicago

I’m very fortunate to have a good friend who is heavily involved in the hospitality scene in Chicago.

I reached out to him to get a list to add to this guide. He’s never done me wrong with food & drink recommendations, so you can take these to the bank the next time you visit Chicago!

• Dove’s Luncheonette
• Joe’s Stone Crab: It’s a steakhouse and it’s hard to get into at night, but if you go for boozy brunch it’s great.
• Parson’s Chicken & Fish: Not really brunch but just a great people-watching patio.
• Big Star: Chicago classic taco joint with highly sought after patio
• 3 Arts Club

• Bavette’s Bar & Boeuf
• The Roister
• Green Street Smoked Meats: A great BBQ joint and High Five Ramen is below.
• Maple & Ash
• Nico Osteri
• Billy Sunday
• Aviary (try to get down to the office)
• Violet Hour
• Start at Scofflaw and work your way over to Best Intentions
• Longman & Eagle 
• The California Clipper: Been around since before prohibition!

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Sasha and Rachel

Hi, We’re Alesha and Jarryd!

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Home » North America » Chicago

CHICAGO Itinerary • MUST READ! (2024)

With incredible works of public art scattered all around the city and free access to many of its museums and art centers, Chicago is a cultural hub! It’s also America’s third-largest city and the birthplace of the modern skyscraper.

This immense and beautiful city has a vibrant outdoor culture, with many activities and attractions to enjoy. You’ll find unique and delicious cuisine, fantastic outdoor fun, and great local sports. We’ve put together an itinerary for Chicago which covers all the best attractions in the city!

Pack your walking shoes and prepare to visit some iconic places. With one of the most recognizable skylines in the world and a community welcoming to travelers, you’ll have the time of your life!

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Best Time To Visit Chicago

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Chicago is known as the windy city! However, many days outside of winter are balmy and perfect. All seasons are distinctly represented in Chicago. The city has hot, frequently humid summers, and wet, cool springs. Fall can be pleasantly temperate fall with a cold winter to follow. When you choose to go depends on your seasonal preferences!

Wondering when to visit Chicago? Most tourists plan their vacation in Chicago during the summer when it’s hot. However, we suggest going in early autumn or late spring, when the crowds are much calmer and the weather is mild.

Unfortunately, many of Chicago’s outdoor attractions close for the frigid winter season (November – March), so keep that in mind if you are wanting to visit during this period. It is a great time to visit if you’re coming to Chicago for its many indoor activities and don’t mind the cold!

With a Chicago City Pass , you can experience the best of Chicago at the CHEAPEST prices. Discounts, attractions, tickets, and even public transport are all standards in any good city pass – be sure invest now and save them $$$ when you arrive!

Chicago is one of the largest cities in America, with sprawling neighborhoods and lots to do in all of them. Accommodation ranges from top luxury on the Magnificent Mile to low-budget hostels in Chinatown. You can find a place for any budget and a range of interests!

The best place to stay in Chicago is undoubtedly Downtown Chicago/The Loop. It’s central and home to Chicago’s most prolific and most important landmarks, you will hardly need to leave the area and will save time and costs on public transportation! It’s an especially good idea if you’re only spending two days in Chicago.

The Loop is designed in a grid pattern, making it very navigable to first-timers. No matter where you stay in the neighborhood, you’ll find great restaurants and things to see no more than a block away.

If you’re interested in staying somewhere a little more obscure and experiencing a different side of Chicago, find a place in West Loop! It’s a great neighborhood for foodies, and there are many galleries and cafés nestled away, far from the Chicago skyscrapers (but not too far).  

There are hotels, hostels, hovels and Airbnbs in Chicago so suit every budget. In fact, if you are really on a budget, you can find some cheap and comfy motels in Chicago .

If you’re looking for something that better suits you, you can also have a look at our more detailed guide on where to stay in Chicago !

Best Hostel in Chicago – Hi Chicago

This beautiful, expansive hostel is located in the heart of Downtown Chicago. It’s a great place to meet fellow travelers. It includes a pool table, bar, ping-pong table, and other great general areas.

Rooms are clean, comfortable, and gender-separated. Best of all, you get a large breakfast, a spacious locker, and guided tours of the city, all free!

To see more hostel options, check out our top picks for hostels in Chicago .

Best Airbnb in Chicago – Modern loft for 2

With this basic, convenient and well-priced studio apartment, you have access to a comfortable, queen size bed, full kitchen, on-site laundry facility, free wifi, and an awesome host who will recommend you places to visit, attractions to see in Chicago.

Best Budget Hotel in Chicago – Best Western Grant Park Hotel

A short walk from some of Chicago’s top attractions, this budget hotel is comfortable and fun. The rooms are clean, and the staff are helpful and knowledgeable. There’s an on-site restaurant, fitness center, and business center.

The beds are large, and if you book a room on one of the top floors, you’ll enjoy fantastic views over Chicago!

Chicago is not a very walkable city, as it is very large. However, walking within the neighborhoods is very doable. Most of the attractions and landmarks are centered in Downtown Chicago, so we suggest you go by foot here. Walking is also a great option because it allows you to see more of the people and culture of the city!

There are also fantastic public transport systems in Chicago. You can catch the L Train, which stops all over Chicago. It’s cheap and easy to use, navigable to first-timers and tourists.

Alternatively, you can take the bus. These stop right outside of most Chicago points of interest, making it ideal. However, it can be difficult for newcomers to navigate, and you may struggle to catch a bus that’s actually going right where you need to be!

Another great way to explore a few of Chicago’s neighborhoods is by bicycle. The city even has a Divvy bike-share system, which allows you to grab a bike from one of the hundreds of stations in the city. You can get a day-pass for these or a single fare.

The Art Institute of Chicago | Garfield Park Conservatory | Millennium Park | The Field Museum | Willis Tower Skydeck | Annoyance Theatre & Bar

On the first day of your Chicago Itinerary you’ll explore some of the city’s most iconic landmarks and beautiful places. Wear walking shoes – everything is within walking distance!

Day 1 / Stop 1 – The Art Institute of Chicago

• Why it’s awesome: It’s one of the world’s greatest art museums.
• Cost: $25; $35 for fast pass with audio guide .
• Food Recommendation: Grab breakfast at the Corner Bakery Café.

Beautifully set out, the Art Institute is a fantastic experience and a great start to your Chicago Itinerary. Its displays are always rotating and being added to, so if you’ve been here years ago, don’t let that stop you from going again.

Admire the diverse range of art on display, broaching topics from South African Apartheid and resistance to Japanese life, to modern ideas of femininity and beauty. Attend talks on art and history in the museum! Get the audio guide and learn about the art and exhibitions as you go at your own pace.

You can spend the whole day here, but we suggest you spend 2-3 hours in the art museum. You can get a floorplan of the museum at the entrance, to help you plan your route and ensure you see everything you want to see.

Whether you love art or history or neither, this is a Chicago experience you don’t want to miss! You are permitted to take photographs, which is great, because you will really want to.

Day 1 / Stop 2 – Garfield Park Conservatory

• Why it’s awesome: A green oasis under glass, it’s really something special.
• Cost: Free, with an optional donation.
• Food Recommendation: Find something delicious at the charitable restaurant Inspiration Kitchen.

Explore the Conservatory’s 2-acres of lush indoor display houses and exotic outdoor gardens! A beautiful getaway from the concrete jungle, the gardens host an incredible amount of flora from all over the world.

Visit the desert house for cacti and succulents, or the Palm House and Fern room, which evokes a swampy prehistoric landscape you can get lost in. In Sugar From the Sun, you’ll find botanic environments themes around water, air, sunlight, and sugar. Here you can learn about how plants make energy!

The outdoor gardens are a fantastic place to stop and enjoy a picnic, or a bit of lazing on the grass and soaking up the sun. These gardens have more to offer than grass though! The Monet Garden and Sensory Garden are wonderlands for the senses.

You can get a digital guide to the Garfield Park Conservatory for free on your phone, or just stroll around and enjoy the gorgeous plantlife. It is certainly one of the most beautiful places on our Chicago itinerary.

Day 1 / Stop 3 – Millennium Park & Cloud Gate

• Why it’s awesome: The cultural and artistic hub of Chicago, the park is a must-see.
• Cost: Free!
• Food Recommendation: Pancake stacks at Wildberry Pancakes & Cafe.

If you’re planning a trip to Chicago, you have to visit Millenium Park. A unique town square, it’s leafy landscape is only a backdrop to state-of-the-art architecture, art and landscape design. Home to much of Chicago’s cultural offerings, you’re bound to find something amazing to do here. Family events, concerts, exhibitions, and tours are all  offered!

The Park’s unique, immense outdoor concert venue was designed by renowned architect Frank Gehry and spans much of the park. This is where you’ll find much of the activity!

There is also, of course, Cloud Gate. Featured in many movies and pop culture references since its creation, Cloud Gate is the most recognizable Chicago landmark. The seamless sculpture reflects the Chicago skyline. And when you walk beneath it, it reflects you as well from myriad angles. Shaped similarly to a bean, it’s affectionately referred to by locals as ‘the bean’.

With so many artistic attractions, Millenium Park is a must-see even if you’re only spending two days in Chicago! It will charm you no matter what!

Day 1 / Stop 4 – The Field Museum

• Why it’s awesome: The exhibitions are fascinating, and there’s so much to discover.
• Cost: $24 – $38 ( Get an online ticket for fast access!)
• Food Recommendation: Get Chicago streetfood classics at Kim and Carlo’s Hotdog Cart.

A brilliant museum for the natural sciences, Field provides an opportunity to learn and explore everything related to science and natural history! Discover dinosaurs, ancient artifacts, and groundbreaking scientific discoveries.

Research is always continuing at the museum’s extensive labs, leading global initiatives to discover more about our world. Spend a few hours exploring collections around different cultures from the past and present, fossils and meteorites that tell us about the earth’s history, and weird and wonderful animals!

Everything is consistently updated and well-maintained, with amazing attention to detail. The T-Rex skeleton is the most complete one ever found! It’s quite a thing to behold.

Insider Tip: Even if you spent the whole day here you wouldn’t be able to see everything. So, decide what you really want to see at the outset, and give yourself three hours to take in all you can!

Day 1 / Stop 5 – Willis Tower Skydeck

• Why it’s awesome: The best view over Chicago.
• Food Recommendation: Try Chicago’s deep-dish pizza at Giordano’s, in Willis Tower.

With a glass-bottomed deck and impeccable views, there’s no better location to watch the sunset. This is a great place to take photos of Chicago, and of course, yourself with it. In fact, your ticket includes three professionally taken photographs!

The staff is very nice and helpful, elevating the experience. There is always a line, but it moves quickly. A typical skyscraper experience, the Willis Tower is worthwhile for unparalleled views. You will be able to see most of the other stops on your Chicago itinerary!

Day 1 / Stop 6 – Comedy at Annoyance Theatre & Bar

• Why it’s awesome: Get a good laugh with Chicago locals.
• Cost: $5 – $12
• Food Recommendation:  Enjoy bar snacks or go to the nearby Ann Sather Restaurant.

A great way to spend the evening, Annoyance Theatre and Bar offers up a lot of laughs. With different acts every night, improv shows, comedy sketches, and musicals, there’s something for everyone, every night.

The Annoyance has played in comedy theatres all over America and has even been on TV, but their home-base is here in the windy city. Have a look at what’s on during your vacation in Chicago! You may even find a full-length cabaret or comedy musical.

With a fantastic festival-type atmosphere and tasty, well-priced drinks, you can’t go wrong. The performances are fun and creative, with a large cast and intimate setting! So grab a drink and find a seat. It’s a barrel of laughs.

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Grant Park and Buckingham Fountain | Chicago Cultural Center | Museum of Science and Industry | Navy Pier | Wrigley Field | Magnificent Mile | Jazz at Blue Chicago

On day two of your itinerary for Chicago, you’ll see and do even more! Prepare to eat amazing food and enjoy some of Chicago’s best cultural offerings.

Day 2 / Stop 1 – Grant Park and Buckingham Fountain

• Why it’s awesome: One of the biggest parks and fountains in the world!
• Food Recommendation: Get some creative hot dogs at Devil Dawgs on State.

Surrounding the Millenium Park and extending far beyond it is Grant Park. This giant public park is affectionately referred to as ‘Chicago’s front yard’, and the first stop on your Chicago itinerary’s second day. Located in the central business district, you can stroll through and find hundreds of sculptures and public works of art.

Spend the early hours of the morning here while you wait for everything to open. (Chicago starts its days late). It’s a beautiful green space, and you’ll often find yoga sessions and ball games that anyone can join in!

While you’re here you have to seek out the Buckingham Fountain! Designed in 1927, the fountain is one of the largest in the world. It usually runs from 8 am to 11 pm daily, from May to October. Every hour, the Fountain produces an incredible 20-minute display! So if you’re visiting during this period, it is not to be missed.

Day 2 / Stop 2 – Chicago Cultural Center

• Why it’s awesome: Beautiful building with exhibitions and events.
• Food Recommendation: Grab a quick bite at Toni Patisserie & Cafe.

If you’re wondering what to do in Chicago for free, this is one of the best places to be! The architecturally stunning building is host to many wonderful things and none of them cost a thing.

Find an art show, performance piece, musical event, or something else while exploring its Art Deco interiors.

The whole building is covered in beautiful mosaics. With a giant glass dome and ornate staircases, it’s a wonderful place to go even when nothing else is going on. It’s a lovely place to relax and take in some beauty.

Day 2 / Stop 3 – Museum of Science and Industry

• Why it’s awesome: Impressive, interactive exhibits and great fun.
• Food Recommendation: Italian food at Piccolo Mondo.

With interactive exhibits of all kinds, the MSI brings science to life. Descend into a coal mine, float outside the international space station in a virtual reality experience, and feel and the physics of a tornado created by man!

There is so much to do, you will be enveloped in the excitement of where we’ve been and where we’re going as a species and as a planet. There’s even a behind-the-scenes tour so you can explore how such a sprawling, impressive museum and scientific center works.

One great new exhibit is Wired to Wear and is the first exhibit ever dedicated to wearable technology and where it can take us. Part of the future, it’s quite something to see this in the present and one of the best places to visit in Chicago .

Watch a film in the five-story, domed, wraparound movie theatre. The glory and intensity of nature is well-suited to such large-scale viewing. With hands-on experiments, interactive and interesting exhibits, and great, knowledgeable staff, MSI is a definite must-see on your trip to Chicago.

Day 2 / Stop 4 – Navy Pier

• Why it’s awesome: A favorite for locals and tourists, this place is packed with things to do!
• Food Recommendation: Find tasty seafood on the pier at Riva Crab House.

No ordinary pier, the Navy Pier has a wide and eclectic range of activities for solo backpackers in Chicago , families, couples, and friends.

Go for a ride on the iconic Centennial Wheel, with fantastic views over Chicago and Lake Michigan. Explore virtual reality or test your strength on the climbing wall. Navy Pier is also the primary departure point for many lake cruises and bus tours, so its the perfect place to go if you have a little more time than expected!

You’ll find public art and exhibitions, cultural attractions, a great variety of shopping opportunities, and of course, amazing restaurants. With such an eclectic range of activities, it could be the only thing on our Chicago Itinerary!

Day 2 / Stop 5 – Wrigley Field

• Why it’s awesome: Baseball has been played here for over 100 years!
• Cost: $13 – $154 for a game
• Food Recommendation: Get something at the lively sports bar Murphy’s Bleachers.

Wrigley Field is a great American Ball Park with great, enthusiastic fans and a fun environment and vibe. Everything is well run with helpful and friendly security and staff, and well-maintained restrooms.

Across the street from the field, you can find plenty of sport-themed pubs and bars. Go after the game, and celebrate your team’s win or mourn their loss with people who are doing the same. It’s great fun, either way.

With over 100 years of iconic baseball games here, it’s a great place to spend a few hours and feel the spirit of Chicago. Recent renovations to the field add convenience to the ambiance of history, and as per tradition, you can buy hotdogs and beers at in-house vendors before taking your seat.

If you are more interested in the famous field than the game, you can go on a Wrigley Field tour! These last 90 minutes, and allow you to experience the beauty and charm of the historic field and learn about its captivating history.

Day 2 / Stop 6 – Magnificent Mile

• Why it’s awesome: Admire skyscrapers and boutique shops in this world-famous upscale shopping district.
• Food Recommendation: Mediterranean food at The Purple Pig.

Chicago’s premier commercial district, the Magnificent Mile, is where to go to get all your Chicago shopping done! More than this, it’s a great place to explore for its luxurious and posh atmosphere, with high-class fashion outlets, restaurants, and hotels.

We love window shopping in this district and people-watching! There are also numerous Chicago landmarks , including the Chicago Water Tower and the John Hancock Center. In fact, there are over 50 landmark structures here!

Stroll down the long, beautiful avenue and admire so much of what makes Chicago a great international destination, right in one city center. It’s also nicknamed the Million Dollar Mile. Walking down it, you’ll understand why!

At night, everything lights up beautifully. Turn into a few taverns and art galleries for a laid-back and enjoyable cultural bar-hopping experience. Hopefully, you’ll meet a few locals!

Day 2 / Stop 7 – Jazz at Blue Chicago

• Why it’s awesome: Fantastic blues and jazz and a great vibe
• Cost: $10 – $12
• Food Recommendation: Try Peruvian food at Tanta Chicago

Don’t worry if you’re not spending the weekend in Chicago! With live Chicago Blues seven nights a week, this is the perfect end to your two day itinerary in Chicago. This blues bar is the perfect place for it – a traditional ‘hole in the wall’ style establishment with well-priced drinks and an old-school atmosphere.

The world-renowned blues bar has been running since 1985 and is packed with locals and foreigners every night. Be sure to book beforehand or go early, and keep in mind that only adults over 21 may enter.

Chicago Blues is an eclectic style of blues and jazz music which came about with the migration of African Americans from the South to the Midwest. The performances at Blue Chicago reflect this rich, powerful and difficult history, with great energy and a surplus of talent.

An important part of Chicago’s history and culture, this music is a celebration of life. to watch it and participate in continuing a proud musical tradition is really something special, and certainly one of the best things to do when spending a weekend in Chicago .

This beautiful, expansive hostel is located in the heart of Downtown Chicago.

• Free Breakfast

Chicago River Cruise | Chicago Food tour | Richard H. Driehaus Museum | Mob and Crime Bus Tour | Football Game at Soldier Field

If you’re spending three days in Chicago or more, these are the best activities and attractions to include in your Chicago itinerary! They’re a great way to explore the city and learn more about that unique Chicagoan culture.

Chicago River Cruise

• Relax with a drink while cruising along the river.
• Get insight into landmark buildings and marvel at the legendary architecture.
• A 75-minute cruise on a state-of-the-art vessel.

Spend some time exploring one of the biggest Chicago attractions – the gorgeous river. On the architecture tour, you’ll cruise along all three branches of the Chicago River, spotting your favorite landmarks and learning about the city.

From the Navy Pier, you can catch numerous different types of cruises to suit your interests, like a dinner cruise, buffet cruise, or sport-themed cruise. You can also choose between different types of boats!

Our top choice is an architectural river tour, offering a captivating exploration of Chicago’s hidden gems and iconic landmarks. Among others, you’ll see Tribune Tower, the Wrigley Building, Marina City, and Willis Tower.

Relax and enjoy a drink from the bar. The cruise is 75-minutes, just enough time to relax and recover your energy before plunging back into Chicago’s central city hub!

Chicago is known as the birthplace of the skyscraper, and the home of modern American architecture. There is so much to learn and appreciate here. On the tour, you will have an expert guide, with facts, anecdotes, and answers about all of Chicago’s attractions!

Skip the ticket office and proceed directly to boarding by pre-purchasing your ticket online . One of the world’s most beautiful cities and a thriving modern metropolis, Chicago is well worth exploring this way.

If you want a more unique and exciting way to see the river and Lake Michigan, then consider chartering a yacht at an affordable price.

Chicago Food tour

• Join a fun and enthusiastic foodie guide while touring Chicago.
• Sample some of Chicago’s best culinary offerings.
• Get insight into the art, architecture and everyday life of the metropolis.

This foodie Chicago walking tour is a simple classic – stroll through the city learning more about it from a local, while trying all of its best and most exciting foods.

Your guide is knowledgeable and friendly, and will tell you about much more than just the food! The city has so much to see and explore and has such an interesting history, including famous 1920s gangsters like Al Capone. It’s fantastic to explore it with a local, who knows all the best and worst things about the city. You can also get tips on how to explore Chicago’s food and dining scene some more if you’re interested.

Chicago is famous for its American-style food innovations, like the deep-dish style pizza, and Chicago-style hot dogs. You’ll dig into some of these, among other foods! The tour lasts three-hours long, so you have ample time to eat and explore.

You will also get to meet new people on your tour, and enjoy your meals with new friends, laughing and chatting. It’s a great way to meet people while traveling, and also a great Chicago activity to do with friends and partners.

Richard H. Driehaus Museum

• Explore an old mansion to see how the well-to-do lived during the Gilded Age.
• Contemporary art contrasts with old-style luxury and decadence.
• A guided tour is only $5 extra and contributes immensely to the experience.

If you’ve ever wondered what a home looked like in the late 19th century Art Deco period, this is the perfect place to be in Chicago! The museum was once the mansion of Samuel Nickerson and his family, a local banker. Now, after two restorations over the years, it explores the art, design, and architecture of that period to the present.

The permanent collection of period decorative arts suits their surroundings perfectly. Educational and cultural programs contribute to exhibitions which contextualize the Gilded Age and illuminate the vibrant history and culture Chicago.

Enjoy all the little details that make this museum stand out among much larger ones in the country. Each detail is unique, many inspired by locations around the world, others by jazz, music, and the urban culture of Chicago.

Year round the museum features rotating exhibits of modern and contemporary art, which contrasts with the location in interesting and beautiful ways. Spend a few hours here- the more you look, the more you will see.

The staff is also very passionate about their work, and the guides are knowledgeable. In fact, we certainly recommend the guided tour. There’s so much history here, beyond the aesthetic. You will want to learn more about it!

The Museum is located just steps from the Magnificent Mile, and is easy to find! It’s one of Chicago’s lesser-known attractions, so it’s a great place to relax and enjoy the peace.

Mob and Crime Bus Tour

• Hear about how some of the world’s most famous mobsters conned their way through the city
• Ride comfortably in a luxury bus, unaffected by Chicago’s unpredictable weather
• Stake out notorious crime scenes and Chicago landmarks

An alternative way of experiencing Chicago is the Mob and Crime bus tour . It’s not for the faint of heart, though, exploring the sites of Chicago’s most famous and notorious crimes took place. It’s the perfect activity for those rainy or windy days when you can’t explore Chicago on foot.

See famous Chicago crime scenes from the 19th century through to modern times. You’ll learn about Al Capone, the Untouchables, the Chicago Mob, Terrible Tommy O’Connor, the Chicago Black Sox, Leopold and Loeb, Cap George Streeter, and more. You’ll also hear about some of the most daring heists in history!

Visit the historical criminal courthouse, an architectural landmark where some of the biggest cases were tried. Stake out other landmarks and learn about the darker, more criminal side of their history. For a time, gangsters ran Chicago . They are a large and important part of Chicago’s making and rich history.

You will also have the opportunity to leave the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. It’s gory and intense, and a good deal of fun and intrigue.

Watch a Football Game at Soldier Field

• Watch Chicago’s famous sport with enthusiastic fans.
• Enjoy the iconic stadium, which has housed some of NFL’s most famous games.
• More than just sports, you can watch live performances too.

On the third day of your itinerary in Chicago, go watch a football game! Most games are of course played on weekends.  The Bears, Chicago’s local team, have more regular-season and overall wins than any other NFL team. The team and the stadium have a rich history and a loyal following.

Join The Bears’ passionate fans, cheering on the home team, or watch a game with your favorite team! It’s the kind of good sports fun that doesn’t require you to have too much knowledge or enthusiasm for the game itself. Just enjoy the action and the great vibe!

Soldier Field is an iconic football stadium, easy to get around and has lovely, efficient staff. They’re attentive and organized, which is good in a 60,000 seat stadium! Interestingly, it is still the third-smallest stadium in the NFL.

Of course, the stadium also hosts massive concerts, so if you’re more interested in music than sports, have a look at what’s playing when you’re in Chicago .

So how safe is Chicago? Well most of Chicago is very safe for tourists, and you’ll have no trouble walking around and exploring during the day and night. There are, however, some neighborhoods that are better to avoid.

In these areas, gang violence and other criminal activities occur. They are quite clearly sketchy, though, and far from Downtown Chicago where you’ll spend most of your time exploring.

Pickpockets are reasonably common in very busy areas, and we suggest you keep your belongings firmly by your side. Muggings also occur, particularly at night. These can be avoided by staying on well-lit, well-populated streets and avoiding dark or dingy areas. Thieves sometimes operate on the subway, so it’s best to avoid it when out of peak times (7am-9am and 3pm-6 pm).

Neighborhoods to avoid, particularly at night, are the far West Side of Chicago, which has very few tourist attractions and the Fuller Park area. Parts of Downtown Chicago get empty at night, and therefore risky. North Side remains safe throughout the night, and you can walk comfortably here as long as you take the common-sense safety precautions.

Natural hazards do occur occasionally, but their safety risk tends to be low. There is, however, a higher risk during winter.

Don’t Forget Your Travel Insurance for Chicago

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Chicago is near to four different states! You can get to other great cities easily and explore the beautiful surrounding area on these day trips from Chicago.

Chicago to New York City Day Trip by Air

The best of the day trips from Chicago has to be New York by air! Fly to the Big Apple, where you’ll hop on a sightseeing bus and spot the greatest of New York’s world-famous landmarks, like the Statue of Liberty!

The tour is very laid-back, with time to take in a show, do some shopping, or set out on a little extra sightseeing!

The tour includes a round trip from Chicago, a two-course lunch in Times Square, and your sightseeing bus trip. So different to Chicago and yet so close. It’s a fantastic part of the Chicago trip itinerary!

Tour of SW Michigan Wine Country from Chicago

Touring America’s beautiful wine country is the perfect day trip. You’ll tour the scenic countryside and visit three wine farms! Enjoy wine tastings at each of them and a gourmet lunch.

Learn about winemaking and how the grapes in Michigan differ to those found in France’s Napa. Have a delicious meal overlooking a vineyard and enjoy some time walking through and learning about the farms.

The tour includes tastings, lunch, bottled waters, and a departure toast to start things off right! Get to know the people on your tour and enjoy leaving the city behind for a day.

Chicago Grand City Tour & 360 Chicago Observation Deck

This half-day tour of the city is one for the books! Travel through the north and south financial districts, admiring iconic buildings and sculptures. Experiencing the vitality and excitement of Chicago’s central hub.

Enjoy views of Lake Michigan and Jackson Park where the Colombian Exposition of 1893 was held to celebrate the founding of America.

You will also look out from the top of the John Hancock Building, and try to identify all four states! The tour is a great activity to bring friends who only have one day in Chicago.

If you fancy enjoying the windy cities magnificent skyline with a cold (alcoholic) drink, then try to find one of Chicagos rooftop bars – but drink responsibly!

Detroit: The Rise, Fall & Renewal Walking Tour

Fly to Detroit, where you can explore the very different American city with a walking tour before setting out on your own. On the tour, you’ll explore the social and economic upheavals of Detroit through its architectural landmarks, learning all about the city and its complex history!

The tour is a great introduction to the city. You’ll see some of the world’s tallest vacant buildings, and most beautiful modern landmarks. Chat with fellow tourists and a knowledgeable local.

Get tips on where to go next, and source out some of Detroit’s finest food at restaurants like Selden Standard.

Milwaukee Scavenger Hunt Adventure

Catch a short flight to Milwaukee, where you can join an exciting and fun scavenger hunt adventure! One of the best ways to explore the city, you’ll use your surroundings to solve clues and complete challenges.

You can stop and go as you please, and take as much time as you need, admiring and learning about the attractions as you go along. It’s a really laid-back trip, and a great experience for couples, friends, and families.

You use your smartphone to play the game and navigate the historic streets of Milwaukee, enjoying its modern and unique culture.

Stash your cash safely with this money belt. It will keep your valuables safely concealed, no matter where you go.

It looks exactly like a normal belt  except for a SECRET interior pocket perfectly designed to hide a wad of cash, a passport photocopy or anything else you may wish to hide. Never get caught with your pants down again! (Unless you want to…)

Find out what people want to know when planning their Chicago itinerary.

How many days are enough in Chicago?

You’ll want to spend at least 3 days in Chicago, as the city is not very walkable. 4-5 days are ideal for seeing all the attractions and discovering the various neighbourhoods.

What should you include on a 3 day Chicago itinerary?

Don’t miss out on these Chicago highlights: – Millennium Park & Cloud Gate – Chicago Art Institute – Grant Park – Navy Pier

Where is the best place to stay for a weekend in Chicago?

Downtown Chicago is the best place to stay for a short trip. It’s super central, surrounded by the city’s top attractions, and bursting with eateries and nightlife.

What are the best day trips from Chicago?

The Chicago to New York City by Air day trip is the ideal way to spend an extra day. The Detroit Walking Tour and Milwaukee Scavenger Hunt Adventure are also very popular.

With so many world-class museums, sports centers, places of culture, music, food and fun, Chicago is one of the best cities in the world.

You can explore the history of the city, and the natural history of the world! Or stroll through its public parks, and later take in the earth’s most incredible flora. Chicago brings together elements of our whole world in ways unique to the vibrant city.

Even if you’re traveling on a shoestring budget, you can travel to Chicago and make the most of what the city has to offer! With our Chicago itinerary, you will certainly never have a dull moment.

Pack walking shoes, an umbrella, and be sure to bring your camera. You will want to capture the immense skyscrapers as well as the little details that make Chicago iconic!

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

Aiden Freeborn

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That’s a really thorough itinerary, kudos!

Sun Country Airlines is a low-cost airline. The airline offers a range of domestic and international flights to popular vacation destinations at affordable prices. In terms of Sun Country Cancellation Policy it allows passengers to cancel their reservations within 24 hours of booking without incurring any cancellation fees.

YOu should check out the FREE professional Chicago Blues Jam at 9pm at the bar: “West on North.” This is a restaurant bar that 20-30 of the best blues players in Chicago show up to and Jam together. INcredably prepared musicians and nothing is practiced. This is led by singer Ya Ya Townsend. Raw, dirty, improvisation with real heart. The most real Chicago blues fun I have had and the cost for entering $0.

I have always wanted to visit Chicago I’m seriously in love with this type of blog as they highlight all of the best things in every city.

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3 Days in Chicago: The BEST Weekend Itinerary (By a Local!)

Planning 3 days in Chicago and seeking the perfect itinerary? I have lived in Chicago almost my entire life so I have created the perfect detailed Chicago 3 day itinerary with the best things to do, best places to eat, where you should stay, and all of my top tips, so that you can spend less time planning and more time enjoying the Windy City.

There is so much to do in Chicago but three days is enough to see most of Chicago’s top attractions . I have grouped each day by neighborhood so you don’t have to waste time getting around.

3 Days in Chicago Itinerary

3 Days in Chicago – Day 1

Lets start Day 1 in Chicago by enjoying some of the best views Chicago has to offer.

360 CHICAGO

For panoramic views of Chicago, head to 360 CHICAGO (formerly John Hancock Observatory), a public observatory on the 94th Floor of 875 N Michigan that offers breathtaking 360 degrees views of the city skyline and Lake Michigan.

The 360 Chicago observation deck is also home of TILT – Chicago’s highest thrill ride – an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor.

Tip: 360 Chicago tends to be less busy and has shorter lines that the taller Willis Tower (on Day 2) but it is still best to visit in the morning to avoid crowds. (Click here to buy a skip the line ticket ).

Shop (or Window Shop) on the Magnificent Mile

After visiting 360 Chicago, walk south on Michigan Avenue and join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the historic Chicago Water Tower, the Tribune Tower and the Wrigley Building skyscraper.

Take an Architecture River Cruise

Chicago has amazing architecture and the best way enjoy it is by taking an architecture river cruise . Because the water sometimes freezes, river cruises don’t usually run in the winter.

If you are visiting Chicago in the summer, you can do a longer combined architecture river and lake cruise to see the skyline from the lake as well.

An alternative to a river cruise is to take a walk along the Chicago Riverwalk . The Riverwalk is one of the best spots in Chicago for people watching and there are also restaurants , shops and places to sit along the way. You can see a map of attractions on the Riverwalk here .

Go on a Gangsters Tour

Chicago has a long  history of organized crime and is famous for being the home of mafia figure Al Capone. There are many mob tours for those that want to learn more about the history of organized crime.

Food or Drinks with a View

Chicago has several rooftop bars and restaurants with amazing views of Chicago.

Cindy’s (12 S Michigan Ave) is a restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. This is a popular spot and the wait for the elevator can be long but if you visit around the time it opens (10 am on the weekends and 11 am on some weekdays) you can enjoy the great views without the crowds.

LH ON 22 (85 East Wacker Drive) -Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.

The J. Parker (1816 N Clark St) is a stylish bar and restaurant on the rooftop of the Hotel Lincoln with great views of Lincoln Park.

3 Days in Chicago – Day 2

From the highest vantage point of the city to the famous Bean, Day 2 in Chicago will take you to Chicago’s best and most famous attractions.

Skydeck at Willis Tower

The Skydeck at Willis Tower (formerly known as the Sears Tower and what locals still call it) is the most well known of Chicago’s two tall skyscrapers with public observatories. The Willis Tower is the tallest building in the Western Hemisphere and was the tallest building in the world from 1974 until 1998.

If you are not scared of heights, you can stand on the Ledge’s glass boxes that extend out over 4 feet from the Skydeck.

Tip:   Lines for the Skydeck can get very long (especially on weekends) so avoid the crowds it is best to visit first thing in the morning as soon as it opens or in the evening. (Click here to buy a skip the line ticket ).

See The Bean at Millennium Park

If you have seen photos of Chicago on social media, chances are you have seen photos of Cloud Gate (also called The Bean), the famous mirrored sculpture in Millennium Park.

Please note that due to construction, public access and views of Cloud Gate are limited through spring of 2024.

Although The Bean is very touristy, don’t skip it. It is one of the most instagrammable places in Chicago and it is a great spot to take photos to remember your trip to Chicago.  The Bean is usually crowded especially in the summer and on weekends so if you don’t want other people in your photos visit early in the morning.

The free Millennium Park is part of Grant Park and also includes the Jay Pritzker Pavilion, the Crown Fountain sculpture and Lurie Garden. In the winter, there is a free ice skating rink right in front of the park. On hot summer days, kids (and some adults) love to splash in the water from the Crown Fountain .

If you are visiting Chicago with toddlers and young kids, you might want to also visit Maggie Daley Park , a large public park connected to Millennium Park that has play areas for kids of various ages, a fieldhouse, climbing wall and another ice-skating ribbon in the winter.

Art Institute of Chicago

Chicago has many great museums which are worth visiting but my top pick is the  Art Institute of Chicago conveniently located next to Millennium Park. It is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. (Click here to buy a skip the line ticket if you want to avoid long lines).

Some locals consider Navy Pier a bit of a tourist trap, but it is a not to missed attraction especially for those visiting Chicago with kids. Navy Pier is full of fun things to do including a large Ferris wheel, rides and games, the Chicago Children’s Museum and several shops, restaurants (including Giordano’s and Garrett Popcorn Shops) and bars. Navy Pier is also the starting point for various sightseeing cruises and boat rides.

Tip: If you are visiting Chicago in the summer, stay or come back for the free fireworks at Navy Pier every Wednesday at 9 pm and Saturday night at 10 pm. You can even watch the show from the water on a sightseeing cruise .

3 Days in Chicago – Day 3

Here are my suggestions for your third and final day sightseeing in Chicago. If you are visiting Chicago on a Sunday morning, head to Maxwell Street Market , one of the best places for Mexican food.

Visit One or More Museums

Chicago has many great museums which are worth visiting. The Field Museum , the  Shedd Aquarium and Adler Planetarium are all located close to each other on The Museum Campus. The Adler Planetarium Skyline Walk has one of the best skyline views of Chicago .

The Museum of Science and Industry is located in Hyde Park and is a bit out of the way from downtown Chicago but it is a really fun museum with hands-on activities and interactive exhibits. If the weather allows and you have extra time in Hyde Park, you might want to check neighboring Jackson Park . This park has cherry blossom trees in the spring and it also has a free Japanese garden.  Promontory Point is about a half mile away and has great skyline views of Chicago.

Tip:   If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.

Explore the Lakefront Trail and Beaches

Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan and it is a great spot to people watch and get some exercise.  In the summer and weekends, the lakefront is packed with locals and visitors walking, running and riding bikes.  You can find a map with the access points here .

Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan.   Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions. North Avenue Beach is more of a party beach and is located close to Lincoln Park.

More Things to Do in Chicago

If you have more time or not a fan of museums or tall buildings, here are some more fun things to do in Chicago:

Find Street Art

Chicago is full of street art and there are always new murals popping up.  One of the most famous Chicago murals is “Moose Bubblegum Bubble” (pictured above) by Jacob Watts which located at 33 E. Ida B. Wells Drive (formerly 33 E. Congress Parkway). It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions. You can find more detailed mural walks in the Loop here .

Another famous mural is The Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour .

Another neighborhood that has a high concentration of street art (as well as great Mexican food) is Pilsen.

Watch a Cubs Game at Wrigley Field (or attend another sporting event)

Chicago is known for their love of their sports teams, so if you are visiting during the season you might want to attend a sporting event. To those unfamiliar, historic Wrigley Field is home to one of the city’s baseball teams – the Cubs.  Whether a fan of the Cubs, baseball in general or just a fun atmosphere, a day at the 100 year old ballpark is a must for locals and tourists alike.  You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere while drinking and eating. (There are also tours of the stadium offered during the off season).

Enjoy One of Chicago’s Many Festivals

Chicago always has at least one or more festivals or events happening every weekend especially in the summer .  Some Chicago festivals are very well known and attract thousands of tourists, but there are many festivals and events in Chicago where you will mostly find locals. For great food, music and people watching, check to see if there are any festivals or events  going on while you are in town.

Walk The 606

The 606 is Chicago’s version of The Highline in NYC , an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square.  It is a bit off the beaten tourist path but it great place to walk, run or bike.  There are several access points so you can get off the trail to explore the various neighborhoods.

Where to Eat in Chicago

Chicago is known for its food so get ready to eat! Chicago is one of the best cities in the world for food and I could easily write a whole post just about the food! Although Chicago is famous for food like deep dish pizza and Chicago-style hot dogs – there is so much more great food in Chicago.  Don’t limit yourself to just deep dish pizza and hot dogs, but you should try those if you are visiting Chicago for the first time.

Lou Malnati’s and Giordano’s  are two of the best restaurants for deep dish pizza. Giordano’s can be found in several spots throughout the city including Navy Pier, near Michigan Avenue and near Millennium Park.

Many locals consider Pequods in Lincoln Park to have the best deep dish pizza in Chicago. Their version has a caramelized crust.

For Chicago style hot dogs (remember, no ketchup allowed) try Portillos , a popular chain.

Al’s Italian Beef (169 W Ontario St.) is famous for its Italian beef sandwiches.

For original Chicago-style popcorn head to Garrett Popcorn Shops, with a location near Millennium Park and Navy Pier.

To get an overview of the food scene consider a food tour:

Where to Stay in Chicago

Most people visiting Chicago stay in the downtown area including the Loop, River North, Gold Coast, Streeterville and Michigan Avenue since they are close to most of the major tourist attractions. If you are visiting during the weekend, the Loop is a great option as it is more quiet at night. River North (where I live) is close to nightlife and restaurants, but noise can be a problem especially during the weekends. Here are some of my top picks for the best hotels in Chicago :

The Peninsula Chicago.   If you are looking for a luxury hotel, The Peninsula Chicago is one of the best hotels in Chicago with a world renown spa and a half-Olympic length swimming pool overlooking the Chicago skyline. It has a central and convenient location right off the Magnificent Mile, close to shopping and less than a block from the Water Tower and 360 Chicago. Click here to see the latest prices and click here to read reviews .

Hilton Chicago/Magnificent Mile Suites.  Recently renovated all-suite hotel with fridge and microwave in room. Great location just steps from Michigan Avenue and one block from Lake Michigan.   Click here to see the latest prices and click here to read reviews .

ACME Hotel Company. This modern, stylish and unique hotel is located in downtown Chicago 2 ½ blocks from the Magnificent Mile in River North. Offers great value and great service. Click here to see the latest prices and click here to read reviews .

Best Western River North Hotel. Convenient located in the heart of River North close to the Chicago River as well as many restaurants and bars. Amenities include free high-speed Wi-Fi, deeply discounted parking, room service, fitness center, indoor pool and sun deck.  Click here to see the latest prices and click here to read reviews .

The Best Time to Visit Chicago

Chicago has plenty of things to do year round whatever the season. Summer is one of the best (and busiest) times to visit Chicago as the city comes alive and there are always outdoor festivals, concerts and events going on where you can take advantage of the warm weather. Restaurants and bars open their rooftops and sidewalk patios so you can dine outside. The temperature in the summer is usually hot but not unbearable (but some days can be very hot and muggy).

Winter can be very cold and snowy but some years can have mild winters with hardly any snow. Late November and December are busy with holiday events and festivities and the temperatures are usually still not that cold.  January and February tend to be the coldest months but attractions are less crowded. Even if you hate cold weather, there are enough indoor attractions to keep you entertained in Chicago during the winter .

Fall and spring are generally great times to visit Chicago – the popular attractions are not as busy as summer and the weather is usually more pleasant (but temperatures can be very unpredicable). The weekend before St. Patrick’s Day and the weeks during spring break can get very busy but the rest of spring is considered shoulder season.

Personally, I think the best time to visit Chicago is September and early October because students are back in school but temperatures are still warm but not as hot and humid as summer.

If you still need help deciding when to visit Chicago, check out The Best Time to Visit Chicago – A Month By Month Guide  for more details regarding weather and events by month.

Getting Around in Chicago

Chicago is an easy city to get around in with many public transportation options. Both Chicago airports – Chicago O’Hare (ORD) and Chicago Midway (MDW) – are connected to downtown Chicago by train.

For longer distances you can use public transportation , taxi, rideshare or rent bikes through Divvy (Chicago’s bike share program).

Taxis are plentiful and very easy to find downtown and at popular tourist attractions. You can also use the Curb app (for taxis) or ridesharing apps ( Lyft and Uber) to get around Chicago .

A hop on hop off bus is a great way to see all the attractions without having to figure out how to get around.

These are my top choices for the best things to do if you have 3 days in Chicago .

Planning a trip to Chicago? Check out more of my Chicago guides and itineraries:

• Best Things to Do in Chicago in the Summer
• 24 Hours in Chicago: A Perfect One Day Itinerary (From a Local)
• Most Instagrammable Places in Chicago
• Best Free Things to Do in Chicago
• Best Day Trips From Chicago

Related Posts

savvyglobetrotter

One comment.

Hi, I have also lived in Chicago and yes, although Summer is great, the best time to visit I’d also say it’s Aug/Sept. This is one, if not THE one, of the best places on Earth. I’d even say, if you can stay longer than 3 days in Chicago, do so. You are not going to regret it, since the city offers so much to do year round. Lovely post!

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3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary

Chicago is a vibrant city that feels very alive, and with the perfect 3 days in Chicago itinerary, it’s possible to sample the best of the city over a long weekend!

The city is always on the move, and there isn’t an hour in the day that you won’t find at least 10 unique and adventurous things going on around town.

Music and food festivals pull out all the stops in Chicago, on top of the arts and cultural events that dot the city throughout the year.

Are you into food and drinks, lake views, and most of all, fun? Then Chicago is the place to be. There is enough here to explore for months, and we are going to pack all of the best events and activities into a 3 day long weekend itinerary to experience the essence of Chicago. 

Note: this Chicago blog post was written for Our Escape Clause by former Chicago locals Zach & Julie Ruhl, the travel couple behind Ruhls of the Road . Thanks for joining us, guys!

Table of Contents

Day 1 in Chicago Itinerary: The Bean, Skydeck & Great Chicago Food

Day 2 in chicago itinerary: lincoln park, wrigley field & beyond, day 3 in chicago itinerary: magnificent mile, navy pier & an afternoon adventure, where to stay for 3 days in chicago, where to eat during your chicago weekend getaway, getting around during 3 days in chicago, when to spend a long weekend in chicago.

Some links in this post may be affiliate links. If you make a purchase through one of these links, we may earn a small commission at no extra cost to you. Please see our disclosure policy for more detail.

Chicago is an enormous place. The city covers miles in each direction, with awesome things to do located all over the map. Therefore, this Chicago itinerary is going to thoughtfully take you from place to place, minimizing travel time and maximizing adventure.

Your first day in any new city should no doubt include some of the most signature sightseeing highlights there–and this Chicago itinerary is no exception, starting with a popular activity that is relatively new in Chicago: the Riverwalk. The current version of the Riverwalk was completed in 2017 and is an excellent place to start your Chicago weekend getaway.

Start your weekend in Chicago with a walk on the Chicago Riverwalk.

The Chicago Riverwalk starts at Wolf Point, near where the Chicago River turns from East/West to North/South. From there, the Riverwalk continues for over a mile, to the point where the Chicago River meets Lake Michigan.

Along this beautiful walk, you’ll pass a few awesome cafes and restaurants. This is a great place for a morning coffee, watching the morning hustle and bustle of America’s third-largest city. On top of that, the morning walk counts as your exercise for the day!

If you fall in love with the Riverwalk, then come back for a happy hour one evening. Riverside wineries and bars open up during the evening, complete with sets of outdoor games, live music, and some great entertainment! 

Check out Millennium Park.

At the end of the Chicago Riverwalk, you’ll reach Lake Michigan. Turn right here and head South to Millenium Park, where you’ll find an excellent location for soaking in the Chicago skyline from a beautiful park in the huge city center.

Millennium Park is an awesome Chicago sightseeing destination for two reasons. First off, it is just a great park full of fun things to do in Chicago !

There is an awesome playground for kids to play on, a great dog park for your four-legged friends, a huge green space to sprawl out for a picnic, a live music amphitheater, the Crown Fountain with a reflecting pool, endless gardens, and so much more!

You could spend a whole day at Millenium Park and not grow bored.

The second reason Millenium Park is so great is its proximity to everything. The park is great, but what makes it so impressive is that you are literally in a natural oasis amidst the concrete jungle of downtown Chicago.

Look around you while in the park, and you’ll see the towering structures of the Willis Tower, the Aon Center, and the rest of the enormous Chicago skyline.

Snap photos at The Bean.

At the edge of Millenium Park is The Bean, AKA Cloud Gate, Chicago’s most photographed (unofficial) monument.

The Bean is a huge monument, standing over 30 feet tall and 60 feet long, that is made of polished chrome and has no visible seams. This structure is truly unique and is an awesome downtown Chicago sight. 

The Bean is perfectly reflective, and due to its shape, the reflections can make for very fun images. It is essentially a gigantic magic mirror, placed in the middle of a bustling downtown environment.

Spend some time enjoying the fun reflections you can see as you walk in a circle around and under The Bean, then head for some food.

Downtown Chicago should have plenty of options on your way to your next stop: the Willis Tower. 

Admire views of Chicago from the Willis Tower Skydeck.

The Willis Tower is Chicago’s tallest building and the second tallest in the United States. At one point, this skyscraper was even the tallest building in the whole world, and held that title for 25 years! There’s no doubt that this is a must-see spot on any 3 day Chicago itinerary.

When you visit the Willis Tower, there are really two things you need to do. First off, admire the size of this monstrosity from below. The building literally reaches into the sky, and from the bottom seems impossibly huge. Walk around it marveling upwards, just make sure to lose your attention and wander into the city streets!

The other way to see the Willis Tower is, of course, from the top. The Skydeck is at the very top of the building, where you can see Chicago stretch beneath you for miles and miles in each direction into the horizon.

If you have the stomach for it, there is even a glass-bottomed section where you can literally step out into the sky, or at least it looks that way. From the glass floor, you can see down over 1,000 feet to the streets beneath you. This is quite an incredible experience and one that you won’t get anywhere else in the United States!

Book your Skydeck tickets for the Willis Tower today!

Finish your first day in Chicago in West Loop on Randolph.

The West Loop is an up-and-coming neighborhood in Chicago. This area seemingly has a great new restaurant pop up each week and has some of the most delicious food and one of the most fun atmospheres in the city.

Randolph Street in the West Loop is the culinary center of the neighborhood and is where you should head for dinner and drinks on your first day in Chicago. If you have the time and energy, the very best activity is to have a drink at a few different places, hopping from place to place and soaking up as much of this wonderful neighborhood as you can.

Each restaurant will have a unique vibe and atmosphere, so keep hopping around until you find the one you love best.

Want to make sure you experience the best food in the neighborhood? Add this popular West Loop Food Tour to your Chicago itinerary!

Close out your first night in Chicago at an Irish pub.

Chicago has a huge Irish population, and therefore quite a few Irish pubs located around the city. Our best recommendation is to find one close to your hotel and pop in for a Guinness as a night-cap. Enjoy the Chicago atmosphere, and then head to your hotel to get some sleep before heading off on your second day’s worth of fun things to do in Chicago!

Day 2 in Chicago is going to be a day full of exploring Chicago’s famous North Side. The North Side is awash with classic Chicago food options (Chicago loves its food…) as well as awesome sites to see and things to do. First up is the famous Lincoln Park.

Start the day with a stroll through Lincoln Park.

Lincoln Park is a huge and sprawling greenspace alongside Lake Michigan for 7 long miles. This is, in fact, the largest park in all of Chicago! And it also may very well be the most beautiful.

Alongside Lake Michigan, Lincoln Park has a few different beaches, as well as seemingly endless biking and walking trails. If you would rather bike than walk, then there are many bike rental options scattered all around the park, and around Chicago as a whole.

While strolling or biking through Lincoln Park, make sure to stop and see the Belmont Rocks, North Pond, and the Signal of Peace Monument. Along the way, admire the natural beauty and enjoy the sounds of birds singing as you bring on your second day in Chicago.

Soak up the sun at North Avenue Beach.

North Avenue Beach is one of Chicago’s largest and most popular beaches. Located right alongside Lake Michigan, this vast expanse of white sand makes for a great place to enjoy the beautiful Chicago summer sun.

If you are traveling with a group, then there are opportunities for some beach volleyball at North Avenue Beach! At the beach, you can rent a net and a ball (rentals are by the hour) and play some volleyball on the sand in view of the Chicago skyline!

While at North Avenue Beach, you must make a stop at the famous beach house that is shaped like a boat. This is also the location of Castaways, a bar and grill on the roof of the beach house serving yummy drinks with an incredible view. 

Head to Wrigley Field & Wrigleyville.

You can’t visit the North Side of Chicago and not see Wrigley Field. As one of the most famous baseball stadiums in existence, and the home of the Chicago Cubs, this is a must-see stadium, especially for sports fans.

Wrigley Field is located right in the heart of Wrigleyville on the North Side. Surrounded by residential areas and a huge bar and restaurant scene, this area is a magnet for good times, especially when the hometown Cubs are lacing up their cleats for a game.

If you are fortunate enough to be in Chicago while the Cubs are playing, head to Wrigley just for the experience of people watching and cheering on the hometown team. If you’d like, you could even try and buy some tickets, and usually, you can get a good deal on seats if you are okay purchasing them after the game is already in the 2nd or 3rd inning.

Wrigleyville, the neighborhood surrounding Wrigley Field, is an excellent place to hang out, have a drink, and hop around a few of the local establishments. Each of them has a great atmosphere, delicious, food, and of course a wide array of beers on tap.

Sample some Malort.

Malort is a Chicago specialty liquor and is something anyone over 21 should try when they visit the Windy City.

The liquor itself is not good because of taste, in fact, it tastes pretty bitter, and most people find it awful. However, it is all about the experience of trying something the locals love! If you’d like to experience the local culture of Chicago, then you have to try Malort at least once.

Finish the Day at the John Hancock Center Signature Lounge.

The John Hancock Center is the best building in Chicago. That may be a controversial opinion, but it is so true. The enormous slanted walls of the Hancock reach over 1,000 feet into the Chicago sky, with huge beams in a crisscrossing X pattern the entire way up. The building is an architectural masterpiece and is a wonder to see from the base.

The best place to experience the Hancock Center, however, is not from the base. It is from the Signature Room.

What is the Signature Room? It is an incredible 95th-floor bar and restaurant with an absolutely stunning view of Chicago. The Signature Room offers a 360-degree view of Chicago from above and is especially breathtaking as the sun sets and the sea of lights emerges beneath you.

Experiencing an evening at the Signature Room is a wonderful experience, and will be a highlight of your visit to Chicago. If you are visiting on a budget, just order a drink here, as dinner can be expensive!

Day 3 is going to be spent exploring more awesome sites and destinations in downtown Chicago. It is going to be a day where you can see as much as you want, and take it all in at your own pace. Choose your own adventure and make today special as you finish up your long weekend in Chicago!

Walk down the Magnificent Mile.

Start the day with a trip down the Magnificent Mile. This is a section of Michigan Avenue that is the retail center of Chicago. The street is lined on both sides with tons and tons of flagship stores, boutiques, and shopping malls.

Along the Magnificent Mile, in addition to all of the premier shopping, there are a few awesome sights you’ll see during this part of your Chicago weekend getaway.

The Wrigley Building is an awesome structure located right where Michigan Avenue meets the Chicago River. The Tribune Tower and the Chicago Water Tower are also wonderful landmarks along this stretch.

Explore Navy Pier.

Just a few blocks from the Magnificent Mile is Navy Pier, an absolute must-visit destination on any Chicago visit. The Navy Pier is, as the name suggests, a large pier, formerly used by the Navy, that extends straight out into Lake Michigan. 

These days, Navy Pier is an awesome destination that is used for a wide variety of attractions. First off, there is almost always some form of live entertainment or shows that are happening over a weekend at Navy Pier. On top of that, the pier is lined with awesome bars and restaurants, as well as shops and boutiques.

The view from the end of Navy Pier is excellent. First off, you’ll get to see the vast expanse of Lake Michigan on 3 sides of the pier. However, when you look back at the city, you’ll get a view of the full skyline including the Willis Tower and the Hancock Center. Do you want an even better view? Because there is one way to get it… There is a HUGE Ferris wheel that you can ride to get a stupendous view of the entire Chicago skyline and Lake Michigan!

Visit Buckingham Fountain in Grant Park.

After exploring Navy Pier, head to Grant Park, another of Chicago’s excellent downtown parks. Here you’ll have the chance to explore a huge area of green space, complete with monuments, statues, and a great lakeside walkway. At the heart of Grant Park, you’ll see Chicago’s most famous and beautiful fountain: Buckingham Fountain

Buckingham Fountain is at the center of Grant Park and is a great place to sit and enjoy a coffee or picnic. The fountain itself is beautiful, but it is made even better by the great Chicago skyline in front of you, and Lake Michigan behind.

Further South in Grant Park you’ll find three other excellent Chicago sightseeing spots to consider adding to your 3 day Chicago itinerary:

Field Museum, Shedd Aquarium + Adler Planetarium

On the south side of Grant Park are 3 beautiful buildings, each of which houses an awesome adventure. The Field Museum is one of the largest natural history museums in the world and is home to some of the best exhibits you can possibly imagine. When we visited in the past, the dinosaur exhibit left us astounded, as they had a full-size Tyrannosaurus Rex named Sue!

The Shedd Aquarium is a world-class aquarium located just east of the Field Museum on Lake Michigan. This aquarium is stunning both from the outside and inside and offers hours of exploration as you make your way through the grounds.

Finally, the Adler Planetarium, America’s FIRST planetarium, is a wonderful place. This place offers the chance to explore things that are out of this world, literally. If you are at all interested in space, astronomy, or astrophysics, then you will have the time of your life at the Adler Planetarium.

Finish your long weekend in Chicago at River North.

River North is the area just north of the Chicago River. Whoever named it wasn’t very creative, but they were very accurate.

River North is absolutely FULL of awesome bar and restaurant destinations. As with many neighborhoods in Chicago, the best way to experience it is by hopping from place to place. When you find a place you love, stay as long as you’d like, then move along to the next place! That is the Chicago way of experiencing the nightlife.

Chicago is an enormous place, sprawling for miles and miles. The downtown area has many neighborhoods, each of which has pros and cons for visitors to the Windy City.

The best places to stay for 3 days in Chicago are near the Chicago River, specifically River North, Gold Coast, Streeterville, and The Loop.

In addition to those, a few more great neighborhoods are Lakeview, Lincoln Park, West Loop (which is home to great Chicago street art ), Near North, and Old Town.

Here are a few great hotel recommendations for budget, mid-range, and luxury travelers.

Godfrey Hotel — The Godfrey Hotel is in the River North neighborhood, and is right in the middle of many of the best activities on your 3 day Chicago itinerary. On top of the great location, the hotel is beautiful on the inside and gets excellent reviews. The Godfrey Hotel is a wonderful place to hang your hat while exploring Chicago.

Check rates & book your stay at The Godfrey Hotel today!

Hyatt Regency Chicago — The Hyatt Regency Chicago is located in The Loop neighborhood, right on the Chicago River.

Many of the rooms in the Hyatt Regency have beautiful views of the Chicago River, the skyline, and the city streets.

The rooms are wonderful, the price is good, and the location is excellent. Additionally, the fitness center, meeting rooms, an on-site bar and restaurant, and access to Chicago activities make the Hyatt Regency one of the best places to stay in Chicago.

Check rates & book your stay at the Hyatt Regency Chicago today!

The Langham — Now, to the creme de la creme. If you’re a luxury traveler looking for the best hotel in Chicago, look no further than The Langham.

First off, the location could not be better. Located right on the Chicago River in River North, you’ll be within walking distance of nearly everything on your itinerary.

Additionally, The Langham pulls out all the stops when it comes to amenities. The on-site spa, fitness center, pool, and deluxe bar and restaurant are all five stars. Of course, the rooms are wonderful as well, and nearly all have stunning views of the cityscape.

Check rates & book your stay at The Langham today!

Chicago and food go hand in hand. You could explore a new food destination in Chicago every night for the rest of your life, and not eat at the same place twice. Not going to fact check that, but it is probably true. There are awesome restaurants on every corner, all across the city!

Here are four must-visit restaurants in Chicago that we love. 

Chicago-Style Pizza – Giordano’s

You can’t come to Chicago and not try some Chicago-style pizza. You literally can’t, it is impossible. The best Chicago-style pizza is at Giordano’s. The pizza here is absolutely LOADED with cheese and toppings, more than you have ever had, guaranteed. One slice and you’ll be satisfied, two slices and you’ll be stuffed. Be prepared to have leftovers!

Portillo’s is a Chicago institution. This started as The Dog House, a hot dog stand, and grew into Portillo’s, a delicious restaurant serving beef, burgers, and Chicago-style hot dogs all across the city. Portillo’s is yummy, quick, and is a Chicago must. Try the chocolate cake shake, you’ll be glad you did.

Happy Camper

Happy Camper is an excellent classic pizza place located in the Near North neighborhood, which offers an excellent atmosphere. This is a great place to watch sports, meet friends, enjoy a happy hour, and of course, try some pizza!

The toppings are creative at Happy Camper, and the pizza is DELICIOUS. There is also a huge selection of local and imported beers to try.

Girl and the Goat

Girl and the Goat is an absolutely EXCELLENT restaurant located in the West Loop neighborhood on Randolph Street. T he food here is delicious and is very creatively and expertly prepared.

Call ahead for a reservation at Girl and the Goat, as there may be a long wait if you just show up asking for a table. If you do just show up, however, this is worth the wait.

And you can walk across the street to one of the many bars on Randolph while you wait for a table at Girl and the Goat!

Bonus: take a Chicago food tour!

In a city as centered around food as Chicago, taking a food tour is one of the best ways to explore the city’s cuisine. 

Not only will you be able to sample a wide variety of classic dishes without committing to a whole portion, you’ll also learn plenty about Chicago’s history and culture along the way!

This popular food tour gets rave reviews and is an excellent addition to your long weekend in Chicago.

Book your food tour in Chicago today!

Getting around for 3 days in Chicago is in most ways easy, but can sometimes be challenging.

The public transport system is the easiest and most inexpensive way to get around, followed by cabs/Uber/Lyft, and finally driving yourself.

Much of the 3 days in Chicago itinerary laid out above, however, can all be completed by exploring on foot, especially from the recommended hotels. The awesome destinations and great parks are relatively close together and can be reached with a nice walk in the Chicago air.

Chicago has one of the best public transport systems in the US. The elevated train, AKA the ‘L’, brings people across Chicago east, west, north, and south. The ‘L’ stops at all of the amazing sites in the city, as well as O’Hare Airport, Midway Airport, and all the major thoroughfares.

If you would rather avoid public transportation, then the best way to travel around during this 3 day Chicago itinerary is with a cab/Uber/Lyft. Traveling this way is likely the fastest if you can avoid rush hour, and the most convenient. However, it will be more expensive than using the ‘L’ trains.

Finally, you, of course, have the option of driving yourself around town. In our opinion, this is the most stressful way to get around, as you’ll have to worry about parking in the busy downtown streets. This is a challenge and is made worse considering that many hotels offer parking fees.

The best time to plan a long weekend in Chicago is during the summer. The weather during the summer is absolutely perfect, and it’s definitely the easiest time to pack light for a Chicago vacation (if you visit during the blustery winter, be sure to carefully consider what to wear in Chicago !). This is also the best time to explore the awesome parks, beaches, and outdoor destinations in the Windy City.

Each year in the summer, Lollapalooza brings huge crowds looking for an awesome time and great music. Lollapalooza draws many of the best music acts in the world, so traveling to Chicago during the music festival is a great opportunity. On top of this festival, many great music artists perform regularly at Wrigley Field, Soldier Field, the United Center, and the other great venues across Chicago.

Coming in a close second to the Chicago summer is the spring when the city defrosts after its long Chicago winter and comes alive. There is nothing quite like spending 3 days in Chicago when the atmosphere is on the rise, as it is in spring.

Also during this time is St. Patrick’s Day, one of the largest holidays in Chicago. On St. Patrick’s Day the river is dyed bright green, and the partygoers are out in force.

4 thoughts on “3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary”

I’d like to follow for future information

Thanks for this comprehensive guide! It made planning a trip to Chicago so much easier!

As a frequent traveler to Chicago, who lives just a few hours away, I want to mention a few places that truly make Chicago iconic. The Palmer House Hotel is the best in the City. Right outside the doors of the Palmer House is a Chicago favorite, with a long history, called Miller’s Pub. Grab an Allagash White beer on tap – a local favorite. Don’t miss a food tour of Chinatown. There is so much history there, and the food is really amazing! Other amazing foodie spots in Chicago are Bongo Room for brunch and Cafe Babareba for Spanish style tapas (do not miss the baked goat cheese in tomato sauce). An architectural tour on the Chicago River is a lovely way to spend the day and if that isn’t your thing, the water taxis are a fun way to get around.

Agrred with the other poster–This itinerary is hugely missing the architecture tours! Best thing to do in the city. River north is fine, but kind bro-y for lack of a better descriptor. Bongo room is in Wicker Park which I describe as our Williamsburg. Not quite as artsy and cool as it was 5 years ago but still very fun!

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Chicago   Travel Guide

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3-days Itinerary in Chicago

• 3-Day Itinerary
• All Things To Do
• 1-Day Itinerary
• 2-Day Itinerary

Art Institute of Chicago Art Institute of Chicago

Home to one of the country's most impressive collections of impressionist and post-impressionist art (plus works from numerous other genres), the expansive Art Institute of Chicago features nearly 300,000 works from all over the world in its permanent collection. You'll find pieces created in the Byzantine era, as well as paintings completed just a few decades ago. Highlights include Jacob Lawrence's "The Wedding," Georgia O'Keeffe's "Sky above Clouds IV" and Grant Wood's "American Gothic." The Art Institute's exhibits also include all sorts of intriguing artifacts, from European armor to the Thorne Miniature Rooms, which showcase interior design and furnishings in Europe and America from the late 13th to early 20th centuries. In addition to the permanent collection, the Art Institute hosts traveling exhibitions covering a variety of subjects and showcasing a diverse array of artists and genres.

The Art Institute of Chicago earns high praise from recent visitors, thanks in part to its impressive collection. Art enthusiasts particularly commend the museum's impressionist collection, which features pieces from famous artists like van Gogh, Monet and Renoir.

Millennium Park and Cloud Gate Millennium Park and Cloud Gate free

U.S. News Insider Tip: Construction around the Cloud Gate sculpture will limit the public's access to this top tourist attraction until spring 2024. While you might not be able to snag a selfie with "The Bean," many other attractions are available within the park. – Cortney Fries

A first-time visit to Chicago isn't complete without a stop at Millennium Park. Situated in the Loop just north of the Art Institute of Chicago , this 25-acre space is used to showcase cutting-edge art, architecture and landscaping; it also acts as a backdrop for concerts and festivals. Most visitors come to Millennium Park to see the Crown Fountain and Cloud Gate, better known as "The Bean." Designed by Spanish artist Jaume Plensa, the Crown Fountain features two 50-foot towers that face each other at opposite ends of a shallow reflecting pool. The towers' LED screens project the faces of 1,000 different Chicago residents, which are perfectly aligned with spouts so that it appears they are spitting water on passersby. The water flows mid-spring through mid-fall, while the faces are projected year-round. Cloud Gate – created by British-Indian artist Anish Kapoor – is a 110-ton bean-shaped sculpture forged from stainless steel. The Bean's elliptical shape reflects the Chicago skyline. A quintessential Chicago souvenir is a photo of your reflection in The Bean.

Chicago Architecture River Cruise Chicago Architecture River Cruise

A visit to 360 CHICAGO or Skydeck Chicago will give you a good overview of the city's layout. But if you want to learn more about Chicago's sky-high buildings, tag along on an architecture river cruise. During a river cruise, you'll gain great views and historical insight about well-known structures like the Wrigley Building, the Leo Burnett Building and the Fulton House.

Though several companies, including Wendella Sightseeing Co. and Chicago Line Cruises, offer architecture river cruises, most travelers recommend climbing aboard a Chicago's First Lady Cruises boat with a Chicago Architecture Center docent. You'll learn tons of information about the area's architecture, plus catch superb skyline photo-ops.

The Magnificent Mile The Magnificent Mile free

U.S. News Insider Tip: The Magnificent Mile, known for its world-class shopping, also has plenty to offer architecture buffs. Book a walking tour with the Chicago Architecture Center and hear the untold stories of North Michigan Avenue's architectural icons. Tours start at $30. – Sarah Estime

For shopping at more than 450 retailers within walking distance in downtown Chicago, make your way to The Magnificent Mile. This portion of Michigan Avenue – which stretches between Lake Shore Drive and the Chicago River – beckons to shopaholics with department stores and luxury retailers like Bloomingdale's, Marcus, Macy's, Tory Burch and Nordstrom. Additionally, The Magnificent Mile is home to several top-notch eateries and luxury hotels, including The Drake , the Sofitel Chicago Magnificent Mile and the InterContinental Chicago Magnificent Mile .

360 CHICAGO Observation Deck 360 CHICAGO Observation Deck

One of Chicago's most notable attractions is its skyline, and one of the best places to experience it is at the 360 CHICAGO Observation Deck. Formerly known as the John Hancock Observatory, 360 CHICAGO towers 1,000 feet over The Magnificent Mile from its location on the 94th floor of the John Hancock Center (or 875 North Michigan Avenue as its more formally known). Encased by floor-to-ceiling windows, 360 CHICAGO boasts expansive views of the city; on a clear day, you can see four states. Meanwhile, the interactive screens will help you identify different landmarks that appear in your panorama.

For a different point of view (and an adrenaline rush), test out 360 CHICAGO's TILT. In this mechanized room, visitors hold on to handlebars as the top of the room's windows extend outward, tilting you toward bustling North Michigan Avenue down below. For another memorable way to immerse yourself in the views, try ClouldWalk, a 3D art experience introduced in 2022. Mural artist Nate Baranowski created an optical illusion on the observation deck that makes visitors feel as though they are standing on a crane platform in the clouds.  Should you prefer to experience the view without feeling your heart skip a beat, grab a cup of coffee, a glass of wine or a snack at the cafe and bar, or look for souvenirs in the gift shop.

Grant Park and Buckingham Fountain Grant Park and Buckingham Fountain free

U.S. News Insider Tip: If you're visiting Chicago Sept. 8 through 10, head to Grant Park early – around 11 a.m. to avoid the lines – for the Taste of Chicago. Enjoy the park and eat the best cuisine the city has to offer. Admission is free. – Sarah Estime

Often referred to as "Chicago's front yard," Grant Park is an approximately 313-acre swath of green space that starts at the eastern edge of the Loop and stretches down to the northern fringes of the Near South Side. First-time visitors should plan on spending a fair amount of time in Grant Park: This is where you'll find several of Chicago's most popular things to do, including The Field Museum , the Art Institute of Chicago and Shedd Aquarium . ( Millennium Park also rubs elbows with the northwest corner of Grant Park.) Baseball diamonds, flower gardens, walking paths and wide-open grassy terrain are available as well.

The Field Museum The Field Museum

U.S. News Insider Tip: After hours of museum hopping, grab a kid-approved lunch at Kim & Carlo's Hot Dog Cart. The no-frills stand offers everything from vegan dogs to the traditional Chicago hotdog. Enjoy your lunch on the water. – Sarah Estime

This extensive natural history museum occupies half an acre of Grant Park 's Museum Campus and houses exhibits that showcase artifacts from multiple eras and destinations, making it a must-see for kids (as well as any fans of the "Indiana Jones" movies). Some of the most popular parts of the museum include the "Inside Ancient Egypt" exhibit, which features a reconstruction of a three-story replica of an Egyptian tomb, one of the largest collections of mummies in the United States and interactive representations of life on the Nile. There's also the Restoring Earth area in the Abbott Hall of Conservation, where visitors can learn more about sustainability through hands-on activities. But no visit to The Field Museum would be complete without some quality time with SUE, the facility's T. rex who just happens to be the largest, most complete T. rex ever discovered. SUE is 40 feet long from nose to tail and boasts 55 terrifying teeth.

Shedd Aquarium Shedd Aquarium

U.S. News Insider Tip: If you're visiting in the summer (June through August), check out Jazzin' at the Shedd. You can enjoy jazz music and drinks with incredible views from the terrace. Plus, the lights dim in the aquarium for a unique experience. – Elizabeth Von Tersch, Senior Editor

Shedd Aquarium is one of the world's largest indoor aquariums, housing around 32,000 creatures. While you're here, you can feel stingrays float beneath your fingers, listen to sea lions bark and learn all about a variety of turtles. A visit to Shedd Aquarium will lead you through a cornucopia of habitats, where you'll find additional animals like penguins, piranhas, sharks and beluga whales. Or, for an additional fee, you can participate in specialty experiences like animal encounters, feeding experiences and virtual reality.

Navy Pier Navy Pier free

Extending out onto Lake Michigan, Navy Pier offers plenty in the way of family-friendly entertainment. The first thing you'll spot once you set foot on the pier is the towering Ferris wheel (which stands 196 feet tall); you'll also find a drop tower and a carousel. Once the kids have had their fill of thrill rides, you can spend some time cruising the Chicago River on a sightseeing or speedboat tour or spend a few hours exploring the Chicago Children's Museum , with hands-on exhibits ranging from treehouses to fire trucks.

But you don't have to be a kid to enjoy a visit to Navy Pier. Grown-ups can catch a show at the Chicago Shakespeare Theater, flex some credit card muscle at a variety of shops or grab a drink at the Navy Pier Beer Garden. And be sure to check Navy Pier's website for a list of events: Concerts are often held here, and from Memorial Day to Labor Day (as well as New Year's Eve), impressive fireworks displays light up the skies on Wednesday and Saturday nights. Many of the city's top Segway tours offer special summer evening tours to the pier to catch the semiweekly fireworks show.

Skydeck Chicago at the Willis Tower Skydeck Chicago at the Willis Tower

More than 1.7 million people make their way to Willis Tower's Skydeck Chicago each year, and it's easy to see why. Occupying the 103rd floor – that's nine floors higher than 360 CHICAGO – of the 110-story Willis Tower (the third-tallest building in North America after One World Trade Center and Central Park Tower), Skydeck Chicago boasts breathtaking views of the city. Visit on a sunny day and you may be able to see far beyond Chicago's borders to Indiana, Michigan, Wisconsin and other parts of Illinois.

The highlight for most visitors is the Ledge. Extending 4.3 feet beyond the building's exterior, this platform is made entirely of glass – even the floor. Travelers also liked the video screens that show what it would be like to stand 103 floors above other Chicago attractions, including Wrigley Field and Millennium Park . However, long lines quickly form for Skydeck Chicago, so plan on arriving early or purchasing a Chicago CityPASS, which covers expedited admission into the attraction. Or, simply pay extra for expedited entry, which features an express line to the elevators. For the best views, it's advised that you visit just after opening or after sunset. If you'd like to enjoy the sunset from the tower, plan on arriving 30 to 45 minutes before sunset to ensure you have enough time to get through the elevator line and up to the top.

The Chicago Theatre The Chicago Theatre

Aside from Cloud Gate and Buckingham Fountain , The Chicago Theatre's red and yellow marquee is perhaps one of the city's most recognizable landmarks. Illuminating North State Street at the northern edge of the Loop, The Chicago Theatre first opened its doors in 1921 as an extravagant movie theater and performance venue. Throughout its history, the theater has hosted such big names as Duke Ellington, Diana Ross and Prince, in addition to screening blockbuster flicks. Though the theater fell into disuse in the 1970s, new management and a full renovation in the 1980s helped return the venue to its former glory. Today, the theater is still used for a variety of comedic, theatrical and musical performances.

According to past patrons, the theater's historic appearance enhances the overall experience of catching an event here. Just remember, cameras and video cameras, including those on cell phones, cannot be used during tours or performances. If you're not in town for a show, consider signing up for one of the venue's guided tours. Tour tickets cost $20 for adults and $15 for kids ages 12 and younger. Tours are available Monday and Tuesday at noon and 2 p.m. and last about an hour.

Lincoln Park Zoo Lincoln Park Zoo free

U.S. News Insider Tip: North Avenue Beach is a short walk over the North Avenue Bridge when you park at the southern end of the Lincoln Park Zoo lot. Explore the zoo, then stroll over to the beach for an afternoon in the sand. – Cortney Fries

Located 2 miles north of the Loop in the North Side neighborhood of Lincoln Park, the Lincoln Park Zoo is home to nearly 200 species, such as zebras, sloths and hippos. Visitors can view the zoo's furry (or scaly) friends in their natural habitats: Check out the gorillas in the sprawling, award-winning Regenstein Center for African Apes, or head to the Kovler Seal Pool to get up close and personal with harbor seals. Seal training and feeding occurs daily at 11:30 a.m. and 2 p.m.

Wrigley Field Wrigley Field

U.S. News Insider Tip: If you're visiting during the holiday season, don't miss Winterland at Gallagher Way for family-friendly rides and games inside and around the ballpark. Christkindlmarket Wrigleyville is free to enter. Enjoy festive shopping and international food and beverage selections. – Cortney Fries

Chicagoans take their love of sports very seriously. So, for a real taste of Chicago culture, head north of the Loop to Wrigley Field to watch the Chicago Cubs play ball at the Friendly Confines. History buffs will also appreciate this sports treasure, which first opened in 1914 and holds the honor of being the second-oldest Major League Baseball stadium in the country (after Fenway Park in Boston ).

Popular Tours

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• 3 Days in Chicago: The Perfect Itinerary for First-Timers

Looking to spend 3 days in Chicago but don ’t know where to start? Well, this guide is here to help you out!

Chicago is one of the most populated cities in the United States and sits on the shores of Lake Michigan. Known as ‘the Windy City’, Chicago attracts millions of visitors each year and it’s no surprise why.

With its iconic attractions, towering skyscrapers, and scenic views, this city has made it onto many people’s bucket lists. 

But how should you spend your 3 days in Chicago? This guide will go through the must-visit sites, how to get around the city, and the best places to stay. 

Without further ado, here is the ultimate 3-day Chicago itinerary!

* Disclosure: This post contains a few affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through my link. *

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Table of Contents

Useful Info for Spending 3 Days in Chicago

How to get to chicago.

Chicago O’hare International Airport is the city’s primary airport and is located just 16 miles (26 km) from Downtown Chicago. However, you’ve also got Chicago Midway International airport too. 

Flying is one of the most popular ways to reach Chicago as between them, both airports offer inbound and outbound flights to over 240 destinations across the world. You’ll also find plenty of great deals on domestic flights within the United States too.

If you’re wanting to save some money you can catch a bus or train to Chicago from other major cities in the U.S. 

The most popular coach routes are from New York, Buffalo, Dallas, Minneapolis, and Detroit. However, Greyhound also runs 20 express routes to and from major cities and has five locations within the city.

Catching a train is another popular choice, and the best option is Amtrak . They offer routes to over 500 destinations within the United States and Canada, so you’ll easily be able to reach the city. 

Many of the coach and bus trips to Chicago often run overnight if you’re traveling a long way, which will also help you save on accommodation costs. 

Best time to visit Chicago

Chicago’s high season runs from June to August, and temperatures range from 61°F (16°C) to 85°F (29°C) during this time. 

You’ll also find plenty of festivals and sports games to attend in the summer months, but be prepared to pay top prices for accommodation. 

If you’d prefer a quieter and cheaper experience, then visiting Chicago during the shoulder season is a great option.

The city’s shoulder season falls between April-May and September-October, and you’ll also find the tourist attractions to be much less crowded. 

Between April and May, temperatures range from 39°F (4°C) to 71°F (22°C) while during September and October, the temperature fluctuates between 45°F (7°C) to 76°F (24°C).

Although the weather is cooler and you’re likely to see more rain, you can get great bargains on accommodation and transport.

How to get around in Chicago

Chicago is super easy to get around as public transport is efficient and runs regularly. 

The best way to explore the city is by using the ‘L’ Train. There are 8 colored network lines that will take you to most of the areas and attractions in Chicago. Two of these run 24 hours a day, while the others typically operate between 4 am to 1 am. 

You can purchase single standard passes, but it’s cheaper to purchase a one-day or three-day pass depending on your itinerary. 

Buses are also a great way to get around as 129 routes run throughout the city. Some of these bus routes run on a 24-hour basis, while others operate until 11 pm or  2 am. 

If you’re looking to head out into the suburbs then you can take the Metra Rail. 

Taxis can also be found throughout the city but they aren’t cheap, although Uber and Lyft are available here. 

However, one of the coolest ways to get around the city is by water taxi. They offer a fast and affordable way to travel along the Chicago River, Lake Michigan, and between tourist attractions. 

They do only run between May and September/October though so you’ll need to keep this in mind. 

Although you can hire a car and drive around the city center, I wouldn’t recommend it – especially if you only have 3 days in Chicago. The traffic is a nightmare and parking is extremely limited (and very pricy).

Where to stay in Chicago

There are endless neighborhoods within the city so deciding where to stay in Chicago isn’t an easy decision. So, here is a quick guide to the main areas of the city: 

• Downtown Chicago/The Loop  – perfect for first-time visitors
• River North – the best place to stay for nightlife
• Wicker Park – one of the coolest areas in Chicago
• The Gold Coast – a beautiful area along Lake Michigan
• Magnificent Mile – known for luxury stays and shopping

There are plenty of great areas to stay within the city, but these are just a few of the most popular ones. If you’re interested in knowing more about each neighborhood, make sure to read my detailed guide about the best areas to stay in Chicago .

If you ’re in a rush, here are my top recommendations for different budgets.

LUXURY – Viceroy Chicago

Viceroy Chicago is situated in the scenic Gold Coast area and is just minutes away from the Magnificent Mile and Lake Michigan. This hotel has all the facilities you could need for a luxury stay including a rooftop bar and lounge, a fitness center, on-site dining, and a seasonal rooftop pool.

MID-RANGE – Hotel EMC2

Hotel EMC2 is located in Streeterville and is right by the Magnificent Mile and Downtown Chicago. Millennium Park and Navy Pier are also just 1 mile (1.6 km) away. Not only are the rooms beautiful and spacious, but this hotel also has on-site dining available, a fitness center, and a dry-cleaning service. 

BUDGET – Central Loop Hotel

All guest rooms at Central Loop Hotel have custom-designed furnishings and comfortable beds with down duvets and plush pillow-top mattresses. They also include work desks with ergonomic chairs. Complimentary exercise equipment and air purifiers are available for room delivery upon request.

Overview of Your 3 Day Chicago Itinerary

Breakdown of your 3 days in chicago.

• Day 1: Breakfast at ​​Goddess and the Baker, Millennium Park (Cloud Gate, Crown Fountain, Lurie Garden), The Art Institute of Chicago, Navy Pier, Dinner at Giordano’s, Sunset at Milton Lee Olive Park
• Day 2: Breakfast either at Beatrix or Wildberry Pancakes & Cafe, Starbucks Reserve Roastery, Magnificent Mile, Chicago Riverwalk, Chicago Theatre, Chicago River Architecture Cruise, Nature Boardwalk at Lincoln Park Zoo, Sunset at North Avenue Beach, Dinner at Portillo’s Hot Dogs
• Day 3: SkyDeck Chicago, Breakfast at Mojo Coffee, Grant Park & Buckingham Fountain, Museum Campus (Shedd Aquarium, Field Museum, Adler Planetarium, Soldier Field), Dinner at Lou Malnati’s Pizzeria

Map for your 3 day Chicago itinerary

Below you can find a customized map that includes all the locations you’re going to visit on this Chicago itinerary.

I marked your 3 days in Chicago with different colors – I used blue for the first, yellow for the second, and green for the third day, so you can easily see which places you’re going to visit each day.

If you open up this post on your phone and you click on the bracket in the upper right corner of the map, it will open up in your Google Maps app so you can always have it with you. Super convenient, right?

Day 1 of Your 3 Days in Chicago

Breakfast at ​​goddess and the baker .

Grabbing a bite to eat at the Goddess and the Baker is the perfect way to fuel your day of exploring. It’s famous for its great food, amazing coffee, and fun treats!

They have a wide selection of breakfast options including yogurt parfait, omelets, bagels, and waffles so you won’t have a problem finding something to your taste here.

There are multiple locations of Goddess and the Baker, but this one is right across from Millenium Park (the next stop on your 3 day Chicago itinerary). You can either have breakfast first thing in the morning or after you’ve visited the park – it’s completely up to you! 

Millennium Park and The Bean

After (or before) breakfast, make your way to Millennium Park which is one of the most famous landmarks in Chicago. 

Spanning over 24.5 acres, this park is home to many popular attractions including the Cloud Gate (aka ‘The Bean’).

The Cloud Gate is a public sculpture that was designed by British artist Anish Kapoor. It’s made up of 168 stainless steel plates and weighs in at a whopping 110 tons!

You can walk around the sculpture, take photos, and even go underneath it. Thanks to its reflective surface, it has quickly become one of the most Instagrammable places in Chicago . So be prepared for the crowds as this is one of the most popular things to do in Chicago!

After you’ve had your fill of The Bean, continue exploring Millennium Park. There’s plenty to see and do here including visiting the Lurie Garden, which is a 2.5-acre public garden, or checking out the Crown Fountain which is a work of art in itself!

The Art Institute of Chicago

The Art Institute of Chicago is another popular attraction as it’s one of the world’s largest (and oldest) art museums. 

Aside from its ever-changing exhibitions, the museum has a permanent collection of around 300,000 art pieces which is pretty impressive. 

These ongoing exhibitions include the ‘Of Gods and Glamor’ exhibit, ‘a New View of African Art’, and the ‘Landscape in Light’ exhibit. 

The museum attracts around 1.5 million people annually and is a must-visit on your 3 day trip to Chicago. 

It’s important to note that the Art Institute of Chicago is closed on Tuesdays and Wednesdays, so you’ll have to time your visit right if you want to visit this spot.

Otherwise, it ’s open between 11 am – 5 pm from Thursday to Monday and general admission costs $25 per person.

TOP TIP: In case you want to visit multiple attractions, take a look at the Chicago CityPASS which can help you save 48% or more on the top attractions. It includes access to The Art Institute of Chicago, Shedd Aquarium and SkyDeck Chicago among many other popular sites.

Next up on your 3 days in Chicago itinerary is a visit to Navy Pier, a 3,300-foot-long pier that sits on the shores of Lake Michigan.

It’s one of the most popular tourist destinations in the city and it’s easy to see why with its many attractions, shops, and restaurants.

You’ll find plenty to do here including fairground rides, live music performances, theater productions, and special events. Not to mention the incredible views to be had from the pier itself!

One of the unmissable things to do in Navy Pier is going on a ride on the Centennial Wheel, which is a 200-foot tall Ferris wheel. From the top, you’ll be able to see amazing views of the cityscape and beyond! Since it’s a fairly popular attraction, it’s best to purchase your tickets in advance .

If you’re looking to do some shopping, Navy Pier is also home to a variety of stores selling everything from souvenirs to clothing.

Dinner at Giordano’s 

And when you’re ready to refuel, there are plenty of restaurants and cafes in Navy Pier to choose from including the food court which has options to suit all tastes.

My personal recommendation for today ’s dinner is Giordano ’s . They have multiple locations throughout the city but this one is actually at Navy Pier so you won’t have to wander far. 

Giordano ’s is home to the best deep dish pizzas in all of Chicago, and you’ll find plenty of tasty topping options here.

Some of the most popular choices include ‘meat and more meat’, the ‘Chicago classic’, and the ‘super veggie’. You can even make your own if you fancy!

In case you’re not in the mood for pizza, they also have a delicious range of pasta dishes and sandwiches. If you’re looking to see (and taste) the best of Chicago in 3 days, this is the restaurant you need to visit!

Sunset at Milton Lee Olive Park

Watching the sunset at Milton Lee Olive Park is the perfect way to end the first day of your 3 days in Chicago. 

The park is named after Milton Lee Olive who was given a medal of honor for his actions in the Vietnam War. 

It’s located on a man-made peninsula that juts out onto Lake Michigan, so naturally, it boasts spectacular views – especially at sunset. You’ll also find plenty of walks here that offer superb views of the Chicago skyline.

However, the highlight of Milton Lee Olive Park has to be the fountains! There are five circular fountains in total and each one is connected by walking trails. 

Day 2 of Your 3 Days in Chicago

Breakfast either at beatrix or wildberry pancakes & cafe .

Breakfast is the most important meal of the day, and these two places are incredible! 

Both Beatrix and the Wildberry Pancakes & Cafe have multiple locations throughout the city and you’ll find one relatively close to the Magnificent Mile (the next attraction on your 3 day Chicago itinerary).

Wildberry Pancakes & Cafe is one of the best choices when it comes to breakfast places in Chicago. As the name suggests, pancakes are their specialty and you’ll be spoiled for choice with all of the different flavors on offer.

There are also plenty of other breakfast options available including eggs, bacon, sausage, bagels, and more. Their French toasts are also incredible!

If pancakes aren’t your thing, another great option for breakfast is Beatrix . This restaurant has a focus on healthy and flavorful food with plenty of vegan and vegetarian options available.

You’ll find everything from avocado toast to quinoa bowls on the menu, as well as a selection of fresh juices and smoothies.

Starbucks Reserve Roastery

After breakfast, make your way to the Starbucks Reserve Roastery . This is a must-visit for any coffee lover!

Starbucks Reserve Roastery is home to a selection of the rarest and most extraordinary coffees on earth. Not only that, but it’s the largest Starbucks in the world with five floors covering over 35,000 sq ft. 

Usually, you’d head to a Starbucks for a quick coffee but not here! The Starbucks Reserve Roastery offers interactive tours, a rooftop deck to admire the city views, and delicious pastries. 

Trust me, if you’re into coffee then you don’t want to miss out on this place during your 3 day trip to Chicago.

Magnificent Mile

The Magnificent Mile is without a doubt one of the most popular places to visit in Chicago. It’s one of the most famous shopping destinations in the world and is home to huge shopping centers, boutique stores, and plenty of designer shops. 

However, there is so much more to do here than just shop! Some of the most popular attractions include the John Hancock Center, the Wrigley Building, and the Tribune Tower. You can also head to the free gallery within the Water Tower.

If you’re looking to do some shopping, you’ll find everything from high-end stores to budget-friendly options. And when you need a break from shopping, there are plenty of restaurants and cafes to choose from.

Chicago Riverwalk

After exploring the Magnificent Mile, make your way to the Chicago Riverwalk. This is a great spot to relax and take in the views of the city.

The Chicago Riverwalk is a 1.25 mile (2 km) path that is made up of four districts; the Arcade, the Civic, the Confluence, and the Esplanade. 

The path starts from Lake Street and runs along the Chicago River until it reaches Lake Michigan. 

Along the way, you’ll get to see a variety of public art including banners, murals, and sculptures so make sure you take your time walking this path. 

However, the highlights of the Chicago Riverwalk have to be the iconic Wrigley Building and the DuSable Bridge. With so much to offer, this riverwalk needs to be on your 3 days in Chicago itinerary! 

Chicago Theatre

The Chicago Theatre was constructed in 1921 and designed by Cornelius Ward Rapp and George L. Rapp. It was the first lavish movie palace in the United States and was incredibly successful. 

This led to the owners (Balaban & Watz) constructing other theaters of its design throughout America. 

The whole design of the theater is based on luxury, which is clear just by taking a look at the grand lobby inside.

During your stay in the city, I’d recommend catching a show here to fully experience this incredible building. You can take your pick from comedy shows, live music performances, and theater productions.

However, if you don’t have time then simply head inside and go on a tour – trust me you won’t regret it!

Chicago River Architecture Cruise 

If you’ve only got 3 days in Chicago, then going on a river cruise has to be at the top of your list. Chicago River architecture cruises usually last around 1.5 hours and typically start at DuSable Bridge. 

One of the best choices is this river cruise that will take you down the Chicago River and past some of the city’s most iconic buildings.

You’ll also learn all about the history and architecture of each building from your knowledgeable tour guide. Best of all, it allows you to skip the ticket office and board straight away!

Alternatively, this 1.5-hour river cruise is a great option as well.

If you’re a bit short on time or want to keep the children entertained, then this family-friendly river cruise is a great choice. It’s only 45 minutes long but will still show you the city’s most breathtaking landmarks.

Nature Boardwalk at Lincoln Park Zoo 

After your architecture cruise, make your way to the Nature Boardwalk at Lincoln Park Zoo. This is a great spot to unwind and take a break from all the hustle and bustle of the city.

The Nature Boardwalk is an oasis within the city with plenty of trees, flowers, and greenery. There’s also a pond where you can spot turtles, ducks, and other wildlife.

One of the unmissable sights within the Nature Boardwalk is the Educational Pavilion which is one of the most unique things you’ll see during this 3 day Chicago itinerary.

The honeycombed shaped pavilion is constructed of prefabricated wood elements and the arched structure forms a place to shelter during your exploration of the park.

If you have some extra time on your hands, I also recommend checking out the Lincoln Park Zoo. It’s one of the oldest zoos in the country and it’s completely free to visit!

Sunset at North Avenue Beach

There’s no better way to appreciate a new city than by admiring an epic sunset. Chicago has plenty of incredible opportunities for this but watching the sunset at North Avenue Beach just hits differently! 

It’s one of the city’s most popular beaches and is located within Lincoln Park so you won’t have to walk far after visiting the Zoo or the Nature Boardwalk. 

Not only is North Avenue Beach beautiful, but you’ll also find an awesome beach house here too. The building is inspired by an ocean liner and offers a top deck where you’ll get spectacular views – especially at sunset. 

Make sure to stay a bit longer after the sunset to see the city all lit up. It ’s truly an incredible experience!

Dinner at Portillo ’s Hot Dogs

Chicago has endless options for dining, but you definitely need to try Portillo’s Hot Dogs during your 3 days in Chicago.

This Chicago born-chain is famous for its juicy hot dogs, tasty burgers, and delicious chocolate cake. Their Italian beef sandwiches are also a big hit. They even have vegan hot dogs so they cater to every dietary requirement. 

After a long day of exploring, eating at Portillo’s Hot Dogs is the best (and tastiest) way to refuel. 

Day 3 of Your 3 Days in Chicago

Skydeck chicago.

To truly make the most out of your 3 days in Chicago, you’ll want to head up to Skydeck Chicago during your visit. Located on the 103rd floor in the Willis Tower, Skydeck Chicago offers breathtaking views of the city.

If you head up there on a clear day you’re really in for a treat, as you’ll be able to see up to 50 miles (80 km) away including four American states! 

Are you feeling daring? If so, you should head out onto the ledge. The ledge is made up of four glass view boxes, and you’ll get a completely unobstructed view of Chicago. However, this probably isn’t suitable for people with a fear of heights, as it’s pretty daunting!

Since it ’s one of the most popular attractions in Chicago, I recommend heading there first thing in the morning right when it opens (usually around 8.30 am – 9 am). It ’s also advisable to book your tickets in advance so you don ’t lose any time waiting in the line.

Breakfast at Mojo Coffee

Mojo Coffee is a great place to fuel yourself for the last day of this 3 day Chicago itinerary.

You’ll find plenty of locations throughout the city but I’d recommend heading to this one as it ’s located right next to the Willis Tower. Plus, it ’s the very first cafe they ’ve opened in Chicago after their success in New Zealand!

Mojo Cafe offers plenty of tasty food options, including waffles, shakshuka, salads, poached eggs, and avocado on toast for starters.

They also have a delicious range of smoothies including ‘cold brew & chocolate’ and ‘pear, pineapple & spirulina’.

Also, if you ’re a coffee lover, grabbing a cup here is mandatory – and you can also take some freshly roasted coffee beans home with you.

Grant Park & Buckingham Fountain

After you’ve had your fill of the views from Skydeck Chicago and you ’re stomach is full, make your way to Grant Park. This is one of the most popular spots in the city and it’s easy to see why.

The park is huge (319 acres to be exact!) and there’s so much to see and do here. From gardens and sculptures to museums and fountains, there’s something for everyone in Grant Park.

One of the most popular attractions in the park is Buckingham Fountain. This iconic fountain is one of the largest in the world and uses around 15,000 gallons of water per minute.

The fountain also performs a water show hourly so make sure you time your visit right to witness it. You can also decide to come back after nightfall when you can enjoy a light and music display with the water show.

Museum Campus 

After you’ve explored Grant Park, make your way to Museum Campus. This 57-acre park is home to some of the best museums in the city including the Field Museum, the Shedd Aquarium, and the Adler Planetarium.

If you’re visiting with kids, they’ll definitely want to check out the Field Museum . This world-renowned museum is home to Sue, the largest and most complete Tyrannosaurus Rex fossil ever found.

Adults will appreciate the Shedd Aquarium which is one of the largest indoor aquariums in the world. And if you’re interested in space, the Adler Planetarium is a must-visit.

Visiting all 3 museums is pretty time consuming so I would recommend choosing one or two that take your fancy, so you can take your time and not rush around. No matter which museum you choose to visit, you’re sure to have a great time at Museum Campus!

TOP TIP: To make the most out of your visit and to save some cash, I’d recommend getting the Chicago CityPASS . It allows you to visit five of the city’s top attractions (including all 3 museums in Museum Campus) and you can save up to 48% off the normal ticket prices.

Dinner at Lou Malnati’s Pizzeria 

After a day of exploring, you’re going to want a delicious dinner. And there’s no better place for that than Lou Malnati’s Pizzeria .

This iconic pizzeria has been serving up delicious deep dish pies since 1971 and is hands-down the best place to get pizza in the city. They use an exclusive sausage blend, vine-ripened plum tomatoes, and Wisconsin cheese to make the most delicious toppings. 

You can either create your own pizza here, or you can try one of their many tasty options including the ‘Malnati Chicago Classic’, ‘The Lou’, and the iconic pepperoni. 

Lou Malnati’s Pizzeria also has a wide variety of pasta dishes, salads, sandwiches, and desserts.

They have multiple locations throughout the city, this one is the closest to Millenium Park. There is no better way to end your 3 days in Chicago, than by dining here!

Planning a trip to Chicago?

Then you might want to take a look at all our other travel guides about Chicago. I promise, they are just as awesome as this article was!

• Top 8 Best Areas to Stay in Chicago
• 22 Amazing Hotels with the Best Views in Chicago
• 13 Stunning Chicago Hotels with Lake Views
• 15 Most Instagrammable Places in Chicago You Can’t Miss
• 107 Incredible Chicago Captions for Instagram

Read about more US States: California | Massachusetts | Maine | Nevada | New Hampshire | New York | Vermont

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One-Day Itinerary

One Day in Chicago: The Perfect Itinerary

TripSavvy / Cory Giguere 

Don’t let the winds blowing off Lake Michigan scare you— Chicago , the Windy City, is a metropolis full of culture and history. Sightseers flock to the birthplace of the skyscraper, for its: Michelin-starred restaurants ; major league sports teams; world-class theater, dance, music, and film; festivals; 26 miles of lakefront; well-curated museums ; and stellar shopping. Chicago is also full of green spaces that are worth exploring like Chicago Botanic Garden and The Morton Arboretum . No matter what you do, or where you go, you’ll appreciate the city’s midwestern allure, with a bit of urban edginess. 

This walking-city, with 2.7 million residents, utilizes speedy public transportation to get from point A to point B. As you get on and off the elevated rail, or L, you’ll notice a mashup of sleek and modern buildings with loads of history and nods to the past throughout Chicago’s 46 historic districts and 77 vibrant neighborhoods. Chicago River architecture tours or walking excursions will highlight the City of the Big Shoulders’ storied past—the rise of a transportation hub, the Great Chicago Fire, the World’s Columbian Exposition of 1893, prohibition era, and Chicago’s public enemy number one, Al Capone .

Whether you’re a first-time visitor to the Second City, or a seasoned local, peruse this 24-hour itinerary for an across-the-board exploration of what Chicago has to offer, highlighting must-see tourist spots as well as local neighborhood gems.

The Night Before

Night: Arrive in Chicago and check-in to your accommodations—there are 119 hotels to choose from in the central business district. Luxurious options in the city include: Waldorf Astoria Chicago , Four Seasons Hotel Chicago (the spa here is fantastic), The Langham Chicago , Park Hyatt Hotel Chicago , and The Peninsula Chicago (the lobby is exquisite). Other well-located alternatives are Hotel Zachary , near Wrigley Field (the second oldest ballpark in Major League Baseball); Hotel EMC2 , with a robot concierge; and InterContinental Chicago Magnificent Mile , with a hidden hole in the wall for a prohibition-era alcohol stash.

Intrepid families that would love to spend a night at one of the museums can bring a sleeping bag and a sense of adventure to Adler Planetarium’s Astro Overnights, the Field Museum’s Dozin’ with the Dinos, Overnights at the Shedd Aquarium , or the Museum of Science and Industry’s Science Snoozeum.

7:30 a.m.: Take advantage of waking up in one of the best cities in the world and go for a leisurely jog or a fast-paced walk along the Chicago Riverwalk, a 1.25-mile stretch that has Adirondack chairs toward the east end for catching your breath. You’ll pass by stunning architecture, art installations, and boats cruising up and down the Chicago River. Continue on to the paved Chicago Lakefront Trail, along Lake Michigan, which runs from Ardmore Street on the north side to 71st Street on the south side, traversing many historic neighborhoods like Lincoln Park, South Loop, Bronzeville, and Hyde Park. The skyline views, when you’re facing south, are incredible, especially at this time of day. You can see Navy Pier , Chicago’s most-visited attraction, from the trail, with its Centennial Wheel rising high in the sky. For great people watching, linger at Oak Street Beach for a beat. (The 606, in Logan Square, is another great place to run that is popular with locals. This neighborhood park was created on the old elevated Bloomingdale train line—similar to New York’s High Line .)

10 a.m.: Make your way to Cindy’s for brunch, located on the rooftop of the famed Chicago Athletic Association Hotel , formerly a men-only social club. You won’t believe the terrace view of Millennium Park, The Art Institute of Chicago (the “Historic Route 66” begins in front of the Art Institute), Lake Michigan, and the shops and restaurants below at street level. Make reservations well in advance—this place is always packed—and order the avocado toast and the roasted vegetable strata. Save room for the house-made vanilla mascarpone Danish, with roasted cherries.

Noon: Across from Cindy’s is the 24.5-acre Millennium Park , a well-loved public space that is home to the Jay Pritzker Pavilion, Cloud Gate—the Instagram-worthy shiny bean-shaped sculpture, Crown Fountain, and Lurie Garden. Millennium Park Campus is also where you’ll find Maggie Daley Park, the best place to go if you have kids in tow.

1:00 p.m.: Meet up with Chicago Architecture Foundation ’s guide to learn about Chicago architecture and history on a two-hour walking tour through the city. You’ll get the lay of the land and learn more than you dreamed possible to enrich your time spent in the city. On the way, caffeinate with a cold brew or bulletproof coffee at Goddess and the Baker , located at Wacker Drive and Lasalle Street.

3:00 p.m.: You can’t leave Chicago without weighing in on which pizzeria serves up the best slice of deep dish . Is it Giordano’s, Lou Malnati’s, Pizzeria Due, Gino’s East, Piece, or Home Run Inn? You decide.

5:00 p.m.: Walk off that heavy pizza and stroll along the Magnificent Mile , a 14-block stretch of Michigan Avenue—from the Chicago River to Oak Street—that is mecca for shopping. Here, you’ll find malls and boutiques full of designer threads as well as affordable clothing brands. Keep in mind, this area is usually congested with shoppers, especially around the holidays and on weekends, so it’s best to plan out which shops you’d like to see in advance. Take a few snaps in front of the famous Chicago Water Tower , built in 1869, on the north end of Michigan Avenue. If shopping isn’t your thing, why not take an Intro to Climbing class at Chicago’s Brooklyn Boulders , located in Greek Town, west of the river, near Ogilvie Transportation Center?

6:00 p.m.: Take the high-speed elevator up to the observatory at 360 Chicago (formerly The Hancock Observatory) where, on a clear day, you can see Michigan, Indiana, and Wisconsin. Test your fear of heights on the Skydeck open-air viewing deck and see Michigan Avenue, 1,000-feet below, in the TILT attraction.

7:00 p.m.: You’ll want to experience Chicago’s diverse theater, music, or dance scene—the city has more than 250 theaters, 225 music venues, and 200 dance companies. Long-standing theaters include: The Second City in Old Town, Goodman Theatre and Chicago Theatre in the Loop, Music Box Theatre in Lakeview, Blue Man Group at Briar Street Theatre in Boystown, Steppenwolf Theatre Company , Chicago Shakespeare Theater , Lookingglass Theatre Company , just to name a few. And, of course, Chicago has no shortage of great live music, especially blues and jazz music (the term “jazz” was coined in Chicago). Music festivals like Chicago Blues Festival, Chicago Jazz Festival , Lollapalooza , Pitchfork Music Festival and Riot Fest are well-attended and loved in this city. Not to be missed is Chicago Symphony Orchestra , Lyric Opera and the Joffrey Ballet . The Harris Theater for Music and Dance is home to major Chicago dance troupes. You can’t do it all of course, so pick wisely and plan on returning to Chicago for another go-round in the future.

10:00 p.m.: For late-night noshes, local beers, and inventive cocktails, pop over to Lincoln Park’s Broken Barrel Bar , with Chef Bryant Anderson at the helm. This place is great for that non-touristy neighborhood feel that Chicago is really known for and you’ll get a sense of what one Chicago community is like by playing a game of bags or hanging around in the beer garden. Other great options, with completely different environments are: The Berkshire Room in River North, Milk Room in the Loop, The Aviary in the West Loop , The Violet Hour in Wicker Park, River Roast on the Chicago River, and The Optima in Old Town.

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3 Days in Chicago: Best Itinerary For A Trip To Chicago

Welcome to JetSetting Fools, here you will find our best travel tips for destinations worldwide. Some of the links on this site are Affiliate Links and if you use them to make a purchase, we may earn a commission. For more information, read our Disclosure Policy .

Looking to plan the best trip to Chicago, Illinois? Don’t stress – we have it covered! After visiting the Windy City on numerous occasions, we have created the Ultimate 3 Days in Chicago Itinerary. Including the best sights, must-do activities and local eats, our Chicago trip planner is all you need for a fantastic visit to Chi-town!

How To Plan A Trip to Chicago, Illinois

Planning a Chicago trip can feel overwhelming, but we are here to help! Chicago is steeped in riveting history, decorated with dazzling architecture and is famous for its food scene. While Chicago is bordered on the east by Lake Michigan, the city sprawls in all other directions.

Many of the top Chicago attractions are found in the very walkable downtown loop, and a few must-see Chicago sights are scattered further afield. We are sharing our top tips in a day-by-day Chicago 3-Day Itinerary so that you can plan a Chicago trip without worry.

Pro Tip:  Get (and stay) organized for your vacation to Chicago using our Trip Planning Printables !

3 Days in Chicago

Chicago is one of the best weekend destinations in the United States ! Visiting Chicago in 3 days is just enough time to see the highlights and get a taste of the city – and we squeeze just about all that we can into our perfect Chicago 3 Day Itinerary.

In fact, our trip plan is designed for a long weekend in Chicago – based on the assumption that visitors will arrive on Friday or Saturday and stay until Sunday or Monday. That said, our Chicago in 3 Days Itinerary can be used for trips on any days of the week (with just a few minor adjustments).

While we think three days in Chicago is a perfect amount of time for a visit, we know not all travelers are planning a 3-day Chicago trip. Therefore, we offer alternate Chicago itineraries – for shorter and longer trips – at the end of this article. Whether you are planning a 2-Day Chicago Itinerary, making plans for 4 days in Chicago or devising a Chicago 5-Day Itinerary trip plan, you can use our suggestions for your vacation!

What To Eat & Drink during your Chicago 3 Day Itinerary

Eating is one of the top things to do in Chicago in 3 days. The city is home to numerous legendary eateries – far too many to fit into one fun weekend trip in Chicago. To help, we have narrowed it down to the best Chicago food options.

Throughout our Chicago Three Day Itinerary, we highlight the most famous Chicago restaurants. Our food recommendations include classic eateries, Chicago’s best hot dogs, and – of course – iconic Chicago deep-dish pizza. For drinks in the Windy City, we feature locally brewed beer, swanky cocktail lounges and famous jazz bars. 

You will find all of our recommendations for food and drink sprinkled throughout our 3 Days in Chicago Itinerary.

Our Chicago Itinerary for 3 Days

Our 3-Day Itinerary for Chicago features the best of the city in an easy to follow day-by-day plan. At the end of the post, you will also find our tips for how to get there, where to stay and what to pack.

Our Chicago three-day itinerary includes everything you need to plan your ultimate trip to the Windy City. Save, Bookmark or Pin this post for your Chicago trip!

Day 1 of Your 3 Day Chicago Itinerary: City View, Park, Beach and West Loop

On the first day of your 3-day trip to Chicago, get settled into your accommodations (recommendations below) – then get an overview of the area. Next, explore the city’s best park and beach before setting off for a fun night in Chicago’s West Loop.

360 Chicago Observation Deck

Start your Weekend in Chicago Itinerary with the city’s best view! Zip to the top of 875 North Michigan Avenue – formerly the John Hancock Center  – to the 360 Observation Deck. The elevator ride only takes 40 seconds to travel 1,000 feet – so you should have no problem fitting the activity into your Chicago, Illinois trip plan!

Inside the 360 Observation Deck, visitors are greeted with incredible views of the Chicago skyline and Lake Michigan. Spend some time leisurely soaking in the view, sipping a drink at the bar or experiencing TILT – which claims to be the Highest Thrill Ride on the Planet. Buy your tickets now!

Historic Chicago Water Tower, Lincoln Park and North Avenue Beach

With your feet back on the ground, see some of the highlights of the City of Chicago. Walk to a historic landmark, through a beautiful park and along the shoreline on a Chicago beach.

The Chicago Water Tower still stands as a top Chicago landmark. Built in the 1860s, the tower is located on the famous Magnificent Mile. It is one of the few buildings that survived the 1871 Great Fire of Chicago. Although now in the shadow of skyscrapers, the tower is an important part of history and should not be missed by visitors to Chicago. 

Next up on your 3 Day Chicago Trip is the city’s best green space: Lincoln Park. Explore the myriad of paths that crisscross through the expansive lakeside Lincoln Park. If you are planning a trip to Chicago with kids, consider stopping at the Lincoln Zoo (it’s free!)! If the weather is cooperating, continue your walk on the sand at North Avenue Beach – and if it’s summertime, consider taking a swim in Lake Michigan!

Deep Dish Pizza for Lunch

For lunch, indulge in Chicago’s culinary creation: Deep Dish Pizza. Lou Malnati’s Pizzeria is a Windy City favorite known for their butter crust – and is a must-try during your 3 days in Chicago. The family-owned restaurant has several locations (including one just south of Lincoln Park).

That said, it’s not the only place to get gooey deep dish deliciousness on your weekend Chicago trip. There are dozens of highly acclaimed pizzerias serving up deep dish pies in Chicago. Giordano’s, Pizzeria Uno and Gino’s East are all good options for Chicago deep dish pizza. The Chicago Pizza and Oven Grinder Company, however, gets our vote and many rave reviews for their deep dish pizza and creative Pizza Pot Pies. 

Goose Island Fulton Street Brewery Tour

After lunch, continue to the next stop on your Three Days in Chicago Itinerary: The Chicago-born Goose Island Brewery. Established as a small city brewpub in 1988, Goose Island is now a globally recognized beer brand (thanks in no small part to it’s acquisition by Anheuser-Busch in 2011).

At the Fulton Street Brewery and Taproom, patrons are invited to take a brewery tour to witness the behind-the-scenes production process…and then sip delicious, fresh beer. Even if you skip the tour, this is a fun brewpub and should definitely be included on a beer-lovers three day Chicago Itinerary!

Time Out Market Chicago

We were first introduced to the concept of Time Out Markets in Lisbon, Portugal , where we were absolutely thrilled that they brought the best local chefs under one roof. At the Chicago Time Out Market, which is situated in the heart of the West Loop dining district, the idea is the same – and we think it’s a must for your Chicago Itinerary!

Visitors can order dishes from any of the carefully selected 18 Chicago chefs. The warehouse-style market encompasses 50,000 square feet of dining space – and includes 3 bars and a rooftop terrace.

The buzzing Time Out Market features Chicago classics, international fare and decadent desserts that are all well-recognized brands of the city.

A Night Out during Your 3 Day Itinerary Chicago

While patrons can linger at the Time Out Market bars, with only a weekend in Chicago, we recommend moving on to one of the hip bars in the West Loop (or beyond).

Best Bars for Day 1 of your 3 Days in Chicago

There is no shortage of hangouts in West Loop, so where you go depends on your taste. To help you decide, we’ve rounded up a short list of some of the fun bars you can add to Day 1 of your Chicago 3 Day Itinerary.

Blind Barber

Just a block west of the Time Out Market is Blind Barber, a barbershop by day…and a swank, 70s-style speakeasy by night.

Emporium Fulton Market

The fun Emporium Fulton Market is just down the street to the east – and features an array of arcade games and craft cocktails.

Lone Wolf Chicago

A favorite local neighborhood spot, the Lone Wolf is a classic and comfortable establishment to add to your Chicago night out.

Haymarket Brewery

If you are in search of Chicago craft beer, don’t miss Haymarket Pub and Brewery. They also feature live music on weekends.

Green Mill Cocktail Lounge

However, visitors who are planning a trip to Chicago and want to sip a cocktail inside a Chicago institution should leave the West Loop and head uptown to Green Mill Cocktail Lounge.

The iconic bar opened in 1907, was partly owned by Al Capone during Prohibition, has hosted famous singers – such as Billie Holiday – and now regularly features jazz and poetry nights. Just be prepared; it’s a bit north of the city, there is a cover charge, it’s cash only and seating is first come, first served.

Day 2 of Your Chicago Itinerary in 3 Days: The Loop, Architecture and Windy City Sports

On the second day of your Chicago in a Weekend Itinerary, explore top attractions on foot and by boat, then end the day in a classic northside neighborhood, maybe even watching a baseball game!

Breakfast At The Famous Lou Mitchell’s

For breakfast on Day 2 of your Chicago trip, indulge in a hearty Midwest-style meal at the iconic Lou Mitchell’s. For a 100 years, the diner has been serving up omelets and pouring coffee for hungry patrons. Definitely old school and a little quirky (they hand out Milk Duds), eating at Lou Mitchell’s is a Chicago must!

Union Station Chicago

Ease into your full day of Chicago sightseeing at the landmark Union Station. Opened in 1925, the station serves Amtrak and Metra commuter lines – and ranks as the busiest rail station in the United States outside of New York City . Occupying an entire city block, the classic Great Hall waiting room is at the center – and is recognizable from many popular Hollywood films including The Untouchables and My Best Friend’s Wedding.

The Loop Walking Tour

Spend the rest of the morning walking off your Midwest breakfast on a self-guided walking tour of the Chicago downtown Loop. The district features historic architecture, lush parks and intriguing artworks. Exploring this area is an absolute must when visiting Chicago.

Trip Planner Chicago Loop

Begin your discovery at the well-recognized Willis Tower (formerly the Sears Tower), which ranked as the tallest building in the world when it was completed in 1973. Visitors can soar to the 103rd floor Skydeck Chicago (be sure to buy your ticket in advance !). After visiting the Willis Tower, continue on your tour of the Chicago Loop.

Explore the following Chicago Loop sights (in order) and use this link to Google Maps for locations.

• Daley Plaza (and Picasso’s Untitled artwork)
• Miro’s Statue
• Chicago Theater (and famous Chicago sign)
• Old Marshall Field Building (and legendary clocks)
• Chicago Cultural Center (and Tiffany Dome)
• Millennium Park and Grant Park (Cloud Gate mirrored sculpture a.k.a. The Bean , Crown Fountain – then detour out of the park to see the historic Route 66 Begin sign and go one block west to see the famed Palmer House Hilton Hotel – Chicago Stock Exchange Arch, Buckingham Fountain)
• Queen’s Landing
• Lakeshore Trail  
• Chicago Riverwalk (view The Wrigley Building and Tribune Tower across the river)
• DuSable Bridge

Billy Goat Tavern For Lunch 

End the tour by crossing the DuSable bridge and walking north on Michigan Avenue to the Plaza of the Americas – then have lunch at Billy Goat Tavern. This iconic eatery is surely a highlight of any weekend trip to Chicago. 

Established in 1934, the Billy Goat Tavern opened at the Lower Michigan Avenue location in 1964 and has been serving their famous “Cheezborgers” ever since. The original owner was the historic instigator of the Chicago Cubs’ Curse of the Billy Goat and the tavern was the inspiration for the Olympia Café in 1970s Saturday Night Live sketches .

Chicago Architecture River Cruise

After lunch, hop on a boat for a different perspective of the Chicago skyline – it’s an absolute must for a summer Chicago weekend itinerary. Enjoy an entertaining hour-long river cruise along the three branches of the Chicago River. The on-board tour guide shares the history of the city and more than 40 buildings that you will pass along the way. Book your seat now!

Wrigleyville (and a Cubs Game)

Home to the much-loved Chicago Cubs (unless you’re from the South Side or St. Louis), Wrigleyville is a north side neighborhood packed with lively bars and fantastic eateries. The historic Wrigley Field is at the heart of the neighborhood – and attending a baseball game (regardless of who you’re rooting for) is a highlight of any itinerary for Chicago.

If the Cubbies are not playing while you are vacationing in Chicago, it is still worth visiting the neighborhood for dinner and drinks. Visit one of the famous Clark Street sports bars – like the Cubby Bear or Sluggers – for simple grub and drinks (or go for a gastropub dinner at Mordecai).

If the Cubs are away and seeing a baseball game is at the top of your list of things to do in Chicago, then check the South Side White Sox schedule.

Outside of the summer baseball season, there are numerous pro sports events that you could add to your three days in Chicago trip plan. Check schedules for the world famous Chicago Bulls (basketball), Chicago Bears (football), Chicago Blackhawks (ice hockey) and Chicago Fire (soccer).

Day 3 of Your Weekend in Chicago Itinerary: Walking Trail, Hot Dogs & Navy Pier

Wrap up your 3 Days in Chicago Itinerary with more sightseeing, eating and walking it off! Start the day at a cool urban park, embark on a local food tour, get a birds’ eye view of the city and end your Chicago tour itinerary at tourist hotspot, Navy Pier.

Walk Off the Food You’ve Eaten in Chicago in 3 Days

When we plan a trip to Chicago that includes gorging on the local fare, we also carve out time to walk it off. While our Weekend in Chicago Itinerary naturally includes a lot of walking between sights, there are two fabulous places to hit really stretch your legs: 606 Bloomingdale Trail and Lakefront Trail.

The 606 Bloomingdale Trail 

Similar to the New York City Highline and the Paris La Promenade Plantee, the Bloomingdale Trail at The 606  is a repurposed elevated train track-turned-public-park. Running three miles through four districts (Wicker Park, Bucktown, Humbolt Park and Logan Square) on Chicago’s northwest side, the walking trail features art installations and hosts local events.

We recommend walking The 606 from east to west. Churchill Field Park is a great place to hop on the trail. Pop into Mindy’s Bakery, run by famed Chicago chef Mindy Segal, for an incredible breakfast before starting your walk. Just be warned, there will likely be a line out the door – breakfast at Mindy’s is one of the top things to do in Chicago on a weekend – and it’s closed Monday – Wednesday.

Lakefront Trail

As the name suggests, the Lakefront Trail fronts Lake Michigan – and, for many visitors, walking along the shoreline is a highlight of a 3 Day Itinerary for Chicago. The trail stretches for 18 miles and can be used by bicyclists and pedestrians. From the path, there are fabulous views of Chicago and the shoreline. Hop on at any point and walk as far as you would like!

Famed Chicago-Style Hot Dogs

Your Chicago Trip Planner is not complete without consuming at least one hot dog. Chicago Dogs are noted for being ‘dragged through the garden’ – meaning, piled high with toppings that include mustard, onions, relish, tomatoes and a dill pickle spear sprinkled with celery salt (but never ketchup!). Unarguably, the place to get a Chicago Dog is at Portillo’s – a long-time, well-known chain that originated in the city (and has now expanded across the United States). 

In addition to hot dogs, Portillo’s also serves fabulous Italian Beef Sandwiches – another must-eat in Chicago! However, if you are just going after the beef, then go to Al’s #1 Italian Beef – an iconic Chicago eatery chain that was established in 1938.

Alternatively, Join a Chicago Food and Drink Tour

While we have included some of the top must-eat restaurants in our Chicago in a Weekend Itinerary, there is still more feasting to do! Rather than choosing one place for lunch on the last day of your 3 perfect days in Chicago, taste-test your way through the city. Join an expert guide in the local foodie scene to discover favorite haunts and classic fare including Deep Dish Pizza, Italian Beef, famous Chicago Hot Dogs and more. Get the details here!

Explore Navy Pier Chicago

Complete your Weekend in Chicago Itinerary with an afternoon at Navy Pier. Like Pier 39 in San Francisco , Navy Pier caters mostly to tourists, but a fun and enjoyable time is had by all. Featuring a wide array of restaurants, souvenir shops and art exhibitions, Navy Pier is a must-see in Chicago…and a great way to end your Chicago 3-Day trip!

More Chicago Things To Do

We have outlined our best Chicago itinerary, including the top things to do when you visit Chicago in 3 days. Still, how to plan a trip to Chicago will depend on your specific interests. Therefore, we are sharing more fun things to do that you may want to add to your weekend trip to Chicago Itinerary.

Shopping on The Magnificent Mile

Visitors who want to go shopping in Chicago will find there is no shortage of stores! The best place to shop is on the famed Magnificent Mile, which is the section of Michigan Avenue that runs from the Chicago River north to Oak Street. The cosmopolitan street is lined with an astounding 460 retailers – from recognizable department stores to chic boutiques – and is a top destination for fashionistas planning a 3 Days in Chicago Itinerary.

Chicago Museums

With more than 65 museums in Chicago, there is certainly something for everyone. Whether it’s art, history or science that piques your interest, you can find a museum to include on your Chicago trip itinerary!

Chicago Trip Ideas: What Museums to Visit

When you plan trip to Chicago, it can be difficult to choose which museums to visit on your vacation. We are highlighting a few of the renowned museums to help you decide. 

Art Institute of Chicago: The city’s most famous art museum, the Art Institute is a top pick for 3 days in Chicago trips ( buy Skip-the-Line Tickets! ).

Museum of Science and Industry: The hands-on, family-friendly Museum of Science and Industry is a good museum to visit if you are planning trip to Chicago with kids. 

Museum of Contemporary Art: The fun and modern Museum of Contemporary Art is a fantastic museum to visit on a weekend getaway to Chicago. 

Shedd Aquarium: Whether you are planning a Chicago trip with family, as a couple or with a group of friends, the state-of-the-art Shedd Aquarium is a good addition to your Chicago vacation planner. 

The Field Museum: A fascinating museum of mummies and dinosaurs, the Field Museum is an excellent stop on a 3 day trip to Chicago. 

Adler Planetarium: If time permits in your itinerary, plan a day in Chicago that includes stargazing at the Adler Planetarium. 

Pro Tip : Save money and skip lines with a Chicago CityPass ! If you are planning on visiting more than one museum during your three days in Chicago, it will almost definitely save you money!

Go to a Theater Performance in Chicago

Need more ideas of what to see in Chicago in 3 days? Go to a show! Chicago has a vibrant theater district comprised of more than 250 theaters. From world-class productions to comedy acts, some of the best actors and comedians in the world have graced the stages in Chicago. 

Chicago Neighborhood Exploration

One of our favorite things to do in any city is explore the unique neighborhoods and districts. Throughout our Chicago weekend trip itinerary, we have featured some of the top Chicago districts – but we by no means covered them all. Some of the other places to explore in Chicago are Chinatown, Little Italy, Lincoln Park, Wicker Park, Boystown and Roscoe Village.

How Many Days in Chicago?

We think 3 days in Chicago is the perfect amount of time to get acquainted with the city…but we would have no problem entertaining ourselves for a week in Chicago – or longer!

How many days you spend in Chicago will ultimately depend on your interests, budget and availability.

Sample Chicago Itineraries 

We have outlined a perfect plan for a long weekend in Chicago – but what if your trip plans include more (or fewer) days? No worries! Using our 3-Day Chicago Weekend Itinerary as a base, we are sharing our best suggestions for longer and shorter trips.

1-Day Chicago Itinerary

Planning a Chicago in One Day Itinerary is not easy. The city has so many iconic sights and delicious things to eat that it is difficult to pick and choose which ones to include in your Chicago trip plan. However, if one day is all you have, then we suggest making the absolute most of it!

Chicago 1 Day Itinerary Trip Plan

For us, an ideal One Day in Chicago Itinerary would follow Day 2 in our above plan of what to do in Chicago in three days. However, unless you are passionate about baseball, rather than going to Wrigleyville we would recommend spending the evening on Navy Pier or in West Loop.

Chicago Itinerary 2 Days

With 48 hours in Chicago, visitors can plan a Chicago 2-Day Itinerary that is succinct and hits almost all of the highlights.

Chicago 2 Day Itinerary Trip Plan

If you are planning a 2-Day Itinerary for Chicago, we suggest following Days 2 and 3 of our outlined plan for what to see in Chicago in 3 days. Again, if the Cubs were not playing, we would skip Wrigleyville and spend the evening in West Loop, even squeezing in the Goose Island Brewery Tour if possible.

Chicago Itinerary 4 Days

Planning a 4-Day Chicago Itinerary allows for a lot more sightseeing – including many of the museums that we skipped in favor of neighborhood exploration. 

Chicago 4 Day Itinerary Trip Plan

To organize an ideal 4 Days in Chicago Itinerary, we would follow our Chicago 3-Day Itinerary – then, on the last day, we would use the CityPass to visit the top museums, including The Art Institute, Field Museum, Shedd Aquarium and Museum of Science and Industry.

Chicago Itinerary 5 Days

Spending 5 days in Chicago allows for a lot more adventures at a somewhat leisurely pace.

Chicago 5 Day Itinerary Trip Plan

To plan a perfect 5-Day Chicago Itinerary, we recommend following the above outlined Chicago 4-Day Itinerary – then, on the last day, spend the morning discovering a new neighborhood, go shopping on the Magnificent Mile in the afternoon and attend a theater performance in the evening – then get a drink at the Lobby Bar in the posh Palmer House for a nightcap.

Tips For Planning Your Trip to Chicago

Now that you know what to do in Chicago in 3 days, we have a few more essential tips for your trip!

Organize your Chicago Travel Plan

There is a lot more to Chicago trip planning than determining what to see and do. Don’t worry – we share our top tips for planning a vacation in Chicago – from how to get there to what to pack – in the next sections. 

As you research Chicago vacation ideas and start making reservations, make sure you stay organized. A useful travel planner – like our Printable Travel Planner – will help you keep track of all the details of your perfect Chicago travel itinerary! 

How To Plan Chicago Trip Budget

A trip to Chicago, Illinois can be expensive – but it doesn’t have to be. Travelers who are planning to spend a weekend in Chicago on a budget have many options for exciting entertainment. We suggest skipping sights with high-priced tickets and partaking in many of the cheap and free things to do in Chicago. 

Get our tips on how to plan the best budget trips – plus get our free Vacation Budget Planner – to help plan your budget Chicago, Illinois trip! 

How To Get to Chicago

An essential consideration for your Chicago trip itinerary is how to get there! Chicago can be reached by car, bus, train or plane. On our trips to Chicago, we have always arrived via plane.

Flying To Chicago

There are two major Chicago airports: O’Hare International (ORD) and Chicago Midway (MDW). Both airports have their pros and cons – O’Hare is an enormous airport serviced with flights from around the world ( London , Hong Kong , Tokyo , Munich , etc.), but is far from the city center. Alternatively, Midway dominated by Southwest Airlines and they service mostly US domestic destinations, but is much closer to downtown Chicago.

Both airports are connected to downtown Chicago via public transport (the Blue Line from ORD and the Orange Line from MDW), but visitors can also use taxis, Uber or private transport , too. 

Start your search for the best airfare and flight times on SkyScanner  – but first read our Top Tips for Finding Cheap Flights .

Trip To Chicago by Train

If you are traveling to Chicago from another city that is serviced by Amtrak, then you can also plan a Chicago 3 Days Itinerary with arrival by train. That said, the journey will likely take longer and could even be more expensive than flying – so bear that in mind as you make your trip plans! 

Getting Around Chicago

Downtown Chicago is very walkable – but getting to the districts outside the city center require transportation. Besides your own two feet, visitors have options when it comes to getting around Chicago – from the ‘L’ train to CTA buses to bikes to scooters to Uber and Lyft. 

Public Transportation

Chicago has one of the most extensive public transportation systems in America and makes getting around Chicago fairly easy. Both the ‘L’ train and buses have extensive networks. The affordable fares can be paid using a Ventra account – and both 1-Day and 3-Day flat fare tickets are available for your Chicago visit. Find Chicago Transit fare info here . 

More Ways to Get Around Chicago

That said, using Uber or Lyft is likely much more convenient – and if traveling in a group – not too expensive.

We do not recommend driving a car during your Chicago weekend itinerary; parking is a hassle and can cost a bundle.

Chicago Hop On Hop Off

The Chicago Big Bus provides an excellent service for travelers who want to easily get from one tourist site to the next. The Hop On Hop Off Chicago buses are double-decker, open-air vehicles that make stops at all top attractions – and include informative on-board commentary! Buy your ticket!

Where To Stay in Chicago

Although there are hundreds of places to stay in Chicago, for your Chicago vacation itinerary, we recommend choosing downtown accommodations.

Chicago Hotels

If you are going to splurge for 3 nights in Chicago, there is no better place than The Palmer House Hilton . The historic hotel, featuring a gorgeous lobby, is in a prime location within the Theater and Financial Districts near Millennium Park.

That said, there are hotels in Chicago that fit every budget and style. To find the perfect Chicago hotel for your stay, start your search on Booking.com – like we do. Use the filters to select the hotel amenities that are most important to you – and use the map to find the best location. Be sure to read all of our best tips for booking hotels !

3 Day Trip Chicago Vacation Rentals

In our travels, we often use Airbnb to find affordable apartments in the places we visit. In fact, we have found that Airbnb is sometimes less expensive – and offers more space – than most hotel rooms.

However, this is not always true on short stays. Be sure to check the extra fees when booking a short trip – like 3 days in Chicago – before confirming your Airbnb stay.

What To Pack For Your Chicago Trip

We have a few final tips and packing hacks for what to pack for your 3 perfect days in Chicago. Need a packing checklist? Grab your FREE Printable Packing Checklist here !

Weather Appropriate Clothing for Your Chicago 3 Day Itinerary

What you pack in your suitcase for a trip to Chicago will depend on the season. Winters can be frigidly cold, summers are often unbearably humid, springtime is wet and autumn is likely to be brisk, hot or soggy. So yes, the frequent weather changes make planning what to pack for your trip a bit of a conundrum.

If you are taking a Chicago summer vacation, pack loose-fitting clothes, a wide-brimmed travel hat and sunscreen . In the wintertime, you will need a winter coat, cozy cap  and gloves . And, if traveling in the spring or fall, make sure to bring a packable raincoat and travel umbrella . Because the weather can fluctuate, it is best to pack clothing that can be layered and carry a great day bag for quick wardrobe changes and all your everyday essentials .

Walking Shoes for Your Itinerary for Chicago

Our Chicago 3-Day Trip Itinerary includes a ton of walking! We recommend wearing a pair of comfortable walking shoes for trekking around the city. I like to wear these lightweight shoes by Columbia and Kris prefers wearing his Merrell trail shoes for city walks.

Travel Camera

Chicago is incredibly photogenic – and, if you are anything like us, you will be snapping a lot of pictures during your three days in Chicago. Instead of using your cell phone camera to capture the sights, we recommend upgrading to a real camera . We travel with a DSLR Canon Rebel and use an everyday 18-135mm lens . The camera comes bundled with tons of accessories – so it is perfect budget camera for beginners!

US Travel Insurance for Your Chicago Itinerary 3 Days

Travel insurance can be useful on all kinds of trips – even a long weekend in Chicago. It can cover unfortunate situations, like cancelled trips, lost luggage and more. Check rates and coverage on World Nomads .

Start planning your trip to Chicago, Illinois ! Search for the lowest airfares , the best accommodations and fun things to do …then start packing !   Want more travel planning tips? Head over to our Travel Planning page for more information and tips on traveling – and for country-specific information, take a look at our Travel Guides page !

Visit More Top Destinations In The USA

Planning other trips in the United States? Use our detailed guides to discover the best of cities across America (and some Underrated US Destinations ). In fact, we wrap up our top picks for the best places to go in our guide, 22 Weekend Getaways in the US !

Already have a destination in mind? We offer comprehensive guides for Phoenix , Columbus OH , Indy ,  Portland , Austin , Seattle , Boston , Denver and San Diego – to name a few! 

Up for a US road trip? Use the tips in our articles for the Oregon Coast , Columbia River Gorge , the California Coastline and through amazing Montana.

Find all of our tips for traveling in the United States on our USA Travel Destinations Page . 

We Want To Know: Do you have any advice on how to spend 3 days in Chicago? Is there anything you would add to our Chicago Itinerary? Give us your best tips on how to plan a Chicago trip in the comments below! 

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Finding the Universe

Travel tales, photography and a dash of humor

2 Days in Chicago – The Perfect Chicago Itinerary + Map and Tips!

Last updated: March 10, 2024 . Written by Laurence Norah - 3 Comments

In this guide, we’re going to share with you our suggestions for how to spend two days in Chicago.

As the third largest city in the USA, there is a lot to do in Chicago. There are world-class museums, a great selection of attractions, and some foods you just have to try.

There are also cultural sights, from first-class performance venues through to architectural history. Those of you visiting Chicago with family are also going to find plenty to keep you all entertained.

We have visited Chicago a number of times and always enjoyed our visits. Some of the museums in particular are absolutely world class, and of course we love the food!

As well as a detailed two-day itinerary for Chicago, this guide will also contain tips on where to stay, how to get around, how to save money when you’re in Chicago, tips on when to visit, and lots more. Let’s get started!

2 Day Chicago Itinerary

Our suggested two-day Chicago itinerary has you visiting the city’s top sights and attractions. This will have you seeing the main highlights of the city and visiting its most famous attractions and museums.

It’s a busy couple of days, and as with all our itineraries, we recommend you use it as the starting point for your planning. Feel free to add and remove items depending on your own interests and travel style.

Chicago Day 1

Your first day in Chicago has you going to the top of one of the world’s tallest buildings, learning about architecture, seeing a Chicago icon, and taking in some stunning art.

To get around, most of the sights on today’s part of the itinerary are within around 20 minutes’ walk of each other.

Of course, if you’d prefer not to walk, there’s a range of public transport options available, as well as a Hop on Hop off bus (included on the GoCity Chicago Pass ).

You can see more about getting around Chicago in a later section of this guide. Let’s get going with day 1!

Skydeck Chicago at Willis Tower

When we visit a city, I always love to get a bird’s eye view of it if I can to get a feel for the layout. One of the best places to do that in Chicago is at the Willis Tower (formerly known as the Sears Tower).

This massive 108 floor skyscraper dominates the Chicago skyline. When it was completed in 1974 it was the world’s tallest building, a title it held for almost 25 years.

It was originally known as the Sears Tower and the lower part of the tower was the headquarters of the retail company Sears. It was renamed in 2009 to the Willis Tower by the current lease of the building by British insurance broker Willis Group Holdings; however, many people continue to refer to it as the Sears Tower.

These days of course there are quite a few taller skyscrapers around the world. However, once you get to these sorts of heights, exactly where you are on the list doesn’t matter so much. What does matter is the view, and the Willis Tower definitely offers a good one from its Skydeck observation deck .

Found on the 103rd floor of the building, this is the highest observation deck in the United States. From here you can see all of downtown Chicago. On a clear day, you can actually see four states from here, although we’ve never had a day that clear when we’ve visited.

There is more to do than the views though. On your way to the elevators, you’ll pass through a series of exhibits which tell a brief story and history of Chicago. These are a lot of fun and there are some good photo opportunities as you pass through, so plan to spend around 30 minutes doing this.

At the Skydeck itself you’ll also find “The Ledge”. This is a collection of glass floored viewing areas which jut out from the main building, to give the feeling that you are floating right above the city. They make for an excellent (if slightly terrifying) photo opportunity, and access is included as part of your ticket.

The Skydeck is open year-round, and you can see opening times here . It gets quite busy, so we recommend visiting earlier in the day and booking a timed ticket in advance. A ticket is required, you can book this online in advance here .

The Willis Skydeck is included on the GoCity Chicago Pass and Chicago CityPASS .

There are a number of restaurants and shops located in the lower part of the building, known as the Catalog. So if you need a coffee or a bite to eat, you can definitely do that here.

Historic Buildings

Chicago is home to some iconic buildings and impressive architecture. Many of the buildings in the city are free to visit, and a number of these are within easy walking distance of the Willis Tower as you head towards your next stop. We think this can make for a nice way to stretch your legs.

There are of course many architectural highlights to choose from, but a couple of our favourites include the Rookery Building which features a Frank Lloyd Wright designed lobby and the Palmer House Hilton Hotel which has a gorgeous reception area.

Other interesting buildings in the area include the Chicago Board of Trade Building, Chicago Federal Reserve Building, the Monadnock Building (once the largest office building in the world), the Sullivan Centre, the Chicago Cultural Centre, and the Marshall Field and Company building (now a Macy’s).

You can also take a walking tour which includes a number of architectural highlights in this area, such as this one with the Chicago Architecture Centre .

A tour can be a good way to learn about what you are seeing, although of course you might need to tweak this itinerary to ensure they fit into your sightseeing schedule depending on when they run.

Millennium Park and Cloud Gate

If you walk from the Willis Tower via the buildings we recommend, you will find yourself on Michigan Avenue near Millenium Park .

Also, just for fun, if you walk down either E Adams St or E Jackson Blvd to where they meet Michigan Avenue, you’ll pass the start or end signs for historic Route 66 , which starts in Chicago and runs all the way to Los Angeles.

Ok, back to Millennium Park. This public park was opened in 2004 as a celebration of the third millennium. It’s home to a number of attractions, perhaps most famous of which is the Cloud Gate sculpture.

Nicknamed “The Bean” for its shape, this is a massive reflective stainless-steel sculpture by artist Anish Kapoor. It is a very popular location for photography, and is one of Chicago’s most recognisable icons.

You can walk all around and even under the sculpture, and the reflective surface makes for some fun photographic opportunities.

Millennium Park is free to visit and is open year-round. You can see more information about visiting on the official website here .

Note that the “Bean” is quite a popular attraction, so if you want to get photos without too many other people in you’ll want to come early in the day, ideally around sunrise.

There are other attractions in Millenium Park, including the Crown Fountain, Jay Pritzker Pavilion performance space, and the Lurie Garden. So you could easily spend quite a bit of time here. If you want to take in more green space, Millenium Park is found within Grant Park, which totals 319 acres.

However, our suggestion is instead to visit the Art Institute of Chicago, which is just south of Millenium Park.

Art Institute of Chicago

The Art Institute of Chicago is an epic art museum. We have visited a number of art museums all over the world, and this is definitely one of our favourites.

It’s a museum that will present you with a lot of “wow” moments. Whether that’s walking into a room with a whole wall full of Monet’s Haystacks, coming face to face with Grant Wood’s American Gothic, or seeing the evolution of Picasso’s style, we are sure you are going to have your breath taken away at some point during your visit as you realise you are looking at the original version of a recognisable classic.

Let’s talk some numbers and history. The museum was founded in 1879, and has a permanent collection of some 300,000 pieces. With a million square feet of space, it’s one of the world’s largest art museums, and second only to New York’s Met in the USA.

The collection, as already alluded to, covers a lot. In fact, there are around 4,000 years of art to explore, from Ancient and Byzantine through to Modern and Contemporary art. Almost every region of the world has some of its art represented.

Honestly, there are too many highlights to list them all. Suffice to say, even Ferris Bueller visited the museum on his day off , and we think it is a very worthwhile addition to your Chicago itinerary. Just be sure not to miss the Throne Miniature Rooms when you visit.

You can see opening times for The Art Institute of Chicago here . There’s a fee to visit, and it’s included on the Chicago CityPASS .

We actually visited on a guided walking tour like this , which was an excellent way to see the main highlights and get more of an appreciation for what we were seeing. Highly recommended if you would prefer a guided tour.

Chicago Architecture Cruise

On a recent visit to Chicago we asked our newsletter subscribers what they would recommend we do in the city. We got a lot of great suggestions but by far the most popular was to take an architecture cruise on the river.

Naturally, we followed this suggestion, and we can highly recommend that you do too. By this point your feet will probably want a break anyway, and spending around 90 minutes relaxing as the Chicago scenery winds by is an excellent way to relax.

There are a number of companies offering boat tours of the Chicago river. The majority of these are architecture cruises that last from 70 – 90 minutes.

Cruises generally have live narration, and as well as learning about some of the architecture that makes up the city skyline you will also learn a bit about the history of the city. Most cruises also have a full-service bar on board as well as restrooms.

We took this Chicago Architecture Cruise which was included on the GoCity Chicago Pass . Some other options to consider include:

• This 1.5 hour cruise
• This 2-2.5 hour river cruise which includes lunch, dinner or brunch

As you can see, there’s a wide range of options when it comes to cruising the river in Chicago.

To wrap up your first day in Chicago, we recommend you head out to Navy Pier . This 50-acre pier is just a few blocks east of the downtown Chicago area, jutting out into Lake Michigan.

Here you’ll find parks, gardens, shops, restaurants and rides. Our favourite ride to do here is the Centennial Wheel Ferris wheel, which sweeps you up into the sky above the pier and offers lovely views of the surrounding area and lake.

Other attractions include a carousel, the Chicago Children’s Museum, a huge funhouse maze and much more. There are also plenty of dining and drinking opportunities, as well as park space and public art.

We think Navy Pier makes for a fun end to a full first day in Chicago. It’s free to visit, but the rides and activities do have entry fees. The GoCity Chicago Pass includes some rides, including the Centennial Wheel. It also includes the Children’s Museum. Just be aware that many rides are seasonal and don’t run in the colder months of the year.

Chicago Day 2

It’s time for your second day in Chicago! Today we’re going to take in some more museums and sights around the city. Again, feel free to adjust the itinerary to your interests.

Today’s attractions are grouped in two areas of the city, one just south of the centre at Museum Campus, and one just to the north near Lincoln Park. Today you might choose to get around by Hop on Hop off bus (included on the GoCity Chicago Pass ).

Alternatively, public transit or taxis will get you between the main stops relatively easily. See the section of the post on getting around Chicago for some tips.

Museum Campus Attractions

Museum Campus is a 57-acre park which has a number of attractions. We would recommend picking one or two to visit as each is quite large and will probably take at least 2-3 hours of time to explore.

Of course, if you want to fit more in feel free to adjust this day to suit. Here are the three attractions on the Museum Campus we suggest you consider for your second day in Chicago.

Shedd Aquarium

If you are visiting Chicago as a family then the Shedd Aquarium should definitely be on your to-do list.

Opened all the way back in 1930, at the time this was the largest indoor aquarium in the world. Today, whilst it no longer has that title, it still has an impressive collection of 32,000 animals.

These range from fish and marine mammals through to birds, snakes, insects and amphibians. Basically, something for everyone. The upstairs area has a wide range of exhibits covering different habitats, whilst the lower levels are primarily devoted to the massive Oceanarium.

This is the largest indoor marine mammal facility in the world, with 3 million gallons of water. It’s home to beluga whales, pacific white-sided dolphins, sea otters and California sea lions.

There is a lot to see and do here, with a number of interactive exhibits as well as a 4D Theatre. There are also usually a number of special exhibits. You could easily spend more than half a day here if you wished!

The Shedd Aquarium is open year-round, and you can see opening times and a calendar of events on their website here . A ticket is required for entry, when we visited this had to be booked in advance. You can book on the official website here .

The Shedd Aquarium is available on the GoCity Chicago All Inclusive Pass as well as the Chicago CityPASS .

Adler Planetarium

A five-minute walk from the Shedd Aquarium will bring you to the Adler Planetarium , which is a must-visit for lovers of astronomy and space in general.

Like the Shedd Aquarium, the Adler Planetarium was opened in 1930. It was the first planetarium in the USA and is also a National Historic Landmark.

Of course, having a good history isn’t relevant if it can’t live up to modern day expectations. Thankfully, the Adler Planetarium has plenty to offer.

It has three theatres with a variety of programming, a variety of exhibitions which are dedicated to space science, an original Gemini program capsule, and a collection of antique scientific instruments.

All in all, there is plenty to see and do here to make it a worthwhile stop. The only thing to note is that it has more limited opening hours than some of the other locations on our list, so you will want to be sure to check when it is open prior to your visit, which you can do on the official website here .

Tickets can be purchased on the official website here . It is also included on the GoCity Chicago Passes as well as the Chicago CityPASS .

Field Museum

The third attraction we suggest you consider visiting at Museum Campus is the Field Museum .

This is one of the world’s largest natural history museums, and it has a huge collection of exhibits covering the natural world.

These naturally include a lot of dinosaurs, with Sue the T-Rex being a particularly popular attraction. You’ll also find exhibits covering animal, bird and plant life from around the world, geology exhibits, exhibits on the Ancient Americas and Ancient Egypt, as well as lots more.

A highlight for us was seeing the Tsavo Man-Eaters on display. This pair of lions gained notoriety for their killing spree on construction workers in Tsavo, Kenya, a part of the world we have been lucky enough to visit. Their story was told in the movie the Ghost and the Darkness , and it was interesting to see them at their final resting place.

Of course, there is a huge amount to see and do here, and like the Shedd Aquarium you could easily spend at least half a day here. It’s another popular place to visit as a family, so if you are in Chicago with kids then this should definitely be on your to-do list.

The Field Museum has an entry fee, and you can buy tickets online in advance here . It is also included on the GoCity Chicago Passes as well as the Chicago CityPASS .

Chicago History Museum

If you are interested in history, and haven’t already filled your day with museums, then we definitely recommend a visit to the Chicago History Museum .

This is found in the Old Town area of Chicago, where you will also be close to the free Lincoln Park Zoo .

If you are using the Hop on Hop off bus today this will get you most of the way, although you will have to walk the last few minutes. Alternatively, you can take public transport or a taxi.

This museum dates all the way back to 1856, when it was founded to study and document Chicago’s history.

By this point on your visit to Chicago you will likely have picked up some of the things that the museum covers, and here you will be able to get a more in-depth understanding of what made Chicago the city it is today.

From the Great Fire of 1871, to the civil rights movement, to the history of crime, industry and transportation in the city, the museum covers a great deal of both Chicago specific history as well as American history in general.

We really enjoyed visiting this museum, and think it is very much worth the visit. There’s a fee to visit, and you can book tickets online here . It is also included on the GoCity Chicago Passes .

360 Chicago

Your last stop for your time in Chicago is the John Hancock Centre, another of Chicago’s well-known tall buildings.

When this building was completed in 1968 it was the tallest building in Chicago, although of course the Willis Tower took over that title.

The main reason to visit is the 360 Chicago Observation Deck , found on the 94th floor of the building, just over 1,000 ft above street level. The viewing platform here is a particularly popular location to visit when it is dark, so you can see the city lights, although you get a great view of the city at any time of day of course.

As well as excellent views of the city skyline and Lake Michigan, you also have the option of riding the TILT attraction. For an additional fee, you can stand in a window that tilts to 30 degrees out of the building. We didn’t do this, but it looked like a lot of fun based on the reactions of the folks we did see doing it!

You can see opening dates and times for 360 Chicago on their official website here . You can buy tickets online here . It is also included on the GoCity Chicago Passes as well as the Chicago CityPASS .

That wraps up our main itinerary for Chicago. Of course, we missed a lot with only two days in the city.

There’s plenty more to see and do, from learning about Frank Lloyd Wright to visiting Hemingway’s birthplace to visiting one of the world’s largest science museums, another favorite of ours in the city.

If you have more time in the city, you’ll find lots to fill your time! However, you have at least gotten a good taste of the highlights.

2 Day Chicago Itinerary Summary

Here’s a quick summary of this itinerary for reference.

• Chicago Day 1 – Skydeck Chicago at Willis Tower, Historic Buildings, Millennium Park and Cloud Gate, Art Institute of Chicago, Chicago Architecture Cruise, Navy Pier
• Chicago Day 2 – Museum Campus Attractions (Shedd Aquarium, Adler Planetarium or Field Museum), Chicago History Museum, 360 Chicago

Chicago Itinerary Sightseeing Map

To help you visualise this itinerary, we’ve put together the below map which includes all the sights as well as our recommended hotels. You can also see this map on Google Maps here .

When to Visit Chicago

Chicago has a fairly variable climate, with hot summers and very cold winters. Some attractions are not open in the winter season, for example not all cruises operate and many of the Navy Pier rides are also closed over winter.

With this in mind, we’d recommend the best time to visit Chicago is going to be from mid-May through to mid-October. This will give you a better chance of good weather and attraction availability.

If you want to avoid the summer crowds, then May and early June, as well as September and early October are probably your best options.

It’s also worth noting that Chicago is a very popular city for conferences and large events, and when these are in town hotel rates can go up. So, when planning a trip, it is worth checking conference schedules online as these can definitely make the city a more expensive destination.

What to Eat in Chicago

When you think of Chicago, you probably think of some of the iconic food the city has to offer. Whilst Chicago has a huge range of cuisines to choose from, there are some quintessential Chicago dishes you should definitely try when you’re in the city. Some of these include:

• Chicago Deep Dish Pizza . Probably one of Chicago’s most famous foods, this dish was invented in Chicago. It’s baked in a pan, with the cheese under the tomato sauce, and it’s delicious. We’ve eaten it at both Pizzeria Uno (who claim to have invented it) and Giordano’s Pizzeria , and both were excellent. Definitely not to be missed.
• Chicago-style Hot Dogs . Whilst the hot dog wasn’t invented in Chicago, the city has its own unique take on the hot dog. Generally you get a beef sausage in a bun, with yellow mustard, chopped onion, sliced tomato, sweet pickle relish, a dill spear, and celery salt. There are loads of places serving good hot dogs in Chicago, we suggest checking out a branch of Portillo’s .
• Italian Beef Sandwich . Invented in Chicago, this is essentially a sub with slices of juicy hot roast beef inside. The sandwich is normally dipped into the beef juices, and often spicy pickled vegetables (giardiniera) are added to the top. This one can be found at most pizzerias and Italian-American restaurants.

Of course, there are many more incredible dishes to try in Chicago, with a comprehensive list of options available here . We don’t think you will go hungry.

One good option if you want to try a number of different foods and learn a bit about the history of Chicago is to take a food walking tour. We did this excellent tour with Devour Tours in Chicago , but there are a range of options to choose from.

How to Get Around Chicago

Chicago is a relatively easy city to get around. Many of the attractions are near the downtown area around the river, and can be reached on foot. Other attractions are either a short taxi ride away, or can be reached by public transport.

The most iconic public transport in Chicago (and also one of the easiest to use) is the “L” train. These elevated trains (hence the name “L”, for ELevated) cover most of the city, and fares are good value. You can even take the “L” all the way out to Chicago O’Hare International Airport, which is a great value way to get to and from the airport.

Taxis and ride-sharing apps can be convenient, however be aware that prices for the latter can vary dramatically based on time of day and vehicle availability.

For licensed taxis, they should use a meter but be sure to check before starting the journey as we have had drivers try to charge a high fixed fare for a short downtown journey. You can see the meter fares here .

There are also buses in Chicago, as well as the Metra commuter rail system which covers a wide area. You can find out more about getting public transport in Chicago on the Transit Chicago website.

When we visit Chicago, we normally find a combination of foot travel, L trains and taxis suits our needs best.

Another option is the Hop on Hop off bus . We always like to ride a hop on hop off bus, especially when visiting a new city, as it can be an easy way to get between sights and attractions and also to get a bit of information as we go.

Most of the stops on our itineraries are on the Chicago Hop on Hop off bus route, and it’s included on the GoCity Chicago Pass . Alternatively, you can buy hop on hop off bus tickets here .

Walking Tours of Chicago

We always enjoy taking walking tours when we visit a city, and Chicago is no exception. Walking tours can be a great way to learn about an area, a specific attraction, or the local cuisine from a knowledgeable local expert.

On a recent visit to Chicago we did two walking tours, a food walking tour , and a tour of the Chicago Art Institute . They were both excellent and we are happy to recommend them both.

Of course, there are more tours to try in the city. Here are some suggested options to check out.

•   This walking tour tells the story of Chicago’s most famous gangsters, as well as some of the city’s more famous ghost stories
• This ghost walking tour takes you through Chicago’s Northside district
• Food lovers will want to check out this food tour of Chicago culinary highlights , including pizza, hot dogs and Italian beef sandwiches
• If you have more of a sweet tooth, take a look at this donut tour of the city!
• Chicago is well known for its architecture. This guided tour of Chicago’s golden age architecture is an excellent introduction to that architecture
• Chicago is also home to a number of impressive street art pieces. This guided tour of Chicago’s street art is a great introduction to the scene.

If you do decide to take one or more of these tours, you may need to adjust this itinerary to suit of course.

Save Money with Chicago Attraction Passes

As you can see from our Chicago itinerary, there is a lot to see and do in the city. Unfortunately, whilst there are many free and low-cost options, most of the major attractions in Chicago have entry fees.

If you plan on visiting quite a few attractions during your stay then these will quickly start to eat into your budget.

The good news is that like most major cities around the world, Chicago has some great value attraction passes which can save you quite a bit on your entry fees.

There are three city attraction passes we recommend you consider for your time in Chicago. These are:

• The GoCity Chicago All Inclusive Pass
• The Go City Chicago Explorer Pass
• The Chicago CityPASS

Each of these passes works slightly differently and covers different attractions, so the right pass for you will vary depending on exactly what you want to visit. Let’s take a quick look at how these passes can save you money.

GoCity Chicago All Inclusive Pass

First, the GoCity Chicago All Inclusive Pass . This includes over 20 attractions in Chicago, including everything on our list with the exception of the Art Institute.

You buy a pass that is valid for a certain number of days, and then once activated at the first attraction, you can use the pass to visit the attractions it includes for the validity period.

For a shorter visit where you want to see a lot of attractions, the GoCity All Inclusive Pass probably makes the most sense. It includes the major, higher priced attractions such as the Chicago Architecture River Cruise, Hop on Hop off Bus, SkyDeck, Shedd Acquarium and lots more. This was the pass we used on a recent trip to Chicago.

GoCity Chicago Explorer Pass

Next, you might consider the GoCity Chicago Explorer Pass . With this pass, you decide how many attractions you want to include when you buy the pass, from 2 to 7. Then you can visit that many attractions over a 60-day period from the time you first use the pass.

This is a great option if you have a bit longer in Chicago and don’t want to see everything in a short period of time.

The notable exception on this pass compared to the GoCity All Inclusive Pass is that it doesn’t include the Shedd Aquarium.

We used the three-attraction version of this pass on a visit to Chicago where we had only a smaller number of attractions we wanted to visit, and it worked well to save us money on that trip.

Chicago CityPASS

Finally, another pass to consider is the Chicago CityPASS . We haven’t personally used this city pass in Chicago but we have used it in a number of other US cities and achieved great savings.

The Chicago CityPASS includes access to five Chicago attractions. Two  of these are fixed: the Shedd Aquarium, and Skydeck Chicago.

You then get to choose three more attractions from the following: the Field Museum, the Art Institute of Chicago, The Museum of Science and Industry, the 360 Chicago Observation Deck, the Shoreline Sightseeing Architecture River Tour or the Adler Planetarium.

This pass is valid for 9 days from the date of first use.

The Chicago CityPASS is a good option if you specifically want to visit just the attractions it covers. The main advantage it has is that it includes the Art Institute of Chicago.

Pass Comparison

We’ll look at a real-world example now to see which passes might save you money. I’ll use our itinerary to give you an idea of possible savings with each pass.

As of April 2023, the passes are priced as follows:

• A 2 Day Go City Chicago Pass costs $159 for an adult, and $99 for a child (aged 3-12)
• A 7 Choice Go City Chicago Pass costs $159 for an adult and $114 for a child (aged 3-12)
• A Chicago CityPASS costs $134 for an adult and $104 for a child (aged 3-11)

As you can see, all the passes offer a good saving if you plan on visiting a number of attractions. The savings will of course vary depending on which attractions you plan to visit, so you will need to decide in advance which those would be.

In summary though, if you plan to visit all the attractions in our itinerary, then the GoCity All Inclusive Pass will likely be the best option.

It covers all the attractions we mention, with the exception of the Art Institute. Even then, you are looking at over a $367.6 saving for two people, which is pretty impressive. Even if you skip quite a few attractions from our itinerary you are still likely to save a good amount of money.

However, if you plan on visiting fewer attractions or spending longer in the city, then one of the other passes might save you more money. It is also always important to check opening times, prices and any free opening days on the attractions you plan to visit to ensure you get the best deal.

Where to Stay in Chicago

Chicago has a good range of accommodation options, from hostels through to high-end five-star hotels. To minimise travel, we recommend staying closer to the downtown area if possible.

The area around the Art Institute, Millenium Park and the DuSable Bridge in particular will put you within relatively close walking distance of most of the attractions in our itinerary.

Note that prices can vary dramatically depending on time of year and if there are major events happening during your visit. If you are flexible with your travel dates it is worth trying different dates to see if prices change.

Below are our recommendations for where to stay in Chicago across a variety of styles and budgets. These are approximately ordered by price, from low to high, but pricing can change so do always check a few options before booking.

Centrally Located Chicago Accommodation Recommendations

• CitizenM Chicago Downtown – this is a well rated and centrally located hotel offering good value private en-suite rooms
• Hotel EMC2 Autograph Collection – found by Chicago’s famous Magnificent Mile, this is a well rated boutique hotel within easy walking distance to many attractions
• Congress Plaza Hotel – this 3* hotel is a classic, but it is showing its age a bit. However, it is very well located and can be great value for the location. We’ve stayed here and had a good stay.
• Pendry Chicago – this is a well rated and incredibly central hotel within easy walking distance of most of Chicago’s attractions
• The Peninsula Chicago – a very well rated and well-known 5* hotel in Chicago offering everything from an Olympic sized pool with city views to gorgeous en-suite rooms. An excellent high-end pick in Chicago.

Alternative Options

If you don’t mind being a bit away from the downtown, the following options are also worth considering. These will require a bit more transport time to reach most of the attractions.

• Chicago Getaway Hostel – found near Lincoln Park, this is a great value well rated hostel offering both private and shared accommodation options as well as a kitchen for guest use.
• Nobu Hotel Chicago – found in the trendy West Loop area of Chicago, this is a well reviewed five star hotel close to many excellent restaurants

Of course, there are many more options. You can see lots more options for accommodation in Chicago, including apartments, hotels, hostels and more, on booking.com here .

Further Reading

That’s it for our guide to spending two days in Chicago! We hope you found it useful.

To help you further plan your trip, we have a number of other resources we think you might find useful.

• We’ve visited a lot of other cities in the USA! See our guides to  things to do in Huntsville ,  things to do in Savannah ,  things to do in Charleston ,  things to do in Albuquerque ,  visiting New Orleans during Mardi Gras ,  things to do in Cambria ,  things to do in Houston ,  things to do in Dallas , and  things to do in Santa Fe  to get started!
• Chicago is the starting point for Route 66. Check out our 2 week Route 66 road trip itinerary for inspiration.
• If you want some more USA road trip inspiration, see our itineraries for a  USA Deep South road trip ,  California Road Trip , and  Pacific Coast Highway Road Trip
• To help you plan your trip to the USA, see our guide to how much it costs to travel in the USA , as well as  tips for driving in the USA  if this is your first time

And we’re done! As always, we’re happy to hear your feedback and questions to help you plan your visit. Just pop them in the comments below and we’ll get back to you as soon as we can.

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laura robbins says

13th July 2023 at 2:31 pm

Thanks, Laurence, for your quick reply. This information is very helpful and will make planning our Chicago trip so much easier than trying to do it alone!!

12th July 2023 at 6:40 pm

Dear Laurence & Jess,

I’m planning a visit to Chicago and have 3 nights but really only about 2 full days as part of one day will be travel and a meeting. I love your itinerary and everything in it sounds great but I would also like to visit Oak Park and see the Frank Lloyd Wright home. So I am wondering what you would suggest leaving out to have time for this? and if you have any suggestions on how to best do this visit to Oak Park with limited time? Do any Chicago passes include the Wright house/studio tour?

Greatly appreciate your great Chicago itinerary and any suggestions you have about above!

thanks, Laura

Laurence Norah says

12th July 2023 at 9:50 pm

Glad to be of help! So we visited the Frank Lloyd Wright home on a recent visit to Chicago and it was definitely worth it for those with an interest in the architect. I didn’t include it on this itinerary as I felt it was a bit of a stretch to get out here with two days, but it is certainly do-able.

In terms of what to skip, I’d say that the first thing to do is check if anything is closed on the day you are in town, as that might make your decision easier. Other than that I think it will likely come down to your interests. I’d say on Day 2 you could probably drop one or more of the museum campus attractions, and you could also skip either the 360 Chicago or the Skydeck Chicago attractions – one tower would probably suffice!

You can get out here using public transport, but we used an Uber because it was a lot faster. The tours are timed so you’ll want to check when they run and also opening times of course.

In terms of passes, it’s definitely included on the Go City All-Inclusive pass , which was what we used to visit it. Also included on that pass is the Ernest Hemingway Birthplace Museum which is just a few minutes walk from the Frank Lloyd Write home in Oak Park, and if you’re going to go all the way out here anyway you might want to add that on. We rang ahead to ensure we could get a tour at the times we wanted for both properties, I’d recommend doing the same.

If you choose to do both I’d suggest allocating at least four hours (so half a day) to account for getting out here, visiting the properties and getting back.

Let me know if you have any follow up questions or any more questions in general, we are happy to help if we can! Safe travels 🙂

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24 hours in downtown Chicago

With just one day to explore, you can make the most of your time with iconic, one-of-a-kind attractions and city experiences. Mix and match from the 10 itinerary stops below to create your perfect combination of restaurants, parks, museums, music, clubs, and rooftop views.

How to spend 24 hours in downtown Chicago: Stop 1: Visit Art Institute of Chicago Stop 2: See “The Bean” at Millennium Park Stop 3: Wander the Chicago Cultural Center Stop 4: See Buckingham Fountain at Grant Park Stop 5: Explore the lakefront Museum Campus Stop 6: Enjoy the view at SkyDeck Chicago Stop 7: Hear local legends at jazz & blues clubs Stop 8: Admire colorful street art Stop 9: Take an architecture river cruise Stop 10: Relax on the Chicago Riverwalk

Stop 1: A museum fit for Ferris Bueller

Anyone who loves the movie Ferris Bueller’s Day Off will know the Art Institute of Chicago . As you walk along Michigan Avenue, you’ll be greeted by two enormous bronze lions at the museum’s grand entrance. 

Once inside the Art Institute, you’ll experience one of the largest and oldest art museums in the United States, and one of the most expansive collections of Impressionist and Post-Impressionist artwork outside of the Louvre in Paris.

Make sure you visit the critically acclaimed Modern Wing, too, which houses an extraordinary collection of modern and contemporary masterpieces by Chagall, Dali, Matisse, Picasso, Pollack, Warhol, Magritte, and more. If you’d like to indulge in a little fine dining afterwards, head to Terzo Piano  on the Modern Wing’s upper level. In the summer, you can dine on the Bluhm Family Terrace amid rotating art installations and fabulous views of Millennium Park.

Stop 2: A giant bean and enormous rock climbing wall

Take the Nichols Bridgeway from the Modern Wing across to Millennium Park   and you’ll find an unprecedented combination of stunning architecture, sculpture, and landscape design all in one place. From the towering faces of Chicagoans at Crown Fountain to your own face reflected in the polished steel surface of Cloud Gate , aka “The Bean,” you’ll see exactly why Millennium Park is one of Chicago’s top bucket list contenders.

Exit Millennium Park via the BP Bridge, a 935-foot-long winding walkway that offers incomparable views of the Chicago skyline, Grant Park ,  and Lake Michigan. On the other side of the bridge sits Maggie Daley Park , a spectacular green space with massive rock-climbing walls, mini golf, picnic groves, tennis courts, and an amazing play garden. In the winter, the park’s in-line Skating Ribbon is transformed into a unique, meandering ice skating path. There’s another ice-skating rink at McCormick Tribune Plaza in front of “The Bean.” Over the summer months, ice makes way for a scenic outdoor patio right on the plaza.

Stop 3: A Tiffany jewel in the crown

On the corner of Michigan Avenue and Randolph Street, you’ll encounter the Chicago Cultural Center , a neoclassical landmark that houses the largest Tiffany stained-glass dome in the world. This stunning building is a humanities haven, with concerts, dance performances, theatre productions, films, lectures, art exhibitions, tours, and family events scheduled throughout the year — and all for free.

Stop 4: A waterfront landmark

Walking south and east through Grant Park , you’ll find yourself in the heart of a 319-acre green space, anchored by mesmerizing Buckingham Fountain . This Chicago landmark, one of the largest fountains in the world, was dedicated in 1927 and inspired by the Latona Fountain at the Palace of Versailles. Typically from early May through mid-October, the fountain produces a dazzling water display for 20 minutes every hour throughout the day. During these displays, a center jet shoots water to a height of 150 feet, with lights and music beginning at dusk.

Stop 5: Explore museum campus

Walking south from the fountain, head to Chicago’s legendary Museum Campus. This gorgeous green space directly on Lake Michigan and is home to three of the city’s most popular museums. The Field Museum will be the first museum you encounter and well worth a trip inside. It’s home to thousands of natural history artifacts spanning thousands of years, including the largest dinosaur ever discovered.

Shedd Aquarium  sits right next door. Here, in one of the largest aquariums in the world, you’ll meet 32,000+ aquatic creatures, including beluga whales, dolphins, sea otters, sea lions, penguins, stingrays, and sharks.

Just beyond the Shedd is Adler Planetarium , which, upon opening in 1930, became the first planetarium in the Western Hemisphere. The building is more than a museum; it’s a laboratory, a classroom, and a community exploring the universe together. Visitors flock to the Adler to experience interactive exhibits, live planetarium shows, hands-on educational programs, and world-class collections.

Stop 6: Views from towering heights

Sky deck at Willis Tower invites you to step on The Ledge, a glass box that extends approximately four feet from the building’s facade — over 1,300 feet above ground level. Willis Tower is one of the tallest buildings in the world, and, as you might expect, the views from Skydeck are amazing.

Stop 7: A music mecca or two

Two neighboring music clubs, one blues and one jazz, are must stops for the full Chicago experience. Buddy Guy’s Legends   was made famous around the world by its namesake, Grammy-award-winning blues guitarist Buddy Guy. There’s live music every night of the week, with free acoustic shows during lunch and dinner hours. Established in 1947, Jazz Showcase has hosted some of the greatest names in the business. The 170-seat club features local, national, and international acts nightly.

Stop 8: Picasso and Chagall on the street

Public art lives large in Chicago. And nowhere is this better seen than at Daley Plaza   and nearby Chase Tower Plaza. Picasso’s 50-foot-tall untitled sculpture takes center stage at Daley Plaza. When it made its debut in 1967, The Picasso , as it’s known, caused some controversy, with people comparing it to a large insect or baboon. Today, it’s an enduring symbol of Chicago itself.

At Chase Tower Plaza, Chagall’s monumental The Four Seasons   mosaic mural represents the arrival of spring, summer, winter, and fall. It’s composed of thousands of inlaid fragments in over 250 colors, and was created in Chagall’s studio in France before being dedicated to the city in 1974.

Stop 9: Architectural history on the waterfront

Head toward the river and you’ll find One Illinois Center, the Mies van der Rohe-designed home of the Chicago Architecture Center . Check out the to-scale skyscraper models in the Skyscraper Gallery and the approximately 4,200-piece immersive City of Chicago model on the main level, before picking the perfect architectural walking, bus, or boat tour at the center’s box office.

The Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady  is a crowd pleaser, and was voted Chicago’s #1 tour by TripAdvisor users. It’s led by knowledgeable Chicago Architecture Center docents who’ll tell you the fascinating history behind approximately 50 of the city’s iconic downtown buildings.

Stop 10: Relax along the river

The award-winning Chicago Riverwalk  is a 1.25-mile pedestrian stretch filled with coves, restaurants, bars, museums, public art, kayaking, boat excursions, bird-watching, fishing — and Art on theMART, the largest video projection art installation in the world. Illuminating over 2.5 acres of theMART’s river-facing façade, you can view the work of notable video artists from 7:15 – 9:15 p.m. Wednesday through Sunday, from March through April, and daily from May through December

Inside tip: Take a free Chicago Greeter tours

See Chicago like a local, with a local, with a free, customizable Chicago Greeter tour . Pick your neighborhood, theme, and language, then team up with a friendly guide who’ll show you both classic Chicago and its off-the-beaten-track gems. Book today .

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Looking for more to do in Chicago? Spend a day getting to know one of our vibrant neighborhoods.

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From this article.

Art Institute of Chicago

Tours & Attractions

Millennium park.

Maggie Daley Park

Accommodations

Chicago athletic association hotel.

Food & Beverage

Cindy’s.

Buckingham Fountain

Skydeck Chicago

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Chicago Riverwalk

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Home > United States > One Week in Chicago: Itinerary for 7 Days in Chicago

One Week in Chicago: Itinerary for 7 Days in Chicago

By Dymphe / June 11, 2023

One week in Chicago is wonderful. If want to get to know the city and see all the sights, then spending 7 days in Chicago is perfect!

You find Chicago in the state of Illinois. There's a lot to do and it's one of the largest cities in the United States . So exploring the city is definitely fun!

Chicago is a city with a beautiful skyline and many skyscrapers. The architecture is amazing, there are gorgeous viewpoints, and there are many sights.

When you spend one week in Chicago, you can get the best experience in the city.

For example, you can get an impressive view of the city at Skydeck Chicago. And you can go to the Art Institute of Chicago. Also, you can see beautiful nature, such as Grant Park.

And there's much more to do and to see during 7 days in Chicago! This itinerary shows you how you can make the most out of your time there.

Table of Contents

Getting to Chicago

You can get to the city of Chicago in various ways.

One of the best ways to reach the city if you are coming from a faraway place is by airplane. For your 7 days in Chicago, traveling by airplane can be very convenient.

There is an international airport in the city that makes this a convenient way to travel. Chicago O'Hare airport has routes from various airports in the US and other countries.

You can also travel to the city by train. This is convenient when traveling from destinations that are near the city.

Also, what's great is that you'll end up in the city center when you travel by train. This makes the rest of your one week in Chicago more convenient.

Traveling by bus is another way to reach the city. There are some bus companies with routes to the city. Some of these routes are very long if you come from places that are far. This isn't the most comfortable way to travel, but it is affordable.

Besides that, you can travel by car.

Where to Stay During One Week in Chicago

Staying in Downtown Chicago is best when you spend one week in Chicago.

That's because most of the sights of this itinerary are in this part of the city. When you stay there, it is easier to get around and you have more time to enjoy the city! Also, it's a lovely area with many restaurants.

Itinerary for One Week in Chicago

Let's start your 7 days in Chicago! This is going to be an incredible week with many amazing activities. You're going to get to know the city, see sights, visit museums, get beautiful views, and more!

Day 1: Sights, a View, and Art on the First Day of Your 7 Days in Chicago

The first day starts in Downtown Chicago. After that, you're going to see some sights and you'll go to a viewpoint. Furthermore, you're going to see art as well!

Walk Through Downtown Chicago

One of the best ways to start your one week in Chicago is by going to downtown.

Downtown Chicago is where you find many of the most famous sights in the city. You find here museums, historic buildings, and other great landmarks.

Also, you find here the skyscrapers of the city. And this is the part of the city where you can find many shops, restaurants, and entertainment.

Because there is so much in Downtown Chicago, this is a great place to experience the atmosphere of the city. And that's why it is a great place to start your 7 days in Chicago!

What's great is that you will often visit this part of the city when you go to specific sights, or when you go for dinner.

For now, I recommend going for a walk through this part of the city and enjoying all the things you see here.

See the City Hall

One of the landmarks that you can find in Downtown Chicago is the City Hall.

This is a very impressive building to see. It features a classic design that looks amazing.

Going here when walking through the city center is a must when you are one week in Chicago!

What I also like a lot about this building is that it forms a sharp contrast with the modern buildings in the city. This is great to see!

Have Lunch at the Revival Food Hall

Now that you are walking through the city, you likely want something to eat for lunch.

A great place for this is the Revival Food Hall . This is a food court where you find a variety of vendors selling all kinds of foods and drinks.

If there is a particular type of food you want for lunch, you likely find it at this place!

Because of that, it is also a great place to visit if you are with more people. Everyone can choose the food he or she wants, which is great! There will definitely be something you like.

See the City From Above at Skydeck Chicago

Done with lunch? Then, I recommend going to Skydeck Chicago . This is a must-see when you're 7 days in Chicago.

It is a lovely spot in the city center of Chicago from where you can see the city from above.

From up there, you can see all the buildings of the city from above, which is amazing to see.

You can get a panoramic view, which is awesome!

Also, you can experience The Ledge at Skydeck Chicago. This is a glass box that you can stand. Then, you can see the city of Chicago below you!

Visit the Art Institute of Chicago

You discovered Downtown Chicago, you had food, you saw the city from above, what's next? The last activity for this first day of your one week in Chicago is going to the Art Institute of Chicago .

The Art Institute of Chicago is one of the best museums in the United States.

You find here a permanent collection with 300,000 different art objects.

You find here artworks from all over the world. And there is art from a large period in time. This variety makes it a great place to visit for everyone!

Besides that, there are lots of yearly exhibitions that focus on a part of the collection. These are also very interesting, and they make the museum great to visit again and again.

Day 2: History, Nature, and More During One Week in Chicago

The second day of your 7 days in Chicago is going to be an amazing day. Today, you'll visit the Chicago History Museum, Lincoln Park, and Lincoln Park Conservatory. Also, you'll see a game at Wrigley Field!

Visit the Chicago History Museum

On the second day of your one week in Chicago, I recommend first going to the Chicago History Museum .

This is a great place to learn about the history of the city.

The museum has an extensive collection of objects that relate to the history of Chicago. It's very interesting to see the objects!

For example, there are many documents and photos. But there are also large objects, such as a railroad car and the first locomotive of Chicago.

Because of this, you find a lot of variety in the objects at this museum. And this makes the museum a fun place to go to!

Walk Through Lincoln Park

Close to the Chicago History Museum, you can find Lincoln Park.

This is a park where you can find a lot of nature, which makes this a very relaxing place to visit when you are in Chicago.

You can go here for a relaxing walk or you can sit down and enjoy nature that way.

What's also great is that there are many other things at the park. This makes it even better to go there when you're one week in Chicago.

For example, you find here playing fields, beaches, and many statues. This includes a statue of Abraham Lincoln.

Another interesting sight in the park is the Lincoln Park Conservatory. And that's where you should go next!

See the Lincoln Park Conservatory

You find here lots of beautiful plants that are wonderful to see! You can enjoy nature here by going for a relaxing stroll. If you like nature, this is one of the best activities during your 7 days in Chicago.

See a Game at Wrigley Field

To end this second day, I recommend going to Wrigley Field.

This is a baseball park that you can find in the north of Chicago.

You can see a match of the Chicago Cubs at this place. This is a Major League Baseball team!

When you are 7 days in Chicago, you should definitely see a game of the Chicago Cubs.

This is a lot of fun and it is a great way to experience another famous thing in the city!

Day 3: A Beautiful Walk, a Theater, and More

Today is going to be very fun. First, you're going to walk the Chicago Riverwalk.

After that, you're going to see the Wrigley Building. And you're going to visit the Museum of Illusions Chicago!

Furthermore, you're also going to see a show at the Chicago Theatre which is amazing.

Walk the Chicago Riverwalk

Let's start this third day of your one week in Chicago by going to the Chicago Riverwalk.

This is an area next to the Chicago River. You can walk here and go for a relaxing stroll along the river.

But there is more to this place than that!

You find here many places with street art, which makes the place very fun to see!

Furthermore, you find many restaurants and bars at the Chicago Riverwalk. So when you walk here you can stop somewhere for a drink!

See the Wrigley Building

When you walk the Chicago Riverwalk, you are likely to see the Wrigley Building. Especially if you like architecture, it's a must-see in the city.

This is an iconic skyscraper next to the Chicago River.

It has a unique architecture that is wonderful to see!

Furthermore, it is one of the most photogenic places in Chicago.

Have Fun at the Museum of Illusions Chicago

When you are in this part of the city, I recommend going to the Museum of Illusions Chicago .

This is a very fun museum to visit during your 7 days in Chicago!

You find here almost 100 different exhibits that show all kinds of illusions.

For example, there is a room where you look very large when you stand on one side, while you look small on the other side.

But there is much more! What's great is that many of the exhibits are interactive, which makes them more fun!

Besides that, you can also learn here about how illusions work. This makes the place both fun and interesting.

Also, this is a great place to visit for families.

Go to a Show at The Chicago Theatre

A great way to end your third day of this one week in Chicago is by going to the Chicago Theatre.

This is a historic theater that you can find in the city center of Chicago.

The history of the theater goes back to the year 1921. And in the past, it was a movie theater.

Nowadays, it is a performing arts venue. You can go here to see stage plays, speeches, comedy shows, and much more! If you are looking for a night full of fun, this is the place to visit in Chicago!

What's great is that besides the good entertainment, the venue itself is amazing too!

The architecture of the theater makes going here an even better experience! Outside, you can a large sign that shows the name of the theater. Moreover, the marquee of the theater looks great!

Also, the inside of the theater has a lot of ornaments and other elements that make the place look very charming!

Day 4: Contemporary Art, a View, and Water Tower Place

On the fourth day of your 7 days in Chicago, you're going to do great things. First, you'll visit the Museum of Contemporary Art. This is great if you love art. Also, you'll get a wonderful view of the city and you'll go shopping!

Go to the Museum of Contemporary Art

A great way to start your day is by seeing some beautiful art.

The Museum of Contemporary Art, Chicago is one of the best places in the city where you can do so!

This place is one of the largest art venues for contemporary art in the world.

You find here a very large collection of artworks from World War II till the present day.

At the museum, you find several changing exhibitions throughout the year.

These exhibitions combine works from the permanent collection with temporary artworks.

Many of the exhibitions featured works by famous artists, such as Jeff Koons, and Tom Friedman.

If you love contemporary art, this is definitely a great place during your 7 days in Chicago.

Get a View of the City at 360 Chicago

After seeing contemporary art, I recommend going to 360 Chicago .

At 360 Chicago you find an observation deck from where you can get a beautiful view of the city. You should definitely see this view during your one week in Chicago.

The observation deck is on the 94th floor, which is very high!

What's great is that you can see the city in all directions.

For example, you can see the skyline of the city next to Lake Michigan, which is awesome!

Another great experience you can have at this place is "Tilt".

Here you can tilt over the edge of the building and look down beneath you. This is an awesome experience!

What's great as well is that you can find a bar at the observation deck. This is the highest bar in the city. And this place allows you to have a drink with a panoramic view of Chicago!

Also, there are events at the observation deck. For example, you can do yoga classes with a view!

Go Shopping at Water Tower Place

Incredible art, incredible views, what's next?

You can go to Water Tower Place if you want to shop during your one week in Chicago.

You find here a shopping mall with lots of shops. In fact, you find here more than 100 shops. The number of shops allows you to spend a lot of time here if you want to!

Day 5: Visiting Beautiful Parks, a Museum and Adler Planetarium

The fifth day is going to be very beautiful. You'll go to wonderful parks and see the famous Cloud Gate. Also, you'll go to a museum and visit the Adler Planetarium.

Walk Through Grant Park

What's better than to start your day with a relaxing walk?

A great place to do that is Grant Park.

Grant Park is a large park that you find in the city center of Chicago. It lies in the business district of the city.

There are many walking paths that make it great to walk at this park.

Along the way, you see a lot of beautiful feats of nature. And there are also fountains, flowers, monuments, and much more.

Grant Park is also a great place to start your day with a run!

Go to Millennium Park and See Cloud Gate

Adjacent Grant Park, you find Millenium Park.

This is a small public park that the city created to celebrate the third millennium.

One of the most iconic landmarks that you can find here is Cloud Gate. As it's very famous, it's a must-see when you're 7 days in Chicago.

This is a sculpture made from polished stainless steel. The shape and the material are unique and great to see!

Another great thing in the park is the Jay Pritzker Pavilion.

This is a bandshell with 4000 seats and room for more on the lawn.

You can often find here concerts and festivals that are fun to attend!

When you spend one week in Chicago, I recommend checking if there is an event here, because it is so much fun!

Visit the Field Museum

Now it's time to see another one of the best museums in Chicago.

The Field Museum is a very interesting natural history museum.

It is one of the largest natural history museums in the world, and you should visit this museum for sure!

You find here a large collection of items.

The items include gems, meteorites, fossils, and dinosaur skeletons. But there is much more to see!

You can find the objects of the museum spread over several different halls.

For example, there is a hall that focuses on the Ancient Americas. And there is a hall that focuses on geology. Each hall is amazing to visit and worth going to!

Also, there is a museum library where you can find hundreds of thousands of books, photos, and more.

Go to the Adler Planetarium

Close to the last stop of this itinerary for 7 days in Chicago, you can find the Adler Planetarium .

This is a place where you can learn about astronomy and astrophysics.

You can find here space science exhibitions that feature many interesting objects. For example, you can find here the Gemini 12 space capsule.

Besides that, you find here three theaters where you can see films about space. The planetarium is a large dome with films on the ceiling while sitting on a seat that leans backward. This gives you an immersive experience that is incredible!

See a Show at the Arie Crown Theater

To end your day, I recommend seeing a show at the Arie Crown Theater .

This is one of the largest entertainment venues in the city.

You can go to this place to see a concert and have a very fun night!

In the past, many famous artists performed at this theater. For example, Frank Sinatra, The Jackson 5, and many others played here.

When you are 7 days in Chicago, you should definitely check out who's playing and go to a concert here!

Day 6: One of the Most Interesting Days during Your 7 Days in Chicago with Science, History, and Nature

Today is going to be an interesting day with science, history, and nature!

Go to the Museum of Science and Industry, Chicago

Another great museum to visit when you are one week in Chicago is the Museum of Science and Industry.

Going here is a great way to start your sixth day!

The Museum of Science and Industry, Chicago is a fantastic science museum!

You find here more than 2000 exhibits in a large number of halls.

Many of the exhibits are very large and include replicas and real objects.

For example, there is a German submarine captured during World War II by the allies.

Other interesting things to see here are aircrafts, airplanes, trains, and much more!

The museum is great if you want to see a lot of things!

Walk Through Jackson Park and Washington Park

Next to the museum, you find two parks that are great for a relaxing time when you spend 7 days in Chicago.

These parks are Jackson Park and Washington Park.

Both are great for a relaxing stroll, or if you want to hang out!

Do a Walking Tour of the City and Learn About History

After seeing interesting science objects and relaxing at the park, I recommend exploring!

You saw a lot of the city already, but there is a lot you likely didn't see or didn't learn about.

That's why you should definitely do a free walking tour of Chicago by Free Tours by Foot .

There are several tours to choose from.

For example, there is a tour that focuses on the architecture of the city.

What all tours have in common is that a local guide shows you around. Also, at the end of the tour, you can tip the guide what you think the tour was worth for you!

If you want to discover the food of the city, such as the Chicago deep-dish pizza, you can do a food tour!

These food tours aren't free, but they are definitely worth doing when you are one week in Chicago!

Day 7: Ending Your 7 Days in Chicago with Fun Activities

The last day is going to be very fun! You'll go to Navy Pier which is amazing. Also, you can go to the Garfield Park Conservatory and the Cadillac Palace Theatre!

Have Fun at Navy Pier

On this last day of your one week, you should go to Navy Pier for sure!

This is a pier that you can find at the waterfront of Lake Michigan.

You find here parks, a garden, restaurants, lovely attractions, and more things.

Because of these things, it is one of the most popular places in the city of Chicago.

The attractions on the pier are a lot of fun for the whole family.

You find here a maze, a drop tower, a carousel, and many other attractions.

Besides that, the garden that you find here is very beautiful to visit. The garden is a botanical garden with all kinds of beautiful plants. This makes going here during your one week in Chicago amazing.

Also, many festivals take place at Navy Pier.

For example, there is a winter festival from December to January. And in summer, you can see here evenings with fireworks. But there are many other events that are a lot of fun!

Go to the Garfield Park Conservatory

After having fun at Navy Pier, you should go to Garfield Park Conservatory for sure! This is a more relaxing activity.

This is a conservatory where you can see many plants from tropical places from all around the world.

For example, you find here palm trees that are great to see! Also, there are ferns and other types of plants.

You can go inside to see tropical plants, but there is also an outdoor garden that is worth seeing!

What's great is that you can also learn about the plants at this place. This makes it a very interesting place to go to.

See a Broadway Show at the Cadillac Palace Theatre

The Cadillac Palace Theatre is a great theater in the city where you can go for a fun night in Chicago! Going here is the last activity of your 7 days in Chicago.

You can see here Broadway shows that are a lot of fun.

What's great about this theater is not only the entertainment. Also, the theater looks amazing. For example, the interior of the theater is in the French Baroque style. This makes your experience here much better!

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7 Days in Chicago Itinerary: Discovering the City’s Hidden Gems

Chicago is an energetic city with a rich history of commerce and industry. If you’re planning a trip to the Windy City and want to make the most of your time, a well-planned itinerary can help. In this article, we’ll share a 7-days itinerary in Chicago as suggested by a local, covering some of the top attractions in Chicago — from the iconic Willis Tower to the beautiful Millennium Park and Art Institute of Chicago. This one-week itinerary can help you navigate the city whether you’re a first-time visitor or returning one.

About Chicago

Tips for staying in chicago.

Founded in 1833, Chicago has become a significant business hub in the Midwest region of the United States with over 2.7 million residents. It is a popular destination for tourists and visitors, with its wealth of landmarks, museums, and entertainment venues.

If you have never visited Chicago, here are just a few reasons to add it to your bucket list of travels:

• While there are numerous things to visit on land, the city is surrounded by one of the Great Lakes, where you may also participate in fun water activities.
• Chicago is a fantastic culinary city with some of the top restaurants in America. The city has world-class museums displaying everything from art to natural history to architecture.
• Millennium Park, which includes Cloud Gate (called “The Bean”), Buckingham Fountain, and The Crown Fountain, is one of the top free attractions. 
• The Taste of Chicago, Chicago Jazz Festival, Chicago Summer Dance, and Chicago Blues Festival are all annual festivals where you can enjoy free entertainment. 

Your budget will play a significant role in deciding which hotel to stay in during your stay. Generally speaking, the closer you are to the Loop and  Magnificent Mile , the higher the hotel rates. However, if you plan ahead you can score some great deals. Here are some tips for staying in Chicago that are recommended by a local. 

• Consider other neighborhoods, such as the far north, or even a suburb such as Oak Park, if your budget is limited. The location should also be easily accessible by train with a commute of no more than 30 minutes.
• Keep in mind major city events like Lollapalooza and holiday weekends like July 4th and Memorial Day. During these times, hotel rates will be extremely high. 
• Renting a car is not a good idea. Chicago parking is very expensive, with citations starting at $90. The cost of parking for a full day is about $25, while valet parking is even more expensive.  
• There are various options for getting around town, including car sharing (Uber, Lyft, Taxi), Chicago Elevator Trains (or the ‘L’), and city buses. More essential, make sure you understand how to navigate Chicago securely. 
• As with any city visit, keep vigilant and mindful of your surroundings. Never put yourself in danger when out exploring.

7 Days in Chicago Itinerary

Chicago’s attractions are seemingly endless, catering to all types of travelers. You can enjoy water activities in the Great Lakes or explore its diverse culinary scene in the many award-winning restaurants. Chicago is also home to world-renowned museums like the  Art Institute of Chicago  that showcase everything from art to natural history to architecture. Some of the city’s best attractions, such as the Cloud Gate, Buckingham Fountain, and The Crown Fountain, can be visited for free in Millennium Park. 

We think a good itinerary should have a nice mix of things to do that will not break the bank or wear you out. It should also stimulate the mind, body, and spirit of travelers. With that said, here is a 7-day itinerary for visiting Chicago that is recommended by a local. It is designed for you to see the city at a less frenzied pace and allow you to swap the activities so that they fit your preferences and interests.  

Morning : Start the day with a guided tour of the iconic Chicago architecture on the Chicago River Cruise. This is one of the most popular tours in Chicago and gives travelers a relaxing view of the city from a different perspective than a tour bus. 

Afternoon : Head over to the Art Institute of Chicago to admire world-famous works of art. You’ll see works of Impressionism, and modern art, as well as incredible sculptures from around the globe. 

Evening : Explore the historic Navy Pier, grab some dinner at one of the pier’s many restaurants, and take a ride on the Ferris wheel to see the city skyline. The pier is a great place to watch the boats float by or sit on the wave wall to relax. There is also free recreation in the summer ranging from bands to street entertainers. 

Morning : Enjoy a traditional Chicago-style breakfast at Lou Mitchell’s, famous for its pancakes, waffles, and omelets. It is one of the oldest restaurants and a great stop if you love diner food. Another great option for a phenomenal breakfast is Wildberry Pancakes & Cafe on Michigan Ave, or Little Goat Diner in the Fulton Market neighborhood.

Afternoon : Take a food tour of Chicago’s diverse neighborhoods, tasting everything from deep-dish pizza to hot dogs and Italian beef.

Evening : Experience the Chicago brewery scene with a visit to Revolution Brewing Company or Half Acre Beer Company. Optionally, if you prefer a glass of wine with musical performances, visit City Winery. There are two locations, one is downtown on the Chicago Riverwalk, the other is in the West Loop.   

Morning : Take a stroll on the Lakefront Trail along Lake Michigan. If you want to cover more sights in a short amount of time, there are bicycle rentals available at Navy Pier’s Bike and Roll, or you can find a station to use Chicago’s bike share program, Divvy. 

Afternoon : Visit one of Chicago’s beaches such as North Avenue Beach or Oak Street Beach and rent a paddleboard or kayak.

Evening : Watch the sunset over the lake while sipping a cocktail at a rooftop bar. Cindy’s Rooftop is located at 12 S. Michigan Ave and it’s near the Art Institute. If you visit the museum, dining at Cindy’s would be a nice option. Other nice rooftop bars in the downtown area include London House (85 E Wacker) and RAISED (1 W Wacker).

Morning : Visit the Museum of Contemporary Art Chicago to see modern and contemporary art exhibits.

Afternoon : Check out the National Museum of Mexican Art to learn about Mexican culture and art. It is in the Pilsen neighborhood and can be easily accessed via the pink line of the Chicago ‘L’ train. The elevator train is the best way to get around Chicago. Take the pink line west and exit at the 18th Street stop. The museum is a 7-minute walk from the station.    

Evening : Attend a performance at the world-renowned Chicago Symphony Orchestra . A classical performance would be an enriching cultural immersion while visiting the Windy City.

Morning : Start the day with a yoga class at one of Chicago’s many studios.

Afternoon : Pamper yourself with a spa treatment at the Peninsula Chicago or the Four Seasons. At these five-star hotels, you can indulge in luxurious amenities during your visit. Or visit the famed Kohler Waters Spa in Lincoln Park for a rejuvenating experience including massages, facials, and body treatments that are all designed to soothe and refresh both body and mind.

Evening : Enjoy a peaceful walk through the Lincoln Park Conservatory and Gardens. If you are traveling with kids or looking for nature and wildlife in the city, the Lincoln Park Zoo is one of many free amenities in Chicago. 

Morning : Take a tour of the legendary Wrigley Field. Are you traveling with sports enthusiasts or want to see the legendary field of the Chicago Cubs, then add this tour to your travel plans. Wrigley Field can be reached by the Red Line of the Chicago ‘L’ train (exit at the Addison station). The neighborhood is also a great area to explore for nightlife.  

Afternoon : Shop till you drop on the Magnificent Mile, Chicago’s famous shopping district. You can visit high-end designer stores like Gucci, Louis Vuitton, and Bulgari then stop at the World’s Largest Starbucks for a cup of joe after a late lunch.

Evening : Visit 360 Chicago for unparalleled views. From the observation deck, you’ll see Chicago to the east and Lake Michigan to the west. The TILT is an optional experience that suspends you over the city from the 94th floor.

Morning : Visit the iconic Willis Tower and step out onto the Skydeck for stunning views of the city. Compared to 360 Chicago, this observatory is from a higher point as the deck is on the 103rd floor. You can also enter the glass-floor observation for fun photos.

Afternoon : Take a stroll along the riverwalk to see the city from a different angle. If you tasted Chicago’s deep-dish pizza, stop at Lou Malnati’s (439 N Wells) or Giordano’s (730 N Rush) for some delicious pie from a pan. 

Evening : Experience the vibrant nightlife scene in Chicago’s Wicker Park neighborhood, with its many bars and restaurants. Exploring one of the city’s neighborhoods is truly for those with a sense of adventure. You can get to the area by taking the blue line Chicago ‘L’ train and exiting the Damen stop. Stop at Ina Mae (1415 N Wood) for great southern cuisine with a New Orleans vibe, or The Violet Hour (1520 N Damen) for a sophisticated artisanal cocktail with a speakeasy atmosphere. 

In conclusion, Chicago is a city full of life and entertainment. With this itinerary with recommendations from a local, you can be sure to have a great experience that most visitors would not know about.  Explore the suggested range of attractions, neighborhoods, and transportation options, and experience the best of the city! 

Has this 7 days in Chicago itinerary been helpful to you? Let us know in the comment section below!

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The Ultimate Chicago Family Vacation | 3 Days in Chicago With Kids

This post may contain affiliate links, view our disclosure policy .

Look no further for the ultimate Chicago family vacation itinerary perfect for spending 3 days in Chicago with kids!

The magnificent city of Chicago receives recognition as being the ‘Best Big City in the U.S.’, as well as being the ‘#1 World’s Best City for Having it All’ .

In this post, you’ll learn about what to see and do, how to get around, and how to plan a 3 day Chicago itinerary when visiting Chicago with kids.

In addition, our Chicago family vacation itinerary will guide you to the most popular things to do in Chicago while helping you plan the best visit ever!

The links on this page are Amazon affiliate links. If you click on the links and make a purchase, I receive a small commission at no extra cost to you.

Table of Contents

Chicago Family Vacation

If you’re wondering, “Is Chicago a good family vacation spot?”, I would overwhelmingly say, “Yes!”.

In fact, if you’re familiar with popular urban vacation destinations, it’s more than likely that Chicago is on your  US bucket list !

Located on the shore of Lake Michigan in Midwest USA, Chicago, Illinois is a glorious city with a population of 3 million people.

Chicago is a tourist’s dream as it has a magnificent, walkable downtown area filled with gorgeous parks and sculptures, impressive museums, several  famous Chicago foods , and beautiful lakeside views.

Perfectly blending the hustle and bustle of city life with a degree of friendliness that you’d expect from a small town, this diverse area is a must-visit metropolitan wonder.

Whether you’ve dreamed of walking through Millennium Park and photographing “The Bean” or you want to enlighten your kids by checking out the ever-popular Adler Planetarium, there are so many family-friendly Chicago attractions!

Oh, and psst…we LOVE Chicago so much, that we’ve written several other guides to help you plan your trip!

• What to Wear in Chicago: A Visitor’s Guide for Every Season!
• What to do in Chicago in Winter (+ 3-Day Itinerary)
• Top 5 Kid-Friendly Restaurants in Downtown Chicago
• 25 Things to do in Chicago at Night
• A Complete List of Things to do at Navy Pier Chicago
• Famous Chicago Food: 5 Iconic Chicago Foods to Try!

Best Time to Plan A Chicago Vacation

The best time for a Chicago family vacation is during the months of May, June, September, and October.

In other words, plan a family trip to Chicago when the weather is mild during the late spring, early summer, and early fall.

In addition, be sure to consider what to wear in Chicago depending on when you visit, as the weather varies drastically.

Though Chicago in summer can be hot and humid, many are drawn to the area during this time in order to take advantage of its lake activities and outdoor events.

Keep in mind, however, that Chicago gets very busy with tourists over the weekends and holidays.

We just so happened to visit Chicago in September over Labor Day weekend.

Though the sidewalks throughout the city were very crowded, the holiday weekend special events still made this a great time to visit.

Additional planning tip: If you’re not afraid to get bundled up and brave the cold, we’ve found that visiting Chicago in winter can be just as fun!

Read here to learn about our winter getaway in Chicago which includes the best things to do in Chicago in winter .

Chicago Family Vacation Itinerary: Day 1

The following breakdown of several family activities in Chicago can be applied to a two-day itinerary for Chicago, or extended to a 4-day Chicago itinerary.

Either way, here are our favorite Chicago vacation ideas that we’ve done time and time again.

• Arrive in Chicago and admire the beautiful Chicago skyline
• Check-in to your hotel
• Have dinner at the iconic Portillo’s Hot Dogs

Arrive In Chicago

Day 1 of our 3-day Chicago family itinerary involved a 6-hour drive from our hometown (We love road trips!)

We found travel down Interstate 90 and into the heart of downtown Chicago to be an absolute breeze, with the exception of heavy traffic at times.

Considering driving to the Windy City too?

We have compiled essential tips on how to master a family road trip , and how to create “Are We There Yet” goodie bags to help make it the best road trip ever!

Check-In To Your Hotel

For this Chicago family vacation, we stayed at the Best Western River North .

Best Western River North is centrally located to several downtown Chicago points of interest.

It is also really close to some great places to eat with kids, such as the SafeHouse, Portillo’s, McDonald’s, and Hard Rock Cafe.

Also adjacent to Best Western River North is a BP gas station and Walgreen’s pharmacy and convenience store.

Check-in was quick and efficient and the front desk staff was very friendly.

They even offer free ice cream sandwiches and sherbet push-ups around the clock!

Like most hotels downtown, there is a daily fee to park on-site. The lot is staffed by a parking attendant and is safe and secure.

Our room was comfortable and stylish; just large enough for 2 double beds and an additional cot. The hotel itself has a heated indoor swimming pool on the top floor.

Next to the pool is an outdoor rooftop deck with comfortable lounging chairs and amazing views of the city.

We loved taking a glass of wine up to the deck each night to relax while the kids swam. The presence of the rooftop deck was definitely the best selling point for us.

Breakfast is not included at Best Western River North, but for a small cost, you can visit the onsite restaurant for made-to-order breakfast items.

Portillo’s

No family trip to Chicago is complete without experiencing the 5 famous Chicago foods that are the cornerstone to every visit.

Being right across the street from our hotel, Portillo’s was an easy choice to start off our epic Chicago food experience.

What started as a hot dog cart, Portillo’s restaurant serves up Chicago-style hot dogs, Italian beef sandwiches, burgers, salads, and other sides.

Their casual atmosphere, amazing food, and welcoming ambiance make this one of our most recommended kid-friendly restaurants in downtown Chicago .

Additional planning tip: If you’re looking for a complete foodie experience, schedule a Chicago Food Planet walking food tour that covers the Chicago hot spots.

Chicago Family Vacation Itinerary: Day 2

• Walk and shop on Magnificent Mile
• Take an Architectural River Cruise
• Have lunch at Wildberry Pancakes and Cafe
• Tour and take photos in Millennium Park
• Spend time enjoying Navy Pier

Magnificent Mile

Start off your Chicago family trip by grabbing a cup of coffee and taking a leisurely walk along Chicago’s Magnificent Mile .

Magnificent Mile is the nickname of the long stretch of upscale shops and restaurants located along Michigan Avenue.

It is also home to the world-famous John Hancock building (home to 360 Chicago and TILT) and the historic water tower and pumping station that were two of the only structures to survive the Chicago Fire of 1871.

Walking along the bustling sidewalks of the Magnificent Mile is not to be missed in your Chicago 3 day itinerary.

Kid-friendly stops include the Disney Store, American Girl Place, Chicago-famous Garrett P opcorn , and Dylan’s Candy Bar.

Chicago 3 day itinerary planning tips: Depart your hotel at 9:30 AM on foot.

Plan to spend 20 minutes walking the entire Magnificent Mile from north to south, with additional time allotted for your choice of shopping and stops.

View this post on Instagram Our experience on Chicago Architecture Center’s River Cruise aboard Chicago’s First Lady was nostalgic, informative, relaxing, and overall AMAZING! So thankful for this opportunity! #choosechicago #cruisechi2019 #cruisechicago #cafcrivercruise #travelwithaplan #TWAP #familytravel #chicagowithkids A post shared by Jennifer Brommer (@travelwithaplan.jen) on Aug 31, 2019 at 5:50pm PDT

Architectural River Cruise

If you’re looking to plan a family vacation in Chicago, IL, our top recommendation is to get tickets to go on a Chicago architecture river cruise (if the weather and season permit).

After walking down Magnificent Mile to the south, you will come across the Michigan Avenue Bridge and Chicago’s Riverwalk.

Here is where you access the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady .

For GPS directions, use 112 E. Wacker Drive and look for their blue awning marking the stairway down the river walk dock.

Though there are a few other river cruise options, we absolutely loved our experience on the CAFC River Cruise and highly recommend it.

The boat was family-friendly, fun, and nostalgic, and the commentating was highly informative.

There is a full bar aboard that includes snacks, drinks, and cocktails.

Imagine a glorious float down the Chicago River learning about the towering skyscrapers – while sipping a Mimosa with Tony Bennett music playing in the background.

Chicago family vacation planning tips: Secure 10:30 AM CAFC River Cruise reservations .

Pick up your tickets at 10:00 AM and get in line no later than 10:15 AM to be the first to board the First Lady.

Seats are not pre-assigned and are first-come-first-serve.

Choose seats on the upper deck along the sides for the best-unobstructed photo ops.

The entire river cruise lasts 90 minutes.

Millennium Park

No vacation in Chicago would be complete without visiting Millennium Park! In addition, if you’re planning a family trip to Chicago on a budget, it’s nice to know that all of the attractions in Millennium Park are free!

After stopping for lunch at Wildberry Pancakes and Cafe , spend plenty of time visiting Chicago’s iconic Millennium Park .

Here is where you will find the most talked-about (free) attractions that people typically refer to when visiting Chicago.

Each of these attractions should be part of any Chicago trip with the family!

The most popular attraction in Millennium Park is the Cloud Gate sculpture.

Commonly referred to as ‘The Bean’, Cloud Gate is an art piece that is a great place to take Instagram photos and selfies, especially off of its reflective surface.

You can see the reflection of the Chicago skyline, walk under The Bean, and take photos from all sides.

Despite the crowds, the space is large enough to accommodate large amounts of visitors.

(It is highly unlikely to get a photo without other tourists in it, however.)

Crown Fountain

Another highlight of Millennium Park is Crown Fountain .

Here, two huge 50ft LED screens light up while displaying the faces of average Chicago residents.

Every 5 minutes, the mouths of the faces spill water onto the ground creating a shallow reflective pool.

The fountains make a great place for kids to cool off in the hot summer months.

BP Pedestrian Bridge

The gigantic stainless steel BP Bridge connects Millennium Park to Maggie Daley Park.

Though there are other outlying sidewalks to get to Maggie Daley Park, make it a point to walk across this unique pedestrian bridge.

Its shiny silver surface, snake-like curvature, and prize-winning architecture make it an experience to remember.

Maggie Daley Park

As one of the most kid-friendly Chicago activities, be sure to visit Maggie Daley Park!

After crossing BP Pedestrian Bridge you will enter Maggie Daley Park .

Here you will find mini-golf, a climbing wall, and 5 playgrounds themed for different ages and abilities.

Large tube slides for older kids, innovative swings, and a splash fountain for younger ones are a few other highlights.

The rolling hills and valleys of rubber turf, as well as perfectly incorporated green space, make this a dynamic area that will keep kids entertained for hours.

For those families with small children or kids of all ages for that matter, Maggie Daley Park is a must-do during your Chicago itinerary.

Lakefront Trail

Upon exiting Maggie Daley Park and heading towards the water you will come across an entrance onto Chicago’s Lakefront Trail .

Chicago’s scenic Lakefront Trail is an 18-mile paved trail that follows along the shoreline of Lake Michigan.

With separate lanes for walking, running, and biking, head north on this trail from the Millennium Park area to get to Chicago’s Navy Pier.

The 15-minute walk along Lakefront Trail will allow you to admire Lake Michigan and watch the on-water boats, kayaks, and wildlife.

Chicago family vacation planning tip: Plan to spend 1-2 hours visiting Millennium and Maggie Daley Park.

You may need more time if you have smaller children who want to spend more time at the park.

When considering what to do in Chicago in 3 days, no family itinerary is complete without a visit to the historic Navy Pier .

Over the past few years, Navy Pier has become one of the most popular things to do in Chicago as well as is one of the best Illinois attractions for families.

Likewise, there are literally so many things to do at Navy Pier Chicago with kids!

Ride the 200ft tall iconic Centennial ( Ferris ) Wheel and other outdoor amusement rides, or dine at one of its many restaurants.

Other activities at Navy Pier include the Amazing Chicago Funhouse Maze, Virtual Rush: Chicago virtual reality experience, and Lake Michigan sightseeing cruises.

Additional planning tip: If you’re looking for things to do in Chicago at night , save riding the Centennial Wheel for when the sun goes down!

Riding the Centennial Wheel at night is super fun and provides amazing views of Chicago’s lit-up skyscrapers!

View this post on Instagram One of the biggest highlights of our recent trip to Chicago was the #Chicagofoodplanet Signature Food Tour @ Navy Pier! Our amazing host Faith treated us to Navy Pier’s finest eats without having to wait in lines, and while humor and hospitality! A-MAZING! #chifoodplanet #chifoodplanettours #chicagofood #navypierfoodtour #navypier #chicagowithkids #foodplanet #travelwithaplan #TWAP #familytravel #bestplacestogo A post shared by Jennifer Brommer (@travelwithaplan.jen) on Sep 4, 2019 at 10:21am PDT

*Click here for our exclusive FREE Family Vacation Packing List that is both customizable and printable!

Chicago Family Vacation Itinerary: Day 3

• Visit 360 Chicago and ride TILT
• Take a Chicago Big Bus tour
• Have lunch at Giordano’s Pizza
• Tour the Art Institute of Chicago
• Attend a Blue Man Group Chicago show
• Have dinner at SafeHouse Chicago

360 Chicago Observation Deck + TILT

Start off this morning of your Chicago 3 day itinerary by walking through the north end of Magnificent Mile via Michigan Avenue (to Water Tower Place).

Here you find the (former) John Hancock building, which is home to the 360 Chicago Observation Deck and TILT.

Located on the 94th floor, the 360 Chicago Observation Deck provides unparalleled views of Lake Michigan and the Chicago skyline.

[Included in the Chicago CityPass ]

It also offers interactive learning opportunities, a gift shop, and a modern bar and cafe.

For an additional cost, visitors of the Observation Deck can ride TILT.

TILT involves stepping onto a moving platform that slowly tilts you – in a standing position – outside the side of the building.

As you hold onto metal bars, the platform moves outward in 3 increments until you are angled in suspension over Michigan Avenue and the buildings below.

Chicago itinerary planning tip: We had 9:00 AM reservations for 360 Chicago. This is a very popular Chicago attraction so I recommend visiting in the morning as such when crowds are fewer.

Plan to spend 45 minutes to 1 hour here.

Chicago Big Bus Tour

If you’re planning a trip to Chicago, we highly recommend doing a hop-on-hop-off Big Bus Chicago tour as a way to learn and see more of the city.

Tickets for Big Bus Chicago can be purchased online or at any of the advertised Big Bus stops .

There are 2 Big Bus Chicago stops on the same block as the John Hancock Building, so this is where we boarded and began our hop-on hop-off experience.

Chicago itinerary planning tip: It is important to refer to the Big Bus Chicago route map to plan the places and timing of your stops.

The lower half of the bus provides covered seating, while the top half of the bus is open air.

Rain ponchos are provided free of charge in the case of rain.

Giordano’s Pizza

After boarding Big Bus Chicago at Stop #12, we rode continuously to Stop #4 at Millennium Park.

Here, we got off and headed for lunch at Giordano’s Pizza (130 E Randolph St, Chicago).

After having a slice of their famous deep-dish pizza while on the Navy Pier, we fell in love.

We couldn’t end our Chicago vacation without another round of this authentic Chicago-style pizza .

Additional planning tip: Plan to spend 1.5 hours at Giordano’s as the pizza alone take 45 minutes to bake.

Art Institute of Chicago

After lunch, we passed through Millennium Park to the adjacent Art Institute of Chicago .

One of the world’s greatest art museums, the Art Institute of Chicago goes out of its way to cater to families (+Kids under the age of 14 are free).

Our favorite family-friendly aspect was the Family Room.

Here, we got to create a customized family museum tour using the interactive Journey Maker.

Chicago itinerary planning tip: The Art Institute of Chicago is massive so plan to spend 60-90 minutes there, depending on the attention span of your kids.

Don’t forget to see Picasso’s, The Old Guitarist, and Grant Wood’s, American Gothic.

Blue Man Group Chicago

After finishing our tour of the Art Institute, we grabbed an Uber and headed to the Briar Street Theater.

Briar Street Theater is home to Blue Man Group Chicago , and is stop #5 of our Chicago 3-day itinerary!

Having heard so much about Blue Man Group , we were so excited about this unique experience.

In fact, as soon as we stepped into the bustling dark theater adorned with blue spotlights, we knew we were in for a treat.

A performance filled with music, art, obscurities, and crowd interaction, the Blue Man characters wow the crowd without ever speaking a word.

Never knowing what is going to happen next, the performance is highly engaging and keeps you at the edge of your seat.

This unforgettable experience is a must-see upon your next family trip to Chicago!

Chicago itinerary planning tip: We had 2:00 PM reservations for Blue Man Group Chicago.

The performance lasts 90 minutes with no intermission.

Uber drivers were readily available to take us back to the downtown Chicago area once the show was over.

Additional planning tip: If you’re looking for another Chicago activity that teens will love, check out Escape Game Chicago! Though we have not personally done one, the downtown Chicago location offers 5 different 60-minute escape rooms!

SafeHouse Chicago

(This location is temporarily closed due to the effects of the pandemic; check their website before visiting.)

After heading to the hotel to rest and get changed for dinner, we walked 5 minutes to our much-anticipated dining experience at SafeHouse Chicago !

Once arriving at the secret entrance, couples, families, and groups are welcomed in one-by-one and must give a password in order to be granted access to the restaurant.

If you do not know the password, silly actions must be performed in order to be let in while the rest of the visitors in the restaurant watch on.

Once inside, the dark, spy-themed decor and lighting are uniquely inviting.

Upon being seated, you are immediately given a name tag to identify your ‘agent name’. This is the name that the servers will refer to you as during your dining experience.

After ordering off the menu, children may participate in an interactive scavenger hunt or visit the in-house magician while waiting for their food.

Chicago itinerary planning tip: Due to its popularity and that it is one of the best Chicago restaurants with kids, reservations are highly recommended at SafeHouse Chicago.

Also, you should know that t he fun doesn’t end once your meal is complete. (There is a mysterious twist in getting out of the actual restaurant.)

Chicago CityPASS

There are literally so many things to do in Chicago that many people wonder about Chicago family vacation packages.

One of our best travel tips is that if you’re trying to see the best of Chicago in 3 days, the most affordable way to see the city is with the  Chicago CityPASS .

In fact, you can save 50% on visiting Chicago’s top 5 attractions with this one purchase alone.

Grab your CityPASS here  – you will not regret bundling your activities into this Chicago family vacation package.

Additional planning tip: Most of the museums have a separate entry and line for CityPASS holders which will also save you a great deal of time.

Chicago Family Vacation: Getting There

If you’re heading to Chicago with family, visitors typically travel there via plane, train, bus, or personal vehicle.

Chicago’s central location and the fact that it is accessible by many major interstates and highways make it easy to get there by car.

Be aware that there are several Illinois tollways as you drive into the city, so be sure to have spare dollar bills on hand.

If traveling from a farther distance, however, search for flights into either O’Hare International Airport or Chicago Midway International Airport.

How to Get Around Chicago

Chicago is a walkable city meaning that when staying downtown, the majority of the popular restaurants, sites, and attractions are all within walking distance to one another.

If staying downtown you simply do not need a car to get around once there.

For longer stretches, Uber vehicles are highly prevalent and can typically be found within 2 – 3 minutes of any given address.

In addition, Chicago is well-known for its convenient street system and its fantastic  public transit system .

Where to Stay in Chicago

If you’re planning a vacation in Chicago, IL, there are several options on  where to stay in Chicago .

Regardless, be sure to stay downtown so that you can do as little driving around as possible.

Choices downtown include staying within the Magnificent Mile, The Loop, or River North neighborhoods.

The Magnificent Mile is close to the John Hancock Building, Navy Pier, and upscale shopping.

The Loop is close to the Willis Tower and Millennium Park.

On the other hand, River North hotels are still within walking distance to major attractions but provide more budget-friendly options that often include pools and free breakfast.

Here are some of our favorite  Chicago resorts for families:

• Embassy Suites Chicago Downtown Magnificent Mile
• Embassy Sites Chicago Downtown
• Courtyard Chicago Downtonw/Magnificent Mile
• Homewood Suites Chicago Downtown/Magnificent Mile

Chicago Family Vacation: If You Have More Time

If you’re fortunate to be planning a Chicago 4-day itinerary, you’ll have time to do a few extra things.

The one area of downtown that we did not get to experience was the extremely popular Museum Campus which is home to several world-famous Chicago museums.

Places such as the Shedd Aquarium, the Field Museum of Natural History, and Alder Planetarium, are places that we will definitely visit during our next family vacation to Chicago.

The Museum of Science and Industry is another Chicago family favorite and should be considered if you like science and technology.

An important note is that both the Museum of Science and Industry and The Field Museum are both sensory-friendly Chicago activities for visitors with autism or sensory processing disorders.

[All Included in the Chicago CityPass ]

Thank you to Choose Chicago, Best Western River North, Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady, Chicago Food Planet’s Signature Food Tour at Navy Pier, 360 Chicago and TILT, Art Institute of Chicago, Blue Man Group Chicago, and SafeHouse Chicago for hosting our family’s visits. I was not compensated for this Chicago 3 Day itinerary article. All opinions are my own. Jen

If you like our Family Chicago Vacation itinerary, here are our related posts to help plan your trip:

• 25 Exciting Things to do in Chicago at Night
• Famous Chicago Food: 5 Foods You Must Try During Your Visit
• Top 5 Kid-Friendly Downtown Chicago Restaurants that Your Family Will Love
• What to Wear in Chicago: A Visitor’s Guide For All Seasons
• Top 10 Things to do at Navy Pier Chicago with Kids
• Our United States Bucket List: 15 Exciting Places For Families to Go

*Before leaving, be sure to check our Travel Resources Page to find exclusive travel discounts and to book hotels, rental cars, and guided tours.*

Jen Brommer is a family travel expert. She has been featured as an authority on several notable travel websites and is a member of the Family Travel Association (FTA), Midwest Travel Network, and TravMedia global media network.

A prominent content creator and influencer on Instagram, Jen has over 150K unique monthly blog readers from countries all over the world. She has spent the last 16 years planning fun, and hassle-free family vacations for her family of 5.

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20 Comments

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This looks like such a fun trip to Chicago! We did the same river cruise pre-kid and loved it. Definitely planning a trip to Chicago with my son in the near future!

Awesome! We loved it there! Hopefully you and your son can do some of these same things 🙂

What a fun trip to Chicago! I’ve had quite a few dog-friendly Chicago trips and we always have a great time. The Architectural River Cruise is a must! It’s such a wonderful way to view the amazing buildings.

I noticed that it was very dog-friendly! We love that about Duluth, MN too!

I would love to visit Chicago!

Yes, it is truly great! Let me know if you ever need additional tips!

As a (former) Chicago resident, I can honestly say this is a great itinerary! Portillo’s Chopped Salad is my favorite and I grab one anytime I’m passing through Phoenix as they actually have a couple of Portillo’s locations.

That is the best feedback ever! Thanks for sharing! I didn’t have that salad…but will have to when we go back!

I would love the opportunity to do more of Chicago. Navy Pier was a big highlight but i’d love to do some of this other stuff!

Yes, there is literally so much to see and do for all ages! We will definitely be returning soon!

We adore Chicago – saving this four our next trip!

Yay! This itinerary was flawless for us! Let me know if you return!

Chicago is one of my favourite cities in the USA, this post has got me desperate to return!

Basking in the memories, it makes me want to return too!

My brother isn’t that far from Chicago! We should make a weekend of visiting him and seeing the city. Thanks for all the tips!

For sure! You’ll love it! Plus, you’ll get to see your brother!

Saving this! We have one day in Chicago on our upcoming October trip with kids and I can’t wait! Thanks for the tips!!

Yay! So glad that you find is useful! Have so much fun there!

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A Complete Guide for a Chicago Road Trip

Packing for a road trip to Chicago is a great way to explore new destinations, scout new neighborhoods, soak in the breathtaking views, and create memorable experiences. 

If you're planning a road trip to Chicago, the Windy City, it's essential to be well-prepared to make the most of your adventure. 

Since I have lived in the area for 30 years, you can use this guide that I created to help you through the essential items to pack, tips for driving in Chicago, road safety tips, and more.  

So, fasten your seatbelts and get ready for an exciting journey!

Essentials Items for a Chicago Road Trip

Firstly, let's get the obvious items out of the way. Although they apply to just about any road trip, I think it’s important to keep this in mind for Chicago too.  

Comfortable Clothing: When starting your road trip, opt for comfortable clothes that are suitable for long hours of sitting. Choose breathable fabrics, such as cotton, and consider layering to adapt to changing temperatures during your road adventure.

Weather-appropriate Gear: Depending on the time of year, Chicago's weather can be unpredictable, so pack accordingly. In spring and fall, you will want to layer your clothing. Bring a light jacket or sweater, a raincoat or umbrella, and hats and gloves for colder seasons.

Snacks and Drinks: Keep yourself fueled during the drive with a variety of snacks like granola bars, fruits, nuts, and bottled water. During summer, bring a cooler for the road trip to stay hydrated and to store perishable items. It will also s ave you time and money so that you don't have to stop and spend extra dollars at pricey convenience stores. 

Navigation Tools: Ensure a smooth journey by bringing a GPS device or using a reliable navigation app on your smartphone. For your road trip, you could have a physical map or printed directions that serve as backup.

Entertainment Options: Long road trips can be tiresome, so pack entertainment options like books, podcasts, or audiobooks. Prepare playlists with your favorite music to keep the atmosphere lively. Also, pack some games and movies or have a list of engaging car games prepared for the little ones when traveling on a road trip. 

Roadside Emergency Kit: Prepare for unexpected situations by carrying a roadside kit. It's always wise to be prepared for any emergencies on the road. Put together a roadside emergency kit that includes a spare tire, jack, jumper cables, flashlight, first aid kit, basic tools, and a roadside assistance contact number. Additionally, consider adding a portable phone charger and extra batteries to stay connected.

Tips for Driving in Chicago

When it comes to driving in Chicago, there are a few things that people might not know. First and foremost, be prepared for the notorious traffic congestion, especially during peak hours.

Chicago has a public transportation system. I advise that you use it as much as possible because it will save you time and money especially during peak season while visiting the city.

Peak Traffic Hours

The morning peak hours going into Chicago are between 6 AM and 9 AM. The peak hours leaving Chicago are between 3 PM and 7 PM.

The evening hours extend just a bit because some like to visit happy hour events, so the peak period is a tad longer.

Anytime outside of these hours is generally OK for driving except for popular sports events like a Bulls or Bears game, a concert, or other city-hosted events like parades and large festivals.

Also, note that Chicago is a bustling city that does a lot of business, so you will have to contend with semi-trucks, delivery vans, and heavy-duty trucks.

Construction

There is a saying in Chicago that "There are two seasons of the year, winter and construction."

Plan your driving around the peak traffic hours and look for alternate routes via GPS. Even if you have extra time, don't take it for granted.

Delays during construction are inevitable (and frustrating when the traffic is reduced from 4 to 1 lane)! There may also be delays caused by unexpected accidents or slowdowns caused by emergency vehicles.

Parking is always a challenge in the city and it's very expensive and fees for parking violations are hefty. The best way to locate a garage is via SpotHero.com. You can find discounted fees for early arrivals (before 7 AM) but the hours you are allowed to stay for the discounted price is usually limited.

If you are staying in the downtown area and have a parking spot, I suggest you leave the car and use public transportation during your stay. Getting around Chicago is very easy, and you will save more money by avoiding the expense of additional parking.

If you do need to use a car, familiarize yourself with street parking regulations. There is rarely free street parking and just about every parking space downtown is metered. Look for the meter posts near the end of each block to pay for parking. The machines accept cash and credit cards.

When parking in neighborhoods, you will find that some require a permit or vehicle sticker. In winter, the lack of snow removal makes it difficult to find parking so residents will "reserve" spots with chairs, cones, or anything they can find. My advice is to avoid using these spots or you may risk retaliation.

Lastly, if driving in Chicago intimidates you, stay in the right-most lane or use the side streets. Avoid the road rage caused by speeding drivers who don't use good driving etiquette. Try not to block cars who are trying to cross the main road from alleys, parking lots, or turning lanes.

Keeping these lesser-known aspects in mind will help ensure a smoother and stress-free driving experience in the bustling streets of Chicago.

Road Trip Safety Tips

While embarking on a road trip to Chicago, it's crucial to prioritize safety. Read further for some essential safety tips to ensure a smooth and secure road trip.

Check Your Vehicle Condition

Before hitting the road, inspect your vehicle's tires, brakes, lights, and fluids. Ensure everything is in good working order and consider getting a professional mechanic to perform a thorough inspection.

Plan the Route

Plan your route in advance, considering traffic conditions and any road closures. Utilize GPS navigation or maps to avoid getting lost and save time.

Share Your Itinerary with Family and Friends

Inform a trusted friend or family member about your road trip itinerary. Provide them with details of your planned route, accommodation, and expected arrival times. This way, someone will be aware of your whereabouts. Looking for more to do? Revew some recommendations in our ultimate guide to Chicago .

Take Regular Breaks

Long drives can be tiring, so take regular breaks to stretch your legs, have a snack, and rest. Fatigue can impair your driving abilities, so it's essential to stay alert and well-rested.

Stay Alert and Avoid Distractions

Keep your focus on the road and avoid distractions such as texting, eating, or adjusting the radio while driving. Remember, safety should always be your top priority.

Follow Traffic Laws

Observe and follow all traffic laws and regulations, including speed limits, seatbelt usage, and traffic signals. Be mindful of other drivers and pedestrians to ensure everyone's safety on the road. When in doubt, review the rules of the road for Illinois .

Itineraries by Car: The Most Scenic Drives in Chicago

Once you've reached Chicago, there are several iconic attractions you shouldn't miss. Here are some must-see places that will make your road trip unforgettable.

Lake Shore Drive

Take a leisurely drive along Lake Shore Drive, which stretches along the beautiful shoreline of Lake Michigan. Enjoy stunning views of the lake, the city skyline, and iconic landmarks like Navy Pier and Grant Park.

Lake Shore Drive is about 16 miles long. You can start at 67th Street in the South Shore neighborhood and go north to Hollywood Avenue.

The Magnificent Mile

Cruise along North Michigan Avenue, known as the Magnificent Mile. Marvel at the impressive architecture, luxury boutiques, and iconic landmarks as you drive through this bustling shopping district.

The Magnificent Mile is one mile long and starts at the Chicago River and extends north to Oak Street Beach .

The Outer Drive

The Outer Drive is also known as South Lake Shore Drive. This scenic route takes you through the southern part of the city, offering picturesque views of the lake, harbors, and the Museum Campus which consists of The Field Museum, the Shedd Aquarium, and the Adler Planetarium.

The Outer Drive starts at East Jackson Drive and extends south to East 67th Street. It is in the southern part of Lake Shore Drive.

Green Bay Road

Head north of the city and take a drive on Green Bay Road. This road offers a scenic journey through the charming suburbs, lined with beautiful homes, parks, and quaint downtown areas.

Green Bay Road extends through the northern Chicago community and multiple northern suburbs including Evanston, Skokie, Wilmette, Winnetka, Glencoe, Highland Park, Lake Forest, Waukegan, and Zion. These are great towns to explore outside of Chicago during your road trip.

Sheridan Road

Embark on a drive along Sheridan Road, which runs parallel to Lake Michigan. This picturesque route takes you through charming neighborhoods, historic mansions, and scenic lakefront parks.

Sheridan Road extends through the northern Chicago community and multiple northern suburbs including Evanston, Wilmette, Kenilworth, Winnetka, Glencoe, Highland Park, Lake Bluff, Lake Forest, North Chicago, and Waukegan. You make want to include a visit to some of these towns during your Chicago road trip.

Chicago Skyway

Experience a unique perspective of the city by driving on the Chicago Skyway. This elevated toll road offers fantastic views of the downtown area and provides a smooth route to neighboring Indiana for

Experience a unique perspective of the city by driving on the Chicago Skyway. This elevated toll road offers fantastic views of the downtown area and provides a smooth route to the neighboring state of Indiana for a day drive.

Final Thoughts on a Chicago Road Trip

A road trip offers an incredible adventure filled with iconic Chicago attractions , delicious food, vibrant culture, and memorable experiences.

By packing essential items, following safety tips, and planning your itinerary, you can make the most of your journey.

Don't forget to create your Chicago road trip itinerary or read some of our recommendations for a perfect blend of vacation activities , iconic sights, cozy accommodations, and unique experiences.ar

Explore Millennium Park and Navy Pier, dive into the city's vibrant culture, and immerse yourself in art at the Art Institute of Chicago .

When it comes to accommodations, choose from downtown hotels for convenience or boutique options for a personalized touch. Experiencing one of the best neighborhoods in Chicago will also create a memorable stay.

Indulge in deep-dish pizza (don't forget to invite me), take an architecture boat tour , and catch a thrilling sports event. Chicago offers a road trip experience like no other, where every moment can be filled with excitement and discovery.

What is the driving distance from to Chicago?

The driving distance to Chicago varies depending on your starting point. Use a reliable navigation tool or map application to get the most accurate distance information.

Are there any tolls on the way to Chicago?

Yes, there are tolls on some highways leading to Chicago. Make sure to carry cash or have an electronic tolling device like an I-PASS or E-ZPass for seamless travel.

How many days should I plan for a Chicago road trip?

The ideal duration for a Chicago road trip depends on your interests and the attractions you want to explore. A minimum of 3-4 days is recommended to cover the major highlights, but extending your stay allows for a more immersive experience.

Can I find parking easily in downtown Chicago?

Parking in downtown Chicago can be challenging, especially during peak hours. It's advisable to research parking options in advance of your road trip and consider using public transportation or ride-sharing services to navigate the city.

What are some offbeat attractions in Chicago?

Apart from the popular landmarks, you can explore offbeat attractions like the Garfield Park Conservatory , the 360 Chicago Observation Deck, or take a street art tour in neighborhoods like Pilsen and Wicker Park.

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NASCAR Chicago Street Race 2024 (Chicago) | Grant Park

Get ready to rev your engines at the NASCAR Chicago Street Race, set to take place at Grant Park on July 6, 2024. This adrenaline-pumping event will feature top drivers competing on the streets of Chicago, promising an electrifying experience for all attendees. The venue, located at 707 E. Balbo, Chicago, IL, 60605, will be the epicenter of speed and excitement as fans gather to witness the thrill of high-speed racing. From roaring engines to screeching tires, this race is sure to keep you on the edge of your seat. Mark your calendars because tickets for the NASCAR Chicago Street Race will be available for purchase starting from February 8, 2024, at 16:43, until July 8, 2024, at 04:00. Don't miss your chance to be part of this heart-pounding spectacle right in the heart of the Windy City. Get ready to experience the thrill of NASCAR like never before at the Chicago Street Race!

Provided by Coolidge | Published Apr 25, 2024

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