cool places to visit in chicago

51 Best & Fun Things To Do In Chicago (Illinois)

By: Author Jerric Chong

Posted on Published: September 1, 2020  - Last updated: October 17, 2023

What comes to mind when you think about Chicago?

Is it the gleaming skyscrapers and metallic bridges and buildings?

Is it the museums, theaters, galleries and other places of high art?

Is it the deep-dish pizza with its sticky cheeses stretching between your fingers?

Chicago is all of these things and more.

It welcomes 57 million visitors per year, and they’re all looking for the best places to see within the city.

They don’t leave disappointed.

Here are just a few things to do in Chicago, Illinois.

They range from the fun to the fanciful, and they’re sure to give you great memories of the Windy City!

Table of Contents

1. Millennium Park

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You can’t visit Chicago without visiting Millennium Park .

Not only is it one of the most famous places in the city, but its events, activities and festivities put it among the most-visited tourist attractions in America.

It’s anchored by “Cloud Gate,” the bean-shaped metal sculpture that has come to define Chicago.

Beyond the bean, you might recognize its ice rink from countless wintertime Christmas movies, or you might be familiar with its gigantic, video-playing water fountain that’s always a hot spot for selfies.

Other features of the park include a theater, botanical garden, art gallery and bike station.

An outdoor pavilion hosts concerts and carnivals.

A winding pedestrian bridge connects everything together.

If you’re looking for the best things to do in Chicago, it doesn’t get more iconic than Millennium Park.

It’s the Chicago equivalent of Times Square.

You’ll want to visit it at least once just to say that you’ve been there.

Address:  201 E Randolph St, Chicago, IL 60602, United States

2. Riverwalk

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The Riverwalk is exactly what it sounds like: a pedestrian trail that stretches alongside the Chicago River.

It’s 1.25 miles, so it doesn’t require a punishing amount of exercise, but it’s long enough to offer a wide range of events and activities for visitors of all types.

Are you feeling peckish?

Grab a bite to eat at one of the many cafes, bistros, bakeries and restaurants that line the water.

Do you want to shop ’til you drop?

Stock up on souvenirs everywhere from luxury boutiques to kitschy street stalls.

Culture lovers will enjoy the museums and theaters.

Outdoor enthusiasts can rent a bike, hop aboard a kayak or take a self-pedaling boat tour.

Couples can stroll under the stars; families can picnic in grassy fields or on top of stone steps that overlook the water.

The Riverwalk is a must see destination in Chicago.

There’s so much potential for fun that it’s almost like a mini-city in its own right.

You could spend your entire vacation exploring this 1.25 mile, and you still wouldn’t hit everything!

Address:  Chicago Riverwalk, Chicago, IL 60601, United States

3. Willis Tower

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Formerly known as the Sears Tower, the Willis Tower is a staggering 1,729 feet at its tallest spire.

This used to be enough to claim the title of “tallest building in the world,” but the completion of other skyscrapers in Dubai and Tokyo has knocked it down the list.

Still, the Willis Tower is one of the crowning jewels of Chicago.

In addition to being a busy commercial space for television and radio, it also has several observation decks for tourists.

You’ll enjoy breathtaking aerial views of streets, sidewalks, lakes, bridges and clouds as you marvel at a horizon that stretches for miles.

The most well-known observation point is the Skydeck, a high-rising platform that has walls and floors made entirely of glass.

There’s also the Skydeck Ledge, a series of transparent boxes jutting out from the side of the building that will allow you to walk on air from dizzying heights.

It might not be the tallest skyscraper in the world anymore, but the Willis Tower is definitely the tallest in Chicago, and it might even be the tallest in Illinois.

It’s guaranteed to give you a swooping sensation in your stomach as you look out at the world from 110 stories high!

Address:  233 S Wacker Dr, Chicago, IL 60606, United States

4. North Avenue Beach

You might think of Chicago as a cold, windy place, and it’s true that it gets a lot of the snow that brews over Illinois every winter.

However, it isn’t winter all of the time.

A summer in Chicago can be one of the best that you ever have, especially when you hit the beaches!

North Avenue Beach isn’t the only place to get some sand and surf in Chicago, but it’s one of the best.

You can go swimming or boating; you can rent a bike, kayak, paddle board, jet ski or water tube; you can take a yoga class as the sun rises or play a volleyball game as the sun sets.

Indoor activities are also available at a massive beach house that’s designed like a blue-and-white ocean liner.

It covers more than 22,000 square feet, and when you’re not engaging in its many entertainments, it offers breathtaking views of the water.

Buy a hotdog on a stick and take a stroll down North Avenue Beach.

As one of Chicago’s best shorelines, it’ll always live up to the hype.

Address:  1600 N Lake Shore Dr, Chicago, IL 60613, United States

5. Taste of Chicago

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With more than three million visitors per year, the Taste of Chicago is the largest food festival in the world.

It’s an absolute smorgasbord of everything from sloppy street food to elegant, restaurant-quality dishes.

If you like getting your grub on, it should be at the top of your bucket list!

Admission is free, and the food is sold through a ticket system that allows for both sample- and full-sized purchases.

You can stuff your face with an entire pizza; you can explore different flavors of noodles, burgers, tacos, tamales, soups, pastries and ice cream bars.

One of the selling points of the Taste of Chicago is that it welcomes vendors from all around the globe, so you can enjoy everything from authentic egg rolls to crazy gelato cups on the same street.

There are other forms of entertainment, too.

While you’re munching your way through the stalls and trucks, you can also enjoy games, dances, outdoor concerts, live cooking demonstrations and bohemian art galleries.

One year even featured a silent disco!

Forget about the boundaries of Illinois or the United States.

The Taste of Chicago is a fun, multicultural food festival that will let your palate travel the world without actually leaving the city.

It’s a must do if you’ll be in Chicago over the summer.

Looking for more things to do in Illinois ? Why not check out some of the fun things to do in Springfield, IL ?

6. Lincoln Park Zoo

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The Lincoln Park Zoo is such a staple of Chicago that it’s sometimes called the “Chicago Zoo.”

The city doesn’t have its own, however, and it’s probably because the Lincoln Park Zoo is already doing such a great job.

For starters, it’s one of the oldest zoos on the continent.

It was built in 1868, and some of its original structures are still in use today.

There’s even an oak tree that predates the founding of Chicago itself!

It’s also home to one of the best animal menageries in the state.

You can watch lions prowling in the grass, rhinos snuffling in the mud, penguins waddling on the ice and monkeys lounging around hot springs.

If you’re adventurous enough, you can get close to the critters with special feeding and petting events overseen by the staff.

People from all over Illinois come to see the animals of Lincoln Park Zoo.

It’s a top 10 destination for the city of Chicago, so whether you’re interested in birds, bugs or bonobos, it should absolutely make your “must see” list.

Address:  2001 N Clark St, Chicago, IL 60614, United States

7. Art Institute of Chicago

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With a pair of heavy bronze lions flanking the front door, the Art Institute of Chicago is one of the most recognizable and culturally significant places to visit within the city.

It’s home to more than 300,000 paintings, portraits, sculptures, ceramics, fabrics, photos and textiles, and its artwork transverses the globe from Sao Paulo to Shanghai.

You’ll probably recognize a lot of the art hanging on the walls.

From Grant Wood’s American Gothic to Pablo Picasso’s The Old Guitarist, the museum has scored countless coups over the years.

They have works by Monet, Renoir, Pollock, Warhol, Matisse, van Gogh and many other classic names.

They also have exhibits and artifacts from cultures all over the world.

You can look at traditional, hand-stitched Japanese kimono from behind painted screens; you can marvel at the heavy metal weapons of European crusaders in 1000 AD.

You don’t have to be an art expert to enjoy the Art Institute of Chicago.

It offers so many things to see and do that you’re sure to find something that piques your interest within its fun-filled corridors.

Give it a visit if you’re looking for amazing vacation ideas in Chicago!

Address:  111 S Michigan Ave, Chicago, IL 60603, United States

8. Chicago History Museum

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If you’re interested in the trials and tribulations that forged Chicago, the Chicago History Museum is where you can learn everything that you need to know about the city.

Topics range from the Great Chicago Fire of 1871 to the building of Chicago’s first railroads in 1836.

Abraham Lincoln plays a prominent role in the political exhibits since he considered Chicago his headquarters for most of his life.

There are also displays dedicated to Prohibition, the Civil War, the Women’s Suffrage Movement and other major movements that touched Chicago.

The best thing about the museum is that it doesn’t just list names and dates on plaques.

It brings history to life with things like interactive videos, moving trains, simulated fires and children’s climbing structures that look like gigantic Chicago style hotdogs.

It’s fun, and that’s why it imparts its lessons so well.

The Chicago History Museum is a must visit while you’re in the city.

It’ll give you context for a lot of the museums and landmarks that you’ll see, and it’ll enrich your experience as you explore one of the most important destinations in Illinois.

Address:  1601 N Clark St, Chicago, IL 60614, United States

9. Bobby’s Bike Hike

Bobby’s Bike Hike

It’s hard to say whether Chicago is more famous for its pizzas or its hotdogs.

Fortunately, with Bobby’s Bike Hike , you don’t have to choose between them!

Bobby’s Bike Hike is a touring company that specializes in food-based travel.

Offering multiple routes throughout the city, they’ll allow you to sample some of the best eats that Chicago has to offer, and you can customize the way that you experience them.

Do you live for dessert?

The “Sweets and Spirits Dessert Walking Tour” is filled with truffles, cupcakes and candy-infused cocktails.

Do you want to burn some calories while you eat?

The “Bikes, Bites and Brews Tour” will put you on a nine-speed as you work your way through craft beers, sausage rolls, deep-dish pizzas and hotdogs with all of the fixings.

If you’re looking for touristy things to do in Chicago, a food tour is a great place to start.

Pick a route with Bobby’s Bike Hike and get to eating!

Address:  540 N Lake Shore Dr, Chicago, IL 60611, United States

10. Wabash Arts Corridor

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Created by students from Columbia College Chicago, the Wabash Arts Corridor was designed to take creativity out of the classroom and into the real world.

They had the freedom to create whatever they wanted, wherever they wanted, and the end result was an explosion of self-expression that transformed the neighborhood.

Art is everywhere in the Wabash Arts Corridor.

It’s painted on doors, walls, windows and archways; it’s built on brick and stone and marble; it climbs up staircases and sweeps down into the cracks and crevices of back alleys.

You can’t turn a corner without seeing a new mural or an old piece of graffiti.

It’s unlike anything else that you’ll witness in Chicago.

Another fun feature of the neighborhood is that its artwork is constantly changing.

People paint and re-paint all of the time.

Some of it’s deliberate sabotage from street taggers, but more often than not, it’s just artists finding new ways to express themselves on outdoor canvases.

The Wabash Arts Corridor is one of the most unique things to do in Chicago.

If you want to get off the beaten path and explore the hidden gems of the city, let your feet take you to this beautiful, transformative artwork that refuses to be covered for long.

Address:  635 S Wabash Ave, Chicago, IL 60605, United States

Exploring other areas of Illinois? Why not check out some of the things to do in Galena, IL ?

11. Wrigley Field

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You can’t talk about Chicago attractions without talking about Wrigley Field .

It’s one of the oldest stadiums in Illinois, and it’s remained largely unchanged from its early days, so it still has things like old-fashioned floodlights and hand-turned scoreboards with peeling paint.

It’s also known for its ivy-covered outfield wall that has consumed many fly balls in its time!

Another cool feature of the field is that it’s located in the middle of a residential neighborhood.

Locals often sit on their roofs to watch games.

They also allow visitors to park in their driveways since there’s no parking lot connected to the stadium.

As for its events, Wrigley Field has hosted baseball, football, soccer and hockey games, and it’s also offered a number of concerts.

You should check the schedule to see what’s in store during your trip.

If you’re wondering where to visit in Chicago to really live and breathe its traditions, you’ll want to make time for Wrigley Field.

From the battered red marquee on the front entrance to the peanuts and hotdogs sold in the concession stands, it offers a classic baseball experience that’s hard to find anywhere else in the modern world.

Address:  1060 W Addison St, Chicago, IL 60613, United States

12. Shedd Aquarium

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With more than 35,000 creatures, the Shedd Aquarium is one of the largest aquariums in Illinois.

Not only does it house all of the sharks and stingrays that you’d expect, but it also showcases birds, bugs, snakes, amphibians and other creatures related to the sea.

The exhibitions are mostly divided by theme.

For example, the “Wild Reef” recreates the colorful coral settings of the ocean, and “Amazon Rising” is a purposefully flooded walkthrough jungle that’s meant to evoke the topics.

Other notable features of the aquarium include a movie theater and an underwater virtual reality experience.

You can also register for tours, presentations, feeding events and animal encounters.

The coolest ones are always quick to sell out, so if you’re looking for fun things to do this weekend, make sure to book early!

Shedd Aquarium is easily one of the top sites in Chicago.

Even if you don’t consider yourself an animal person, it’ll make a convert out of you.

Address:  1200 S Lake Shore Dr, Chicago, IL 60605, United States

13. Chicago Lakefront Trail

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Winding through the city for 18.5 miles, the Chicago Lakefront Trail is one of the best ways to check out the sights and sounds of a natural Illinois landscape.

You’ll pass through well-tended parks and overgrown marshes; you’ll see beaches, hills, groves, sidewalks and pedestrian bridges.

Your eyes will always have new scenery to roam.

Potential activities include everything from jogging to unicycling.

If you like being on wheels, there are several skate parks where you can practice your ollies and kickflips.

There are also ample places to stop and smell the roses if you enjoy picnicking.

As for places of interest, you can veer off the trail at any number of stops.

It’s located near piers, museums, clock towers, athletic stadiums and more.

Plan your trip around the Chicago Lakefront Trail.

Not only can it provide plenty of fun on its own, but since there are countless tourist attractions located on and near the paths, you can use it as a sort of natural compass for your trip.

You’ll never get lost when the trail is right there!

Address: 540 N Lake Shore Dr, Chicago, IL 60611, United States

14. Centennial Wheel

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The year was 1893.

The man was George Ferris Jr.

He wanted to build a gigantic metal wheel for the World’s Fair in Chicago, and despite skeptical reactions from everyone around him, he rolled up his sleeves and went to work.

Today, the Centennial Wheel is one of the most iconic tourist attractions in Chicago, and Ferris wheels are a standard feature everywhere from boardwalks to amusement parks.

It wouldn’t be an exaggeration to say that this little piece of Chicago forever changed the world.

You can still ride the Centennial Wheel.

It’s been renovated with modern safety features and all of the fun, high-class amenities that you could want, including a VIP gondola with plush seats and a glass-bottomed floor.

It’ll make for a great date night or family outing.

Ultimately, however, you don’t have to climb aboard the Centennial Wheel to appreciate the role that it plays in history or the importance that it has to Chicago, Illinois.

It’s a remarkable piece of architecture no matter what.

Address:  600 E Grand Ave, Chicago, IL 60611, United States

15. Untouchable Tour

Untouchable Tours – Chicago’s Original Gangster Tour

Illinois might not seem like a hotbed of mob activity, but Chicago is the exception.

It was famous during the Prohibition era as the central headquarters for Al Capone, Bugs Moran, Baby Face Nelson and many other mafia legends who made names for themselves with everything from bootlegging to gunrunning.

Not surprisingly, you’ll find lots of “mob tours” in the city that are designed to satisfy curiosity about these famous figures.

However, the Untouchable Tour is the original tour, and it’s also one of the best.

Its tour guides will actually dress up in suits and take on the personas of 1920s and 1930s gangsters as they show you around.

You’ll visit the places where dirty business took place, and you’ll get to see the murder sites for mobsters who killed each other or were gunned down by the FBI.

You’ll even get to see the site of the bloody St. Valentine’s Day Massacre of 1929.

The blood has been cleaned up, of course, but the legacy remains.

The Untouchable Tour is a must do for your vacation.

Not only does it offer a fascinating look into the dark history of the city, but it’ll also familiarize you with the streets and sidewalks of downtown Chicago, and that’ll come in handy for the rest of your trip!

Address:  600 N Clark St, Chicago, IL 60654, United States

16. Museum of Science and Industry

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Covering more than 400,000 square feet, the Museum of Science and Industry is the largest science center in the entire Western hemisphere.

It offers a staggering amount of things to see and do, so whether you’re into astronomy or zoology, its A-to-Z activity roster is sure to keep you entertained in Chicago.

Are you fascinated by natural phenomenon?

Stand inside of a simulated tornado or learn about the Earth’s forces with Wimshurst machines and Foucault pendulums.

Are you a geek for transportation?

Marvel at the airplanes dangling from the ceiling, and be sure to take a tour of the real-life trains, rockets and WWII submarines on display.

Other exhibits include everything from mirror mazes filled with optical illusions to 3D walkthrough models of the human heart.

If it’s a topic related to science, it’s probably featured here.

Between its events, activities and collections, the Museum of Science and Industry is a coveted jewel for Illinois.

It puts the state on the map in terms of scientific scholarship.

Even more importantly, it’s a lot of fun!

Swing by for a visit if you’re looking for the best and most educational places to go in Chicago.

Address:  5700 S Lake Shore Dr, Chicago, IL 60637, United States

17. Woolly Mammoth Antiques and Oddities

Woolly Mammoth Antiques and Oddities

The tables are covered in skulls.

The shelves are stacked with things like human dentures and lamps made out of alligator heads.

The bottles and jars are filled with eggs, skins, animal fetuses and other grotesque knickknacks.

Welcome to Woolly Mammoth Antiques and Oddities !

Created by a couple who wanted to “make (themselves) more comfortable with dying,” this bizarre shop has become one of the top stops in Chicago for the morbid.

It’s focused on death, but in a weird way, it’s also a celebration of life.

What can make you feel more alive than looking at a stuffed and mounted squirrel?

Drop by Woolly Mammoth Antiques and Oddities if you’re looking for unique tourist places in Chicago.

It isn’t something that you’ll find in a travel guide, but its utterly bizarre collection will definitely give you a story or two for when you return home.

Address:  1513 W Foster Ave, Chicago, IL 60640, United States

18. Chicago Theatre

You already know what the Chicago Theatre looks like.

Even if you’ve never stepped foot in the city, you’ve seen its vintage-style “CHICAGO” marquee in all kinds of films, shows and postcards.

It’s so widely recognized that it’s considered the unofficial emblem of Chicago.

There’s more to this theater than its signage, however.

Built in 1921, it’s a historical landmark that boasts amazing architecture and lavish, old-fashioned furnishings.

Walking into its front hall is like walking backwards through history to a time of high art and culture.

The balconies are plush.

The ceilings have chandeliers and gilded murals.

There’s even an authentic Wurlitzer pipe organ; it’s one of the last of its kind in the country.

The theater is operational, too.

It still hosts plays, musicals, orchestras, magic shows and more.

Its stage has welcomed everyone from comedians to motivational speakers.

If you’re looking for the best attractions in downtown Chicago, the Chicago Theatre is a must visit.

The marquee alone is worth a pilgrimage, but even beyond that, it’s a grand venue that’s designed to entertain and impress.

Address:  175 N State St, Chicago, IL 60601, United States

19. Navy Pier

If you’ve been making a to do list for Chicago, you’ve probably listed a few of Navy Pier ‘s attractions already.

It extends into Lake Michigan like a sort of overgrown boardwalk, and it’s absolutely packed with shops, restaurants, galleries, museums, movie theaters and other popular places for locals and tourists alike.

There are rides, too.

Navy Pier has a very festive atmosphere where you can always hear the jingling of carousel music and the whir of tower drops and wave swingers.

It’s also the home of the Centennial Wheel, the world’s first Ferris wheel.

Other attractions range from crazy funhouse mazes to elegant botanical gardens.

There are always things to see, and you don’t even have to visit the main attractions; you could have a fun, fulfilling afternoon just by wandering around, eating street food, listening to buskers and watching people cavort on the water.

For sheer entertainment value, Navy Pier is one of the top things to do in Chicago.

You’ll probably wind up visiting it even if you don’t plan on it.

It’s that ubiquitous to the social scene of Chicago.

20. Adler Planetarium

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Made with a dark, heavy granite, the Adler Planetarium is visually striking both indoors and outdoors.

The first thing that you’ll notice is the dome.

It measures a whopping 69 feet across, and it’s an architectural wonder.

When you sit down for a film or projection, the experience is so larger-than-life that you’ll feel like you’re careening through the stars on a real space shuttle!

Speaking of space shuttles, the planetarium has those, too.

Their exhibits include everything from meteorite chunks to old-fashioned metal space capsules from forgotten NASA projects.

If you’re a geek for astronomy, you might also like their special events for stargazing and celestial viewing.

Feel free to ask about their ongoing projects as well.

They’re an active research and observation station, and they host all kinds of educational programs for kids, couples, families, tourists and general visitors.

Are you looking for the best things to do in Chicago, Illinois?

Make time for the Adler Planetarium.

If you’ll forgive the pun, it’s out of this world.

Address:  1300 S Lake Shore Dr, Chicago, IL 60605, United States

21. Morton Arboretum

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There’s so much rugged natural beauty in Illinois that it’s almost a shame to stay in Chicago where the greenery has been replaced by skyscrapers and shopping malls.

Fortunately, there are still a few places in the city where you can get some fresh air, including the Morton Arboretum .

Like its name suggests, the arboretum is devoted to trees.

You’ll find many beautiful species here, including ones that are native to Illinois.

However, there are other things and places to see, so don’t limit yourself to a walk around the oak groves and conifer exhibits.

If you like flowers, you can check out the gardens and floral specimen collections.

If you’re traveling with kids, you can let them burn off some energy with a “troll hunt.”

There are also countless tours, trails and trams to let you explore every bit of the beautiful scenery that the landscape has to offer.

The Morton Arboretum is one of the most exquisite places to visit in Chicago, so if you’re keen to get away from the noise and traffic for awhile, treat it like a hideaway spot from the rest of the world.

The trees are just the beginning!

Address:  4100 IL-53, Lisle, IL 60532, United States

22. Superdawg Drive-In

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The lights are yellow and turquoise.

The hotdogs are served with fries, malts and milkshakes.

The carhops come right up to your vehicle after you’ve placed your order in the intercom.

Welcome to the Superdawg Drive-In , one of the last retro dining establishments in Chicago!

Founded in 1948, the Superdawg Drive-In hasn’t changed a thing about its operation since it first opened its doors during the days of poodle skirts and bouncy ponytails.

It’s still run by the same family, and they still serve the same salty, gooey and finger-licking goodness in paper hotdog trays.

Its authenticity is one of the reasons why it’s such a fun destination.

It isn’t pretending to be vintage; it really is!

If you’re looking for unusual things to do in Chicago, consider going back in time with the Superdawg Drive-In.

It’ll serve quick and delicious eats while hitting you with a blast of nostalgia that’s just as strong as the chill from your chocolate sundae.

Address:  6363 N Milwaukee Ave, Chicago, IL 60646, United States

23. Garden of the Phoenix

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Illinois might not be the first place that comes to mind when you think of cherry blossoms, but at the Garden of the Phoenix , they’re an annual event.

This beautiful, peaceful garden has been transported right out of a Japanese painting and into the heart of Chicago.

Curved bridges will lead you across ponds and streams.

Bonsai trees will provide shade from the sun.

Flower fields will offer amazingly fragrant mixes of camillas, chrysanthemums and morning glories, and birds will sing sweet songs over the sounds of babbling brooks and rustling tree leaves.

You’re probably impatient to hear about the cherry blossoms.

It’s okay.

Thousands of visitors flock to Chicago from all over Illinois just to see them every spring.

Their lives are brief, so make sure to time your trip when they’re actually in season, but seeing them in person is just as amazing as you think.

If you’re looking for attractions that you can’t find anywhere else in the state of Illinois, consider the Garden of the Phoenix.

Its cherry blossoms are a rare and exotic treat, but its real appeal lies in its beauty, serenity and tranquility.

Once you’re here, you’ll never want to leave.

Address:  6300 S Cornell Ave, Chicago, IL 60637, United States

24. Shoreline Sightseeing

Shoreline Sightseeing

Shoreline Sightseeing is a tour guide company that will put you on a boat and glide you through all of Chicago’s top attractions.

Rather than wandering around with your nose pressed into a map, you can grab a beer, kick your feet up and enjoy the sights from the sea.

There are several different tours to choose from, including an architecture tour that will showcase the city’s most famous landmarks and a lake tour that will give you incredible photo ops from the water.

In the summer, there’s also a fireworks tour to take advantage of Chicago’s weekly psychokinetic displays.

Amenities include drinks, snacks and restrooms.

Some tours come with free tickets for water taxi rides.

You can choose specific departure windows if you’d like to see a sunrise or sunset over the water.

If you’re pondering where to go during your Chicago vacation, consider a tour with Shoreline Sightseeing.

It will ensure that you don’t miss any of the major points of interest of the city, and since there are always tour times available, you could be sailing with them as early as this weekend!

25. Chicago Children’s Museum

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There are three stories to the Chicago Children’s Museum , and each one offers fun, dynamic experiences for families who want to combine learning and playing.

The Tinkering Lab has tools for builders and engineers.

The Dinosaur Expedition has hidden fossils that need to be dug up by pint-sized paleontologists.

The Cloud Buster has climbing structures for children who are more monkey than human, and Play It Safe has simulated emergencies in a firehouse to teach important lessons to tiny, helmet-wearing heroes.

As you can see, there’s a lot of stuff to do for kids.

But don’t worry if you’re a little tall for some of the rides!

Adults can find plenty of ways to entertain themselves as well, especially with after-hours events and programs.

Are you looking for Chicago attractions without age requirements?

Do you want something that offers more substance for your kids than shopping malls and amusement parks?

Spend an afternoon at the Chicago Children’s Museum.

The little ones will have fun, and if you’re lucky, they might just learn something as well.

Address:  700 E Grand Ave, Chicago, IL 60611, United States

26. Lincoln Park

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It’s an understatement to say that Lincoln Park is popular.

Not only is it the most-visited park in the state of Illinois, but it’s one of the most-visited in the entire United States.

It comes second only to New York ‘s Central Park in terms of annual visitors.

What draws people to the park?

For starters, it’s jam-packed with attractions.

There are zoos, gardens, conservatories, museums, movie theaters, cultural centers and more.

You can partake in the usual touristy things like dining and shopping, or you can try something new by visiting an archery range or going horseback riding in the hills.

Lincoln Park is also one of the most beautiful places in the city.

If you need a break from the skyscrapers for awhile, this is where you’ll find willow trees, lily ponds and tulip gardens.

Long story short, Lincoln Park offers the best of both worlds.

If you want excitement, visit the zoo or the beach; if you want peace and quiet, take a leisurely stroll on a nature trail.

Its versatility is probably one of the reasons why it’s such a crazy popular place in Chicago!

Address: 2045 N Lincoln Park W, Chicago, IL 60614, United States

27. Chicago Cultural Center

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With elaborate stained glass windows set in high-arching domes, the Chicago Cultural Center stands out even in a city already filled with amazing architecture.

It’s so impressive that it’s the meeting place of choice for presidents, princes, diplomats and other forms of royalty and celebrity.

They just can’t resist the grand staircases and mother-of-pearl mosaics!

If the architecture isn’t enough to tempt you into a visit, consider its activities.

You can find all sorts of interesting things to do here.

On any given day, for example, you might find lectures, concerts, film screenings, dance lessons, art lessons or theater performances.

Did we mention that it’s free?

Your wallet can stay in your pocket the entire time.

As a public outreach center, they won’t charge you for any tours or shows.

If you’re thinking about what to do in Chicago on a budget, consider the Chicago Cultural Center.

It’ll transport you into a high-class world filled with tea ceremonies and calligraphy classes, but amazingly, the trip won’t cost you a dime.

It’ll be an absolute steal for folks traveling through Illinois!

Address:  78 E Washington St, Chicago, IL 60602, United States

28. Petrillo Music Shell

Petrillo Music Shell

With a capacity of 35,000 people, the Petrillo Music Shell is one of the largest amphitheaters in both the city of Chicago and the state of Illinois as a whole.

As you might expect, it hosts a lot of concerts.

Its stages have welcomed everyone from indie folk bands to massive pop stars.

However, it’s also a venue that’s been used for rallies, sports events, food festivals and other forms of entertainment.

Here’s a small sample of the events that are held at the Petrillo Music Shell every year:

– Lollapalooza – Taste of Chicago – Chicago Blues Festival – Chicago Gospel Music Festival

It’s also hosted actors, athletes, comedians, popes, orchestras and even the Dalai Lama!

Long story short, the Petrillo Music Shell is more than just an amphitheater.

It’s a gathering place for the community.

If you’re keen on visiting the major points of interest in Chicago, you won’t want to miss this one.

Address:  235 S Columbus Dr, Chicago, IL 60601, United States

29. Merchandise Mart

FiledIMAGE / Shutterstock

Designed to look like a warehouse, department store and skyscraper all rolled into one, Merchandise Mart boasts more than four million square feet of floor space.

It’s so large that it used to have its own zip code even though it was right in the middle of downtown Chicago!

It was mostly used for offices and businesses.

Today, Merchandise Mart is still a hub of commerce, but it’s also open to the public with shops, show rooms and services.

You can mail a letter; you can buy a bottle of wine; you can get your clothes dry cleaned.

This is a shopping center with all of the goodies that you could ever need, and a food court is available when you get hungry.

There’s a reason why the building is often called “a city within a city.”

Special events at the mart include art shows, trade fairs, book signings, fitness classes and more.

It’s another one of those tourist attractions where you’ll want to keep an eye on the itinerary since there’s always something new going on.

Merchandise Mart used to be the largest building in the world.

It’s lost that title in recent years, but it still dwarfs everything else in Chicago, Illinois.

It’s a site worth seeing!

Address:  222 W Merchandise Mart Plaza, Chicago, IL 60654, United States

30. Maggie Daley Park

Maggie Daley Park is one of the most fun things to do in Chicago.

It’s basically a gigantic, all-ages recreation area that resulted from the crazy visions of an architect who never said no to any idea.

As a result, the park offers a million different amenities in delightfully clashing ways.

There are lawns, gardens, harbors, playgrounds and picnic areas as far as the eye can see.

A winding “ribbon” is an ice skating path in the winter and a jogging and biking path in the summer.

There’s a place for rock climbing and a place for rollerblading.

You can play tennis on the tennis courts or golf on the golf courses.

Kids will love the sprawling playgrounds that include everything from multi-level towers and slides to jungle gyms with suspension bridges and tunnels.

Adults will enjoy the fun, unique attractions like the mirror maze or the upside-down forest.

Maggie Daley Park is one of the top destinations of Chicago, and since it’s open 365 days per year, there’s no reason not to check it out while you’re in town.

Just drop by whenever you’re ready.

Whether it’s next weekend or next year, the park will always be insane!

Address:  337 E Randolph St, Chicago, IL 60601, United States

31. Violet Hour

The Violet Hour

Open every night from 6 PM to 2 AM, the Violet Hour is one of the best destinations for barhoppers in Chicago.

It has a sleek, sophisticated air that makes it much nicer than some of the other dives of downtown, and with strict house rules that include proper attire and no cellphone use while on the premises, it will give you the thrill of exclusivity if you manage to make it inside.

The decor includes dim lights, heavy black curtains and smoothly-polished wood grain tables.

It’s vaguely inspired by the speakeasies of Prohibition-era Chicago, but don’t worry; there are no mobsters here.

The cocktails are both delicious and fanciful.

They have names like “Moonchild” and “Giving Life to Memory,” so they’re something to remember.

You can also order bite-sized plates from an award-winning chef.

Do you have plans tonight?

Do you want plans tonight?

Pencil in a trip to the Violet Hour.

It more than lives up to its name by providing after-hours fun for adults.

Address:  1520 N Damen Ave., Chicago, IL 60622, United States

32. Montrose Beach

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Montrose Beach is one of the hidden gems of Chicago.

It’s much less crowded than other, more centrally-located beaches, but if you’re willing to take a bit of a drive into northern Illinois, you’ll reap the rewards of a gorgeous landscape without a lot of tourists.

The water glitters in the sun. Sand dunes shift with the wind.

Several piers jut out over the lake if you want to soak your feet; otherwise, there are wading and swimming areas, or you can ride a bilk along the asphalt trail that follows the water.

There aren’t a lot of amenities, but that’s part of its charm.

It’s a quiet, serene destination where you can do your own thing without kids crying everywhere and vendors hawking sunglasses at you.

If you’re looking for undiscovered tourist spots in Chicago, you’ll definitely want to check out Montrose Beach.

It’s a chance to get away from the grind of the city and enjoy a sunrise over the water without worries, crowds or distractions.

Address: 4400 N. Lake Shore Dr, Chicago, IL 60613, United States

33. Four Lakes

Four Lakes Snowsports

Four Lakes is one of the most beautiful places in the US .

It’s a little outside of Chicago, but if you’re willing to take a short drive to Lisle, Illinois, you can enjoy the breathtaking sight of miles and miles of snow.

Popular activities include skiing, tubing and snowboarding.

It’s okay if you’re a complete beginner; they have staff members who will rent you the gear, teach you the basics and take you down the slopes.

If you’re confident enough to venture out on your own, you’re free to do your own thing.

The terrain ranges from gentle bunny hills to elaborate boxes and rails for jumps, flips and grinds, so you’ll have your pick of settings for wintertime fun.

Four Lakes is one of the best skiing destinations near Chicago.

The powder is always fresh; the air is always crisp and clean.

What are you waiting for?

Book some time on the slopes for this week!

Address:  5750 Lakeside Dr, Lisle, IL 60532, United States

34. Myopic Books

rafallg / flickr

Hailed as one of Chicago’s top destinations for bookworms and bibliophiles, Myopic Books isn’t like your usual Barnes and Noble.

For starters, it only sells used books.

Many of them are rare or obscure titles that you won’t find on mainstream shelves, and they range from vintage sci-fi and busty romance novels to historical textbooks and true crime thrillers.

It’s also quite cluttered.

The building has three stories, but since there are more than 80,000 books on site, it’s a place of crowded tables, crammed shelves and books spilling over from floor stacks.

Of course, this might sound like heaven to a book lover.

There’s something magical about getting lost in the cozy confines of a thrift shop bookstore.

The smell of old books alone can be enough to make you sigh dreamily!

Despite its shabby appearance, Myopic Books is a treasure trove for collectors and antiquarians.

It can also provide a fun way to kill some time if you’re just wandering around Chicago and wondering what to do with your afternoon.

Let yourself be transported into a Ghibli film by entering this picturesque little shop with its weird, wonderful books!

Address:  1564 N Milwaukee Ave, Chicago, IL 60622, United States

35. 900 North Michigan

Sorbis / Shutterstock

Shopping at 900 North Michigan is one of the coolest things to do in downtown Chicago.

Not only does it offer amazing views from its pillar-like towers, but since it’s all indoors, it’s perfect for a cold or rainy day.

Hundreds of retailers call it home.

Many of them are luxury shops or specialty boutiques that give the mall a classy, upscale vibe, but you can find plenty of discount stores as well.

A spa is located on one of the top floors.

Several restaurants take the place of traditional food courts.

There are also cafes, bookstores, fitness clubs and other recreational areas that can be a lot of fun.

Many people wonder what to do when it rains on their vacation.

Fortunately, there are places to go in Chicago where the weather isn’t an issue, and 900 North Michigan is one of them.

You’ll spend so much time exploring its shops, stalls and boutiques that the rain might even finish while you’re inside!

Address:  900 Michigan Ave, Chicago, IL 60611, United States

36. Soldier Field

Max Herman / Shutterstock

There’s nothing like the pounding of 66,000 feet to make the earth move during a football game or rock ‘n’ roll concert.

At Soldier Field , you can enjoy this energy to its fullest extent!

As Chicago’s biggest stadium, Soldier Field plays host to all of the city’s top events.

You can watch football, soccer, hockey or rugby; you can attend political rallies or monster truck shows; you can jam out to everyone from Bon Jovi to BTS.

There’s always something new on the schedule, and it’s always crazy.

If you like behind-the-scenes action, you can also arrange a tour of the stadium that includes a peek inside of the locker room, an envious trip around the VIP suite and an exploration of the main field and courtyard.

At Soldier Field, every football game is the Super Bowl.

Every concert is Woodstock.

You won’t find a better stadium experience anywhere, so if you’re looking for ear-ringing fun in Chicago, this is one of the best sites for it.

Address:  1410 Museum Campus Dr, Chicago, IL 60605, United States

37. Crystal Gardens

Growing beneath a glass atrium, the lush trees and flowers of the Crystal Gardens are like something out of a storybook.

They have deep, wild roots, but they’re neatly contained in symmetrical structures with natural light shining down on open, airy spaces.

The decor is mostly white, but the colors of the plants are vibrant pops in the palette.

They’re also dotted with sculptures, fairy lights, water fountains and other beautifully aesthetic decors.

It should come as no surprise to learn that many weddings are held at the Crystal Gardens.

It’s a popular rental space for fancy functions in Chicago.

You don’t have to get hitched to see the flowers, however.

The gardens are open to the public, and they’re conveniently located on Navy Pier if you’re visiting other tourist attractions in the area.

As a bonus, admission is free.

Visit the Crystal Gardens for a beautiful and breathtaking nature tour that just so happens to be indoors.

Rain or shine, you can enjoy their elegant floral displays.

You might even find yourself planning your future vows among the flowers!

38. Baha’i House of Worship

BorisVetshev / Shutterstock

You can be forgiven if you’ve never heard of Baha’i, an obscure but fascinating religion that came from the Middle East.

Despite its millions of practitioners, it only has a handful of temples and prayer houses around the globe.

The amazing thing is that Illinois has one.

In fact, Illinois has the oldest and largest one, and it’s the only of its kind in North America.

The architecture is magnificent.

A lace-patterned dome sits on top of nine pillars that come together to form its center.

Inside, there are painted murals and stained glass windows.

Outside, there are pools, gardens, fountains and other gentle and tranquil spaces.

The Baha’i House of Worship is one of the most unique Chicago attractions that you can put on your itinerary.

You don’t have to be religious to appreciate its beauty, history and serenity.

It’ll fill you with wonder whether you believe like the Baha’i or not, so it’s absolutely a place to visit while you’re in Illinois.

Address:  100 Linden Ave, Wilmette, IL 60091, United States

39. The Weiners Circle

ChicagoPhotographer / Shutterstock

Its location might be small, but this bright yellow hotdog stand packs a major punch.

There’s a reason why it’s one of the best places to visit in Chicago!

The main draw of Wieners Circle is its funky late-night atmosphere.

It stays open until 5 AM on the weekends, so it’s a popular destination for bar hoppers and club goers who want to satisfy a drunken craving for cheese fries.

It also draws a lot of insomniacs who don’t care about traditional mealtimes and love digging into hearty, Chicago style hotdogs at any time of day.

Another fun thing about Wieners Circle is that its staff and customers are encouraged to yell at each other.

Mutual insults are an everyday thing.

It’s all part of the experience.

You won’t want to take your kids to Weiners Circle, but if you’re wondering what to visit in Chicago after the lights go off, this is a place where the fun never stops.

Even more importantly, it’s a place where you can get d*mn good hotdogs!

Address:  2622 N Clark St, Chicago, IL 60614, United States

40. Sky Rink

As you might expect from a place nicknamed “The Windy City,” Chicago’s weather can be pretty cold.

It helps if you lean into the chill rather than away from it, and to do that, you’ll need to visit a place like the Sky Rink.

Located at the top of Peninsula Chicago , a luxury hotel, the Sky Rink is a small and intimate ice skating destination where you can twirl under fairy lights while surrounded by bright, twinkling Christmas trees.

You’ll feel like the main character of a holiday movie as you enjoy the picturesque setting.

It’s quite romantic, especially if you’re traveling or honeymooning with a special someone.

When you’re done on the ice, a chalet service will be waiting to take your order.

You can warm up with everything from mulled ciders to powdered pastries that are fresh out of the oven.

With its chic decor and impressive amenities, a trip to the Sky Rink is one of the most fun things to do in Chicago.

You don’t have to be a guest at the hotel.

You can book a ticket anywhere and anytime, so it doesn’t matter if you’re arriving in the city today, tomorrow or this weekend.

Your dreamy date night is a go!

Address:  108 E Superior St, Chicago, IL 60611, United States

41. Welles Park

Harold Angle / Shutterstock

If you’re looking for a quiet place to unwind, Welles Park can offer a respite from all of the lights, noises and crowds of Chicago.

It isn’t without amenities.

Its centerpiece is an ornate, wire-topped gazebo where bands can play outdoor concerts and community leaders can give rallying speeches.

Other features of the park include a swimming pool, fitness center, baseball field, football field and children’s playground.

The best thing about the park, however, is that you can ignore all of the attractions and simply enjoy it for the natural oasis that it is.

It’s a great place to escape the hustle and bustle of Chicago, so whether you’re looking for grassy fields for picnics or shaded tree groves for nature walks, you can find them here.

Don’t get us wrong. Chicago is amazing.

It’s just very, very busy, and there are times when you might need a breather.

Welles Park is where you can get it.

Many Chicago attractions are focused on glitz and glamor.

For a plainer, quieter sort of space, visit Welles Park.

It’ll soothe your frazzled nerves during a stressful vacation, and it’ll recharge your batteries for the rest of your time in the city.

Address:  2333 W Sunnyside Ave, Chicago, IL 60625, United States

42. Magnificent Mile

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Are you wondering what to do on a last-minute trip to Chicago?

Do you need attractions that are always open or ones that can be booked quickly and easily?

The Magnificent Mile is the answer to your prayers.

Framed by shops, restaurants, resorts, malls, landmarks and other places of interest, the Magnificent Mile runs through the heart of downtown Chicago, and it offers a wide variety of fun for both locals and tourists.

You could spend days just sightseeing with all of the towers and skyscrapers looming over you!

To truly experience Chicago, however, you’ll need to dive into its urban landscape.

The good news is that you’ll have plenty of options.

The Magnificent Mile is home to 460 stores, 275 restaurants and 51 hotels, and that’s just the traditional, commercial side of things.

There are even more spaces for things like gardens, museums, theaters, art galleries and historical statues.

The Magnificent Mile is one of the best things to do in Chicago, especially if you’re taking an unexpected trip without the benefits of pre-booked tickets and tours.

It has so many attractions that you can always find something that’s open.

Even if your trip is as early as this weekend, the “Mag Mile” won’t let you down!

Address: North Michigan Avenue, Chicago, IL 60611, United States

43. Medieval Times Dinner and Tournament

Medieval Times Dinner & Tournament

Located a few miles north of Chicago in Schaumburg, Illinois, this is an attraction that will require you to travel outside of the city limits, but it’s definitely worth it.

Where else can you enjoy stew in hollowed-out bread while you watch men in armor fight to the death atop white stallions?

Okay, they aren’t really fighting to the death.

They’re just fantastic actors.

But that’s the whole appeal of the Medieval Times Dinner and Tournament : It takes you right out of this world and into the pageantry and peasantry of 11th century Spain.

The knights will ride, joust, sword fight and perform amazing tests of courage and skill.

You’ll watch all of the action as you’re served a hearty four-course meal.

For authenticity’s sake, you won’t be given any utensils, so you might want to wear clothes that you don’t mind getting splattered with gravy or stained with ale.

If you’re looking for fun things to do in Chicago, consider the Medieval Times Dinner and Tournament.

You’ll need to take a bit of a drive to get there, but once you’re yelling yourself hoarse for knights engaging in hand-to-hand combat, you’ll be glad that you did.

Address:  2001 N Roselle Rd, Schaumburg, IL 60195, United States

44. Second City Chicago

The Second City

How long has it been since you’ve enjoyed a real, honest-to-God belly laugh?

If you can’t remember the last time that you cracked up, Second City Chicago can help.

It’s more than just a comedy club.

Second City has locations all across the country, and it’s launched so many careers that it’s basically a pipeline to Hollywood.

When you attend a show, you’re almost guaranteed a good time with up-and-coming talent.

To give you an idea of what might be in store for you, previous acts have included Bill Murray, Stephen Colbert, Tina Fey, Amy Poehler, Steve Carell and many, many more.

Second City Chicago is one of the most vibrant attractions of the downtown area.

If you’re wondering what to see in terms of shows, plays, musicals and comedy routines, this is a destination to put on your shortlist for sure.

Address:  1616 N Wells St, Chicago, IL 60614, United States

45. Chicago Pedway

EQRoy / Shutterstock

How do Chicago natives survive the harsh winter weather?

One of the reasons is the Pedway .

Officially known as a “pedestrian pathway system,” the Pedway is actually more of a sprawling underground network of halls, tunnels and corridors that connect different streets in Chicago.

You can enter and exit at various points to get back to the world above, but since lots of businesses have set up shop in the Pedway, it’s become a destination in its own right.

Stores are available for shopping.

Restaurants are available for dining.

Art exhibits are everywhere; one particular standout is a collection of elaborate stained glass windows.

There are above-ground locations for the Pedway, too.

They’re enclosed paths and footbridges that can lead you through the city without exposing you to the elements.

The Pedway is one of the coolest places to visit in Chicago.

It’s basically a subterranean city, so you can eat, drink, shop and explore in an entirely underground setting.

You don’t have to let Illinois weather define your vacation!

Address:  Chicago, IL 60606, United States

46. Poetry Foundation Library

Poetry Foundation Library

The Poetry Foundation Library is another attraction that you can’t find anywhere else in Illinois.

In fact, you’d be hard-pressed to find it anywhere else in the US.

There are only a handful of poetry libraries in the entire world, but the good news is that the Chicago version is one of the best.

More than 30,000 volumes have been collected over the years.

They contain everything from flowery sonnets to raunchy limericks, so they’re quite diverse.

They can be found in books, diaries, anthologies, newspapers, scholastic works and more.

You don’t have to spend all day hunched over a table, either.

In addition to their printed works, the library also offers listening booths for audio recordings.

Some poetry is recited by the very people who authored it!

One thing to note about the library is that it has limited hours.

It’s only open on weekdays from 11 AM to 4 PM, so it might not be an option for those with a strict itinerary in Chicago.

If you have the time, however, and if you can appreciate a beautiful haiku, you should check out the Poetry Foundation Library.

It’s a unique gem in Chicago, Illinois, so it’s worth a day trip.

Address:  61 W Superior St, Chicago, IL 60654, United States

47. Field Museum of Natural History

With millions of artifacts on display, the Field Museum is one of the largest natural history museums in the world, and it’s renowned for its research and public education efforts as well as its collections that are just plain cool.

Gigantic skeletons will show you the jaw-dropping sizes of dinosaurs and woolly mammoths.

The hall of gems will beckon you with wondrous colors and glittering edges.

Underground tours will show you the earth below; space films will take you out of your seat and into the sky.

Plants are displayed in glass houses. Meteorite pieces are tucked into slides.

Flowers are pressed and preserved; ancient texts are printed on scrolls and silk screens; cultural tokens date back thousands of years and then some.

Taxidermy animals include everything from extinct species to notable creatures like the man-eating lions of Tsavo.

If this sounds like a lot, you should know that it isn’t even a fraction of what the Field Museum has to offer.

It’s home to more than 24 million items in total!

There’s a reason why it always tops the list of Chicago attractions, so whether you’re into birds, bugs or black holes, this is the museum for you.

Address:  1400 S Lake Shore Dr, Chicago, IL 60605, United States

48. Six Flags Great America

Six Flags Great America

Thrill-seekers, this one is for you.

Six Flags Great America offers roller coasters, bungee jumps, water slides, tilt-a-whirls, plummets, racers, bumper cars and much, much more.

It’ll be the ultimate adrenaline rush for folks who are looking for high-octane fun in Chicago.

It should be noted that the amusement park isn’t quite within Chicago.

It’s located in Gurnee, Illinois, which is about an hour north of the city.

That said, you should definitely take advantage of being close to a Six Flags.

It’s one of the best places to travel for food, fun and festivities no matter where you are, so whether you’re looking to chomp on deep-fried candy bars or scream like a banshee on a ricochet ride, it’ll offer an amazing vacation experience.

Make time for a trip to Six Flags while you’re in Chicago.

Book early. Find a coupon for an all-day pass.

A little planning today can net you a big discount tomorrow!

Address:  1 Great America Parkway, Gurnee, IL 60031, United States

49. Chinatown

ben bryant / Shutterstock

Even if you’ve been to Chinatowns in other cities, you’ve never been to Chicago’s Chinatown .

It’s such a vibrant neighborhood that it puts others to shame.

For starters, it really is a neighborhood.

It has all of the shops and street food stalls that you’d expect from a Chinatown, but beyond the gimmicky, touristy areas, there are parks, schools, museums, libraries and other important touchstones for the local Chinese community.

It’s also quite large.

With a population of almost 100,000 throughout the greater Chicago region, it’s easily the biggest Chinatown in the state of Illinois.

As for its attractions, you can drink, dine and shop to your heart’s content.

The food is usually the biggest draw for tourists, but if you’re interested in things like plays, market events and gallery openings, you’ll find plenty of those as well.

A trip to Chinatown is one of the best experiences that you can have in Chicago.

Grab your chopsticks and get going!

A steaming platter of red bean buns is waiting for you!

Address: 318 W Cermak Rd, Chicago, IL 60616, United States

50. Chicago Mosaic School

Chicago Mosaic School

If you’re hoping to have unique experiences in Chicago, have you considered learning a new skill or hobby while you’re there?

The Chicago Mosaic School is the only one of its kind in Illinois.

Originally just a workshop offered by a local ceramicist, it’s grown into an award-winning institution that’s dedicated to the preservation of the trade and the celebration of fun, creative artwork.

You can sign up for a number of classes and programs at the school.

If you already know your way around tiles, you can also test your expertise with the only mosaic certification program in the US.

If you just want to take a tour, that can be arranged, too.

The school has lots of its handiwork displayed in galleries, exhibitions, studios and showrooms.

Try something a little different during your vacation with the Chicago Mosaic School.

Whether you’re interested in expressing your own artistic side or just marveling at the creativity and imagination of others, this school is a unique travel destination in Chicago.

Address:  1127 W Granville Ave, Chicago, IL 60660, United States

51. Grant Park

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Grant Park is such a famous destination in Chicago that you might be surprised to find it at the bottom of this list.

The reason is because it’s a massive, multipurpose space that branches off into a thousand different directions with a thousand different attractions, so if you missed any of Chicago’s greatest hits, you’ll have one last chance to visit them before your vacation is over.

Did you check out the metal bean at Millennium Park?

Did you take a selfie at Buckingham Fountain or stroll through the Lurie Garden?

Did you get a little culture at the Art Institute of Chicago, or did you rock with an outdoor concert at the Petrillo Music Shell?

All of these destinations are on or near Grant Park.

There are countless others as well.

Grant Park is known as “Chicago’s front yard,” and once you’re standing at the entrance and seeing the entire buffet of cool things to do, you’ll realize why it earned the nickname.

If it isn’t one of the first places that you visit, make it one of the last.

Start Planning Your Trip To Chicago

These are just a few of the best places to visit in Chicago, Illinois.

Whether you’re looking for refined art or bizarre street food, it’s a city that has a little bit of everything, so it’ll be an excellent destination for your travel bucket list!

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Home » North America » Chicago

31 Best Things to Do in Chicago – Itineraries, Activities & Daytrips

Chicago is an incredible destination. Called the Windy City (but not actually that) windy), Chicago sits on the shores of Lake Michigan and boasts a truly picturesque skyline.

It’s not seeing the modern skyscrapers that make up a million  things to do in Chicago  for the regular tourist though; tales of Prohibition-era crime and gangsters of yore provide an interesting historical backdrop for the city. Combine this with famous Chicago deep-dish pizza, and you can see why millions of people visit the city each year.

Thankfully there’s plenty of opportunities to get off the tourist trail in Chicago. To help you navigate your way around the more weird and wonderful sights of the city, we’ve crafted this guide to the most  unusual things to do in Chicago . From secret magic shows, to hidden speakeasies and surgery museums, we’ve got all the hot tips you could ever need!

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Top Things to Do in Chicago

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Are you visiting Chicago ? Chicago is a hub of entertainment, fun attractions, and iconic sites. Here are some of the best things to do in Chicago on any budget, whatever the weather.

1. See the city from the top of the Willis Tower

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Once known as the Sears Tower, the Willis Tower looks no less cool after its 2009 name change. Sleek black and a bit like something you’d make out of Lego as a kid, it not only looks cool: the views from it are insane . They’re bound to be. We mean, the observation deck of the Willis Tower is the 103rd floor. 103rd! From this unreal viewpoint you can see over fifty  miles and out across four states .

For those of you who don’t get wobbly knees and vertigo, there’s The Ledge. This is a glass platform that literally sticks out of the tower itself. Standing on it, you can see the street between your feet – 412 metres below. Definitely one of the most iconic things to do in Chicago ( and worth it for the photo op ).

2. Pose for a selfie with the Cloud Gate

Though it’s got a cool sci-fi name, Cloud Gate is known by basically anyone who’s anyone as The Bean. That’s what it looks like: if the Silver Surfer was a bean, this would be it. And even just going to see it is one of Chicago’s most essential things to do. Designed by British artist Anish Kapoor, The Bean is located as Millennium Park.

A selfie in the weird reflections of this very cool piece of public art itself is a must. Come early for less chance of having a random in your shot (unless you like random crowds?)

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!

3. Discover the (many, many) tastes of Chicago’s Chinatown

A load of different cultures have added to what makes Chicago so god-damn cool and Chinese culture, of course, is a big part of it. Like all good, big American cities worth their salt, Chicago has its very own Chinatown. And what better way to discover how it ticks than to embark on a voyage of food and feasting through this buzzing district.

Step through the iconic Chinatown gate and immediately start your quest for the best. Dig in to dim sum, dine on dumplings, and try delights from Xi’an you’ve probably never had before. Beijing duck, Sichuan hot-pot – it’s all here. For one of the very best things to do in Chicago, make sure you finish up with a custard tart from Chiu Quon Bakery, Chinatown’s oldest.

There are so many amazing food tours in Chicago that’ll show you the best spots to eat.

Downtown/The Loop is undoubtedly the most famous and the best area to stay in Chicago. Home to the city’s business district, this area of Chicago is packed with skyscrapers, lively theatres, and picturesque architectural landmarks.

• Take a picture at Cloud Gate, the iconic Bean sculpture
• Tease your taste buds with a giant sandwich at Eleven City Diner
• Enjoy great cocktails and delicious food at BIG Bar

4. Delve into the history of the city

Chicago wasn’t always a big, shiny metropolis. Not at all. Rollback the years to as recently as the 19th century and Chicago was pretty much just a pioneer outpost, and an important stop-off for trappers and fur trade buyers. What happened between then and now? We won’t bore you with it, because it’s much  more interesting to learn about it first hand at the fascinating Chicago History Museum.

This ain’t no dull and dusty prison of artefacts. What you get here is a lot of hands on, interactive exhibits that makes history fun! Step inside a recreated old jazz club , a restored L train car (iconic), and clap eyes on a giant, Chicago-style hot dog. A super interesting thing to do in Chicago – even if you’re no history buff yourself.

5. Take in the sights and sounds of the Navy Pier

What’s Navy Pier you ask? Well, it’s a 3,300-foot long pier on the shore of Lake Michigan that isn’t just famous for being long – it’s also got some heritage to it, dating back as it does to 1916. That’s over a century old (wow, right?). Seeing it alone doesn’t constitute the best thing to do in Chicago: this pier is an experience .

It must be walked around. There are tons of attractions on  the pier itself, everything from old-time-y fast food stands and shops, to exhibitions, seasonal festivals and even stunning views out across the lake. Sounds good, doesn’t it? Which is probably why it’s one of the most popular things to do in Chicago.

6. Unearth Chicago’s criminal past

Chicago isn’t just famous for its pizza (we mean, we’ve already told you five other awesome things). It’s also famous for crime. But before we start getting hate, we’re talking  historic  crime. Think the Chicago Mob, Bugs Moran, Frank “The Enforcer” Nitti, The Lady in Red, The Untouchables, Johnny Torrio, John Dillinger and – of course – the famous, the notorious, Al Capone.

So for one of the coolest things to do in Chicago, go on your very own stake-out and check out places where all these hoodlums gathered. Search out spots like the Holy Name Cathedral, the Biograph Theatre, and the site of the Valentine’s Day Massacre in Lincoln Park. Nothing quite like a bit of Prohibition-era gang warfare.

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7. Dig into Chicago Style Pizza

From the North to South Side of Chicago, there’s one tasty dish that you won’t be able to get away from. It’s going to happen sooner or later. But don’t worry: this is one tasty morsel that you will definitely  want to fill your tummy with. We’re talking, obviously, Chicago deep-dish pizza.

An unholy cross-breed of a pie and a pizza, maybe even a casserole encased in chewy dough, it’s a must-have for stuff to do in Chicago. For the best place to start your pizza odyssey in Chicago, start at strip mall favourite: the succulent My Pi Pizza. Then there’s Burt’s Place for a timeless taste. For old-school style, make a beeline for Louisa’s Pizza and Pasta .

• Where To Stay in Chicago
• Hostels in Chicago Guide
• Best Airbnbs in Chicago

8. Hunt for bargains at the Randolph Street Market

If you’re into a bit of vintage clothing and other knick-knacks and relics from the past, going for a bargain hunt at Randolph Street Market is definitely one of the top things to do in Chicago. No doubt about it. This mecca of cool has been featured in stuff like the New York Times and Travel & Leisure, so you  know  it’s a hip place.

This monthly indoor-outdoor market is a bonanza of things to buy and places to eat as well. It’s located in Chicago’s Plumbers Hall and takes place over one weekend every month. It’s ticketed though; general admission is $8. But boy is it ever worth it. Hot tip: Come after 3pm on a Sunday for free admission.

9. Get up close and personal with the Crown Fountain

Probably one of the more unusual fountains in the world, the Crown Fountain – for a start – is a pair  50-foot tall cuboid block of glass bricks with a shallow reflection pool between them. That alone makes it a striking piece of public art. We say striking, but back before it was unveiled in 2004 it was downright controversial.

But the best part about the fountain isn’t the architecture. It’s the LED projections of over a thousand Chicago locals from different backgrounds and walks of life, making it look like they’re spewing water at you from their mouths – sort of like a modern-day gargoyle. Seeing it (without getting wet) is the one of the coolest things to do in Chicago.

10. Spend the afternoon strolling around the Chicago Institute of Art

For one of the less tourist-y things to do in Chicago you should definitely check out the Chicago Institute of Art. This place really does have quite an insane collection. You’ll get to a few of the greatest hits of some of the most famous artists that ever lived.

We’re talking “The Bedroom” by Van Gogh, Edward Hopper’s cafe landscape “Nighthawks”, “A Sunday on la Grande Jatte” by pointillist Georges Seurat, and the very iconic “American Gothic” by Grant Wood. That’s just a few. There’s stuff by Diego Rivera, Mattise, Monet, even Hokusai. Art fans should not pass up on this incredible haul.

11. Spend a day hitting up the city’s donut joints

Donut miss out (sorry, that was awful) on sampling Chicago’s delicious donuts. It  must  be done – especially if you’re at all fond of these deep-fried rings of goodness. Dunked in coffee, old fashioned style, whatever you go for it’s bound to be literally delicious. We kid not.

With a recent resurgence in the popularity of donuts in the city, believe it or not, there’s a few good’uns to discover if you’re in the search of off the beaten track stuff to do in Chicago, like donut-hunting. Hit up Dinkel’s Bakery . Going strong for over 90 years (try the chocolate-coated). Over at Delightful Pastries, this family-owned operation has paczki – jam-filled donuts of Polish origin. Unreal.

12. Pay a visit to the actually beautiful International Museum of Surgical Science

A trip International Museum of Surgical Science may be of the more unusual things to do in Chicago, but it’s actually a pretty fascinating (if gory) place. It’s filled with strange things like preserved heart valves in jars and graphic depictions of surgery from back in the day – well, actually 600 historic paintings – so if you’re squeamish… look away.

Luckily for the less strong of stomach, the museum is set in a lakefront, early 20th-century mansion. It’s stunning. Think wood panelling and leather chairs, marble floors and gilded staircases. It’s worth a visit for the building alone. At the end you can even pick up kooky souvenirs from the gift shop. Plushie microbe, anyone?

13. Visit the birthplace of Ernest Hemingway

Just west of Downtown Chicago is the leafy, and fairly fancy, suburb of Oak Park. It’s here that on 21st July, 1899 – on the second floor of a Queen Anne-style home – that Ernest Hemingway was born. Without doubt one of the most iconic (if not greatest) American writers, Hemingway spent the first 6 years of his life here.

One of the more unique things to do in Chicago – but a must if you’re a Hemingway fan – you can join a tour of his beautifully restored birthplace once every hour. It takes about 45 minutes and includes various facts about the early life of the young, future Pulitzer and Nobel Prize-winning Hemingway.

Safety in Chicago

Despite having a reputation as a major centre of crime, it’s a pretty safe city. Yes, there was all that Prohibition-era stuff, but that was 100 years ago and as a tourist you’re going to be fine here. The modern crime in Chicago is an issue for the city but happens in more isolated areas far from the central sights and lights of the city. In shorts, Chicago is safe for tourists .

There are, of course, some rougher areas that you might want to consider avoiding at night. The Fuller Park area as well as the far West Side (after West Avenue) aren’t the nicest places to wander.

All that said, you should be wary of your belongings in  all  areas of Chicago – especially the subway. And after all the suits and office workers have gone home, the centre can harbour some pretty aggressive begging.

Use your common sense, stick to well lit roads, don’t wander down deserted alleyways, and you should be fine!

Read our tips for traveling safely before you fly and always get travel insurance. Check out our roundup of the best travel insurance .

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…)

14. Be amazed by the night sky at the Adler Planetarium

By now you’re probably aware that Chicago has some pretty cool slices of history to learn about. Another one of these is the Adler Planetarium – the first in America. We think that’s pretty cool. And yes: the building itself is also pretty cool. But the coolest thing? It’s a planetarium, people!

We’re into it. For a more romantic thing to do in Chicago at night, the adults-only Adler After Dark happens on every third Thursday of the month (6-10pm). See the stars from the Doane Observatory, see a bit of live music, and grab a cocktail. Planetariums don’t get better than that!

15. Spend a night with the bluest people around

The classic that is Blue Man Group has just a few homes across the US – and Chicago is one them. One of the best things to do in Chicago at night would be to book yourself a ticket and grab a seat for one of the weirder theatrical performances you’re likely to see in your life. For starters, everyone is blue.

It’s a multimedia extravaganza that started as a “creative disturbance” put on by three friends in the Lower East Side of Manhattan when they put on a tiny parade, which involved burning a Rambo doll and a piece of the Berlin Wall. That strangeness persists. Be warned: front row seats are in a “splash zone”.

16. Have a drink at a Chicago speakeasy

With Al Capone and other gangsters running the show in Chicago during the Prohibition, alcohol still flowed freely – albeit in an underground way. Behind-closed-doors clubs that were known as speakeasies came into life, serving illicit alcohol to those who couldn’t do without it, i.e. almost everyone.

The Violet Hour is a good way to relive that era of tommyguns and moonshine liquor – except this time with fancy cocktails. A bit of a hidden gem, especially if you’re into hipster vibes and all that jazz (literally), having a few drinks here is a great thing to do in Chicago at night.

Looking for a specific place to stay? These are our highest recommendations for the best places to stay in Chicago.

Best Hostel in Chicago:  Freehand Chicago

Set in stunning Streeterville is Freehand Chicago – our pick for the best hostel in Chicago. This charming hostel is built in a classic 1920’s building and comes complete with stylish décor. It has a cocktail bar, a fitness centre, and on-site laundry facilities. They even provide linens, blankets and plush towels to guests.

Best Airbnb in Chicago:  The Spartan

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 Hotel in Chicago: Fieldhouse Jones

Cool and comfortable, stylish, and rustic; these are just a few of the reasons Fieldhouse Jones is our favourite hotel in Chicago. Not only is this hotel close to transit lines, but there are plenty of bars, clubs and pubs nearby. It has comfortable rooms, clean facilities and a friendly staff.

17. Ride a huge ferris wheel together

If the Willis Tower seems a little bit too high for you (to be fair, it’s pretty damn tall), then you can always opt for a ferris wheel. Because of the close quarters nature of ferris wheels, they automatically win for the romance factor. Even more if you go for a ride at night time.

The Centennial Wheel, built for the 100 year anniversary of Navy Pier, is one of the most romantic things to do. The glittering views across the lit-up city skyline is literally stunning. Nothing like an amazing city view at night for a perfect little date night. Hot tip: Save your precious time for a fancy dinner afterwards and book tickets in advance to skip the queue.

18. Spend the day at Oak Street Beach

Who knew that Chicago had beaches? Well, it does. Being on Lake Michigan , you probably knew it at least has a shoreline, but beaches? So if you’re looking for romantic things to do in Chicago, pack up a picnic, your best swimmers, and some blankets and make your way to the surprising slice of sand that is Oak Street Beach.

Fairly long and spacious enough for everyone to find a spot, there’s even a biking path along the green park behind the beach. And it’s backed by an impressive bank of skyscrapers. Pretty cool. Even on a winter’s day it’s nice for a romantic stroll together, but we would say that it’s probably more something to do in Chicago in summer. Don’t forget sunscreen!

19. Follow the Yellow Brick Road to Oz Park

In the North Side of the city you’ll find a pretty unusual thing to do in Chicago. Namely, it’s a park dedicated to all things Wizard of Oz. There’s Dorothy’s Playlot, the community-based Emerald Garden, and statues of the Tin Man, the Cowardly Lion, the Scarecrow, Dorothy and Toto. Before you get your hopes up, there is no Yellow Brick Road.

You’re probably wondering: Why? Good question. It all started because of one the area’s more famous former residents: L. Frank Baum . A Chicago-native who lived in the Lincoln Park area in the 1890s, he was the author of the original The Wonderful Wizard of Oz . In his honour the city transformed this once run-down area into the space it is today.

20. Take a break next to one of the biggest fountains in the world

Pretty much nothing like the modern monoliths that make up the Crown Fountain, the Buckingham Fountain dates back to 1927 and is designed to look like a Rococo wedding cake. If you’re wondering what that looks like, think ornate in a monumental way. Supposedly built to represent Lake Michigan itself, this tiered fountain boasts statues galore.

In operation from 8am to 11pm the fountain’s jets shoot up 150 feet into the air, which is genuinely impressive to see. At night time, these become a choreographed marvel complete with music and lights. For free things to do in Chicago, coming to see this  huge  fountain is up there.

21. Stroll the Chicago Pedway

We cannot help but love the futuristic feel of a city that connects buildings to other buildings with underground tunnels and overhead bridge links. There’s something amazing about it. Like, you know, the city of tomorrow or something. If you’re like us, then you’ll agree that exploring the Chicago Pedway is one the best things to do in Chicago.

First began in 1951 when several one-block tunnels linked the Red and Blue CTA lines, today it spans 5 miles and connects over 50 public and private buildings and CTA stations. Dotted throughout are a whole load of services from restaurants and bars to shoe repair shops. Not it’s not just about keeping warm, but Chicago really does get super cold in winter.

Books to Read in Chicago

Sometimes a Great Notion – A tale of a hardheaded Oregonian logging family that goes on strike, leading the town to drama and tragedy. Written by PNW legend, Ken Kesey.

Walden – The transcendental masterpiece by Henry David Thoreau that helped modern Americans rediscover nature and her beauty.

To Have and To Have Not – A family man gets involved with the drug smuggling business in the Key West and ends up in a strange affair. Written by the great Ernest Hemingway.

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23. All aboard the river boat to see the city

You’ve seen the city from up high. You’ve seen it from ground-level. You’ve even seen it from below (that Pedway is awesome). But a good way to see the city is from the Chicago River. And what child wouldn’t completely lose their sh*t over a boat ride? Not many, that’s for sure.

Catch a boat from near the DuSable Bridge along the Riverwalk on the south bank of the Chicago River and you’ll whisked upriver, through a very cool lock system all the way to Lake Michigan, before being lowered back into the river itself. The level of engineering excitement and watery appeal of it is enough to make this a top thing to do in Chicago with kids.

For an even more memorable trip, you should consider renting a boat in Chicago , which will take you anywhere you want to go on the river or Lake Michigan for an affordable price.

24. Have fun playing and learning at Chicago’s Children’s Museum

It’s in the name: the Children’s Museum is all about learning and having fun whilst you’re doing it. If you’re stuck for things to do in Chicago with kids and you’re really strapped for ideas, this one is a total no-brainer. It’s actually super cool and will keep your children (and you) entertained for actual hours.

There’s permanent exhibits like the Tinkering Lab – for older kids (drills and hammers at work here!) – whereas younger children will love digging for bones at the Dinosaur Exhibition; elsewhere Treehouse Trails and Kids Town are ideal for babies and toddlers. There’s always something new here. Tip: it’s a good thing to do in Chicago when it’s raining because it’s indoors!

24. Try To Escape From The Escape Game!

If you are after something challenging, immersive but totally then then the Chicago Escape Game may be just what you are looking for. The Escape Game features a variety of different rooms which participants (that’s you and your crew) must try to escape from by working as a team, solving clues and completing puzzles.

All of their games are designed to be suitable for everybody, from first-time players to experienced escapologists. No matter which one you decide to play, you’re sure to have an absolute blast!

25. Get your Grand Designs on at Farnsworth House

Chicago has no shortage of amazing buildings, but most of them are either skyscrapers or old-time-y structures. Thankfully there is one particular building, namely the Farnsworth House, which is definitely worth your time. And if you’re into design, you’re going to freak out at this place.

Designed in 1951 by Mies van der Rohe – the founder (and leader) of the Modernist movement in Europe who spent 30 years living and working in Chicago – this thing is super cool. This guy basically pioneered glass and steel architecture and you can see it in his house. Visiting it should be a must if you’re on the look-out for hip things to do in Chicago. Instagram fodder if we ever saw it.

25. Stroll around Garfield Park Conservatory

There’s a lot of… city in Chicago. A lot of buildings. A lot of skyscrapers. All those tall, tall manmade structures might get to you after a while – especially if you’re not from a city. So if you need some space, the Garfield Park Conservatory is the place for you.

One of the last conservatories in the US – often called “landscape art under glass” –  this place is bursting with greenery and tropical plants. If you love your succulents and your Instagram gallery is full of artsy pics of houseplants, we urge you to go here. Case in point: there’s a Palm Room, with a zillion varieties of palm. One of our favourite hipster things to do in Chicago.

26. Get your kicks from magic tricks at Chicago Magic Lounge

Yeah, we know that magic shows don’t really have the coolest reputation but hear us out on this one. The Chicago Magic Lounge is a pretty funky little venue where you might just be spellbound like you’re a kid at a birthday party again. Even getting inside this place is like some sort of trick or inside joke as guests enter through what appears to be an old-school laundromat.

Step through the portal in to this world of magic, and spend your evening enjoying some pretty tasty cocktails whilst being suitably impressed, wowed and confused by what the hell is going on and how these tricksters do it.

27. Uncover the Mexican culture of Chicago

Just a 15 minute train ride from central Chicago is Pilsen. With its murals popping with colour, Spanish signs and plentiful Mexican cuisine on offer, it honestly feels more like you’re in Mexico than in the city limits of Chicago. You’ll even find the National Museum of Mexican Art here.

So if you’re looking for off the beaten track things to do in Chicago, then we would highly recommend a trip to Pilsen. Forbes recently named it as “one of the coolest Mexican neighbourhoods in the world.” (Um, what about in Mexico?) Seriously though, it really is cool here.

28. Catch a game at Wrigley Field Ballpark

Calling all sports fans! Wrigley Field Ballpark is totally worth a visit. You’ll find it in the North Side of the city. Getting a ticket for a game is easy enough. Turn up to the ticket window and pay. See – we said it was easy.

The ballpark itself is the second-oldest in the United States, having been built in 1914 and pipped to the post by Boston’s Fenway Park (1912). Catching a game here is one of the best things to do in Chicago. Loads of other people think so too: it’s been featured in loads of stuff from The Simpsons  and Family Guy to  Ferris Bueller’s Day Off .

29. Soak up the sights and sounds of the city on a bike

If those feet of yours are tired of pounding the pavements around the Windy City, if distances seem too long to walk, if navigating the Pedway system or traffic seems too much hassle, then boy have we got the solution for you. You can see it all on two wheels instead.

Hop on a bike and pedal along the 18-mile Lakefront Trail that snakes along the shore of Lake Michigan, from Grant Park to Lincoln Park. It’s ideal for cycling, obviously. One of the better things to do in Chicago for keen cyclists especially, seeing the city from the relative comfort of a bike saddle is a chilled way to do it. Rent a bike from one of many stations along the trail itself.

30. Go for lunch at Fulton Market

The industrial neighbourhood of Fulton has had bit of a facelift in recent years. From way back in the rough and ready days of its meat-packing past, there’s been some dramatic urban renewal happening in recent years for a transformation of hipster proportions. For example, there’s a Google office here.

Exploring Fulton Market in this reinvented West Side district is one of the coolest things to do in Chicago. That’s doubly true if you like food. Go for kebab and mezze at Aba, tuck into good ol’ fashioned barbecue at Green Street Smoked Meats, or classic diner dishes at Little Goat Diner. You’ll love it.

31. Try and spot the sculpture by actual Picasso

Did you know that there’s a secret Picasso statue in Chicago? We bet you didn’t. But there is. And it’s an interesting statue with an interesting story. An Chicago architect wrote Picasso a poem asking him to create a piece. A rare commission for the artist, he accepted because it fit with another “gangster city” he was producing some work for (Marseille).

An untitled piece, it’s one of the coolest things to do in Chicago because it’s sort of interactive – people slide down the bottom of it. Another fun thing to do is guess what it is: Picasso never explained, and today’s eyes see everything from a baboon’s head to an aardvark. Fun fact: it’s in  The Blues Brothers  chase scene.

Chicago is near four different states! If you’re feeling adventurous, you can head out and explore the region in an RV. Otherwise, there are some great places to explore and some other cities that you can go on a tour from Chicago.

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.

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.

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So now that you’ve got all these awesome things to do in Chicago… what now? Well, you’ve got to put some sort of plan into action. Finding out just how you’re supposed to do that, with basically zero knowledge of where things are in the city, can be tricky. Don’t worry though: we’ve come up with this foolproof 3-day Chicago itinerary to suit just about any traveller.

The most iconic parts of Chicago are the ones you should see first. And what’s more, they’re all in the same area, which makes them easy to hit up in one morning. First of all there’s the  Cloud Gate (aka  The Bean ); take a weird selfie in the reflection and then head to the  Crown Fountain , 2 minutes’ walk south. Marvel at the monolithic water spouts and LED faces, then stroll along W Washington St.

Head west and it’ll take you to  Untitled by Picasso . Who knows what it is – a dog, a former lover of the famous artist, a turkey. Make your guess, take a snap or two, then you’ll probably want a snack (or lunch). Get deep dish pizza at  Giordano’s in the Magnificent Mile area, getting the Red Line subway from Lake to Grand/State. Dig in. Enjoy.

Walk off the pizza in a 20 minute stroll to  Navy Pier . This is just about everything: destination, area to explore, sight to see. It’s the perfect place for ambling around, grabbing a donut (you know, for dessert), making it an easy place to spend all afternoon. Top off the evening with a ride in the iconic  Ferris Wheel  here , complete with views over the city. Bonus: it shuts at midnight on the weekend.

Start where you left off the day before (that’s Navy Pier, in case you forget already) and make a beeline for the  Children’s Museum . It opens at 10am, so you’ve got plenty of time to get there and grab a bite to eat for breakfast. It’s fun for pretty much any age and is packed with a load of stuff to see and do.

Now it’s time to head to  Oak Street Beach . Before you get your stroll on though, make sure you grab some lunch – you’ll be hungry by now, trust us. The best place for that, we’d say, Oak Street Beach Restaurant : great food, great views. What more could you ask of your lunchtime spot? People-watch from the restaurant or if the weather’s good lay out on the beach itself and simply chill out.

Walk from here for around 20 minutes for your evening entertainment. Yes, we’re talking the  Blue Man Group . This is some pretty wacky entertainment and one of the more zany option for things to do in Chicago at night. Finish up with some prime spicy Mexican at Flaco’s Tacos , a local chain that’s good for late night eats (and there’s even a happy hour).

Your third day in Chicago starts out with a spot of culture and education at  Chicago History Museum.  Located in  Lincoln Park  it’s open from 9:30am and, once you’re done learning all there is to know about the city’s history, the on-site cafe is a good place to get some food – including vegetarian options. You may want to just opt for a coffee and a snack though, because your next destination is food-mad.

Take the train from nearby Clark/Division on the Red Line and ride 8 stops for 11 minutes to Cermax-Chinatown. Here’s where you’ll find, obviously,  Chinatown . This is the place to soak up Chicago’s Chinese heritage and is a good place for, you guessed it, yet  more  food. Make sure you enter through the ornate Chinese Gate. Explore delicious dishes and make sure to stop at Chiu Quon Bakery for dessert.

Stuffed full of food, it’s time to hop on the Red Line again, from Cermax-Chinatown to Jackson (3 stops, 5 minutes). This is the home of the  Willis Tower . Insane views of the city can be had from here; even better when the city starts to light up at night. Hop on the Blue Line at Monroe and take the train to Damen (11 minutes), where you’ll find The Violet Hour , a speakeasy for post-view drinks.

Don’t forget your travel insurance for Chicago

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

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Here are some quick answers to common questions about what to do and see in Chicago.

Can I do anything in Chicago right now?

Absolutely! Cloud Gate is an iconic sight to see in Chicago, day and night. Airbnb Experiences and GetYourGuide are the best places to find a huge range of activities to do TODAY!

What are good things to do at night in Chicago?

Here are our favourite things to do in Chicago after dark: – See the Blue Man Group – Grab a drink at a Chicago speakeasy – Tour a Re-created Old Jazz Club

What things are good for adults to do in Chicago?

For you grown-ups, we recommend the incredible Adler Planetarium adults-only night. Afterwards, you can visit the unique speakeasies in the city, and top it all off with a classic Chicago Style Pizza.

Are there any free things to do in Chicago?

Oh yes! Oz Park is a must-see for a fun and free excursion. Crown Fountain (especially at night) is a spectacular free show, not to be missed. Oh, and after 3pm Sunday Randolph Street Market has free admission.

The third-most populous city in America, and its second-most visited, Chicago is no secret. Donuts, pizzas, Al Capone tours – throw it all out there and people will nod knowingly. But what Chicago does have is a lot of unusual things to do. It’s a big place with a ton of things to keep your schedule maxed out from day one to the day you wave goodbye to that iconic skyline.

Whether it’s romantic stuff to do in Chicago, or if you need something to keep the kids entertained, we made sure our handy guide has you covered with plenty  to see and do. You’re going to love this place.

Aiden Freeborn

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• The 10 Coolest Neighborhoods In...

The 15 Best Neighborhoods in Chicago

Chicago is a city defined by its distinct neighborhoods, each of which maintains its own personality and culture. These neighborhoods are filled with history, art, music, museums, festivals and so much more. Chicagoans have a lot of pride in the neighborhoods they hail from. Many are worth seeing, but here are 15 of the coolest.

Andersonville.

Located on Chicago’s North Side, Andersonville feels more like an adorable small town than a subset of the city. The streets are lined with beautiful homes and unique local businesses, such as Women and Children First Bookstore, one of the last remaining feminist bookstores in the country; the Andersonville Galleria, which showcases and sells the work of local designers and artists; and AlleyCat Comics, whose entrance is literally in an alley.

Residents of this neighborhood are considered to have pioneered Chicago’s “shop local” movement. It is also one of the most queer-friendly areas of the city. Andersonville is filled with passionate people who stand up for what they believe in and is definitely worth a visit.

Both the University of Chicago and the Museum of Science and Industry lie within Hyde Park’s borders, as does a portion of the beautiful Jackson Park. Hyde Park is also on the shores of Lake Michigan, giving residents and visitors beautiful views and easy access to the 18-mile lakefront running and biking path.

Logan Square

Logan Square is a quiet West Side neighborhood filled with beautiful architecture, lovely parks and a great mix of bars and restaurants. It is also known for its charming Sunday farmer’s market that runs from May through October. While you’re there, be sure to check out Best Intentions, a dive bar owned by two bartending brothers with decades of experience who make unbelievable craft cocktails. Distiller Magazine rated Best Intentions one of the top 22 bars in the world. (Full disclosure: the brothers are the author’s cousins.)

Located on the city’s Lower West Side, Pilsen is a predominantly Mexican-American community with incredible food and art scenes. Visitors to Pilsen will find street vendors selling delicious tacos and elotes, restaurants with live music and cozy local coffee shops. On the art side, gorgeous murals by famous street artists adorn buildings all over the neighborhood. Pilsen is also home to the National Museum of Mexican Art, which offers free admission and whose 10,000-piece collection celebrates Mexican art and culture.

The West Loop is an industrial zone turned chic foodie paradise near Chicago’s business district. It has become a hotspot only over the past decade or so, but Chicagoans flock to this neighborhood for its bevy of modern, upscale bars and restaurants. It is home to the famous Girl and the Goat, where those vying for a table must make reservations months in advance, as well as to the French Market, an indoor food market featuring an eclectic (and delicious) mix of vendors. Other great spots to check out are The Publican, Bar Siena, Duck Duck Goat and Parlor Pizza.

Wrigleyville

The home of the Chicago Cubs’ Wrigley Field, Wrigleyville is a baseball heaven on the North Side of the city. The area surrounding the stadium is lined with souvenir shops and sports bars where fans can enjoy the game. Since the Cubs won the 2016 World Series, the neighborhood has been completely revamped. New hotels, restaurants, bars and shops seem to sprout up every day.

Bronzeville

Bronzeville is considered the center of Chicago’s own 20th-century Harlem Renaissance and is the former South Side home of such greats as Louis Armstrong, Richard Wright, Bessie Coleman and Ida B Wells. It is also the site of Chicago’s Bud Billiken Parade, the largest African American parade in the country, held every August since 1929.

While the neighborhood has experienced significant economic hardship since the Great Depression, it is currently undergoing a revitalization. Not only are new shops and restaurants opening, but the neighborhood is also re-establishing itself as an arts center, with beautiful public art displays as well as the Bronzeville Art District, a group of six visual-arts spaces in the neighborhood. Visitors can even take a free Trolley Tour hosted by the Bronzeville Art District to learn about the neighborhood’s art.

Southport Corridor

The Southport Corridor is a shopping hotspot on the Northeast side of the city, lined with restaurants and clothing stores and also containing the city’s first Amazon bookstore. The Southport Corridor is a fantastic neighborhood in which to spend a Sunday trying on clothes and enjoying a delicious brunch.

This enclave of Lakeview was the first gay neighborhood in the country to gain official recognition by a city government. The neighborhood is marked by a series of rainbow pylons lining its streets, installed in 1998 by Chicago’s then mayor, Richard M Daley, in a historic move to legitimize the neighborhood. Boystown’s main street is filled with queer-focused bars and businesses and is the site of Chicago’s annual June Pride Parade. It is also the location of the Center on Halsted, the largest LGBTQ community center in the Midwest.

Wicker Park

Wicker Park has long been known as one of Chicago’s hipster neighborhoods, anchored by unique local bookshops, cafés, art galleries and cocktail bars. Running through this neighborhood (as well as Logan Square and Humboldt Park) is an elevated 2.7-mile (4.3-kilometer) running and bike path called the 606 – a converted railroad now brimming with beautiful greenery and public art installations.

Old Town is a historic district on Chicago’s North Side, home to beautiful buildings as well as the world-famous comedy club The Second City. If you’re looking for a fancier night out, Old Town offers some great locales. This neighborhood also holds St Michael’s Church, one of only seven buildings to survive the Great Chicago Fire of 1871.

Bridgeport is the location of Guaranteed Rate Stadium, home of the Chicago White Sox. It’s a great neighborhood to visit to catch a game, whether inside the stadium or at one of the area’s many Sox bars. It is considered one of the most diverse neighborhoods in the city, is the birthplace of five Chicago mayors and is also home to the beautiful Bridgeport Art Center, a popular art and event venue.

Rogers Park

Rogers Park is another beautiful lakeside neighborhood and the location of Loyola University. It is the northernmost neighborhood of the city and feels almost like a delightful little town of its own. Rogers Park has a large immigrant population, which also means it has a vast array of delectable restaurant choices, from Peruvian to Indian to Greek to Korean to Pakistani.

Bryn Mawr Historic District

Nestled within the neighborhood of Edgewater lies the beautiful Bryn Mawr Historic District that will have you feeling like you’ve stepped back into the early 1900s. It’s a charming area to wander and enjoy the remarkable architecture.

River North

The swanky neighborhood of River North is near Chicago’s central business district and a popular location for after-work dinner and drinks. It is bursting with bars, restaurants and nightlife and is also home to a number of upscale art galleries. It also lays claim to the famous Wrigley Building, an architectural marvel on Michigan Avenue’s Magnificent Mile. You may know it by its beautiful clock tower reaching into the sky from the building’s center.

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Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

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Home » Travel Guides » United States » Illinois (IL) » 50 Best Things to Do in Chicago (IL) in 2023 by a Local

50 Best Things to Do in Chicago (IL) in 2023 by a Local

The Windy City has awe-inspiring skyscrapers, hunger-stomping food and culture to match almost any city in the world. But what never ceases to amaze me is just how much you can do for free in Chicago. Donations by philanthropists have bestowed the city with superlative museums and more than 700 works of public art, by Picasso, Chagall, Miró – the list is huge. These have turned the skyscraper forest of the Loop and the Millennium Park into one big outdoor gallery.

There are free events too, like Taste of Chicago , the largest food festival in the world, and music festivals to honor the city’s enviable music heritage. Chicago is also great to get around on foot, along the Lakefront Trail or the new Riverwalk, or even underground in the sophisticated Pedway system.

I’m a Chicago local and an avid traveler of my home state Illinois. I’ll guide you through some of the finest attractions the city has to offer, and there’s a lot so I made sure I included something for everyone. Let’s have a look at my list of the best things to do in Chicago :

1. River and Lake Cruises

Out on Lake Michigan and along the Chicago River you can sit back and give Chicago’s cityscape the attention it deserves. There’s a selection of cruises , from gentle lake tours to exhilarating speedboat rides. I took The Classic Lake Tour which is a 40-minute sightseeing trip giving you plenty of time to soak up the sights, and with a recorded commentary for interesting titbits. For the architecture admirers, I’d recommend the guided architecture tour .

At the old Navy Training Center on Navy Pier you can jet off on a speedboat for a 75-Minute Architecture Cruise, starting on the lake and heading upriver as far as the Willis Tower. The Chicago River Architecture Cruise has a more sedate pace, and gives you a clear view of more than 40 listed landmarks, accompanied by live commentary from an expert guide. I’ve done several cruises and think it’s one of the best ways to admire city.

The 442-metre Willis Tower was the tallest building in the world for 25 years, and is is still among the top 25. In my experience the Chicago Skydeck Experience Ticket  is great value for money, you can waste no time, skipping the line and speeding up to the Skydeck 412.4 metres above the west side of the Loop.

On the meandering route to the elevator, there’s a movie detailing the 45-year history of the Willis Tower and Chicago’s other architectural wonders. After a swift ride you’ll be struck by a view extending over 50 miles and four states. The Ledge at the Skydeck will either give you a buzz or make your stomach flutter: This is a set of four all-glass boxes projecting over a sheer drop of more than 100 storeys. While this was an amazing experience I realized I didn’t like heights as much as I thought.

3. Food Tours

If it’s big portions and bold flavors you’re after, Chicago is the town for you. Chicago may be America’s top food city, and you would be brave to disagree. The staples are deep-dish pizza, hot dogs piled with seven toppings, Italian beef sandwiches, brownies and beer. Lou Mitchell’s and Twin Anchors have nationwide fame, but if you want local spots that might escape the attention of out-of-towners, there are a range of tours for hungry visitors.

The Secret Food Tour lets you in on these undisclosed locations. You can also take a Tasting Tour of Chinatown on foot. A nice alternative is filling up up on Mexican tortas and Polish pierogis on a Bike Tour .

4. Art Institute of Chicago

Three of the most studied and celebrated paintings of the past 150 years await at an art museum to match the best in the world. These works are Nighthawks by Edward Hopper, American Gothic by Grant Wood and Seurat’s A Sunday Afternoon on the Island of La Grande Jatte. They are all obligatory, as is Picasso’s Old Guitarist, but are only a gateway to a whole feast of art.

The Art Institute of Chicago has the largest collection of Impressionist and Post-Impressionist painting outside Paris, with more than 30 paintings by Monet, as well as works by Cézanne, Renoir, van Gogh and Toulouse-Lautrec.

For modern art there’s Jackson Pollock, Warhol, Jasper Johns and Matisse, while the modern architecture and design collection has drawings and models by Frank Lloyd Wright, Le Corbusier and more.

You can also delight in ancient Greek, Egyptian, Etruscan and Roman artifacts, from mosaics, to pottery, glass, coins, bronze and jewelry. If you don’t want to stand in line for tickets I suggest booking a ticket online. I recommended planning to spend at least a few hours at the museum as there’s a lot to see.

Related article : You may also like my guide on the most beautiful places to visit in Illinois .

5. Grant Park

Affectionately known as “Chicago’s front yard”, Grant Park fronts the Loop on Lake Michigan and is the city’s prime open space. These 319 acres contain lots of Chicago’s top attractions like Millennium Park, the Museum Campus Chicago, the Art Institute of Chicago, Maggie Daley Park and the epic Soldier Field, home of the Chicago Bears NFL team.

You could write a whole article on Grant Park and the layers of things to do in its boundaries. But it’s also worth remembering that the park is a lively place for Chicagoans just to unwind and be active, with baseball diamonds, tennis courts and lush boulevards to wander down.

In July Grant Park hosts the Taste of Chicago Festival, the biggest food event anywhere, and in October is the start and finish line for the Chicago Marathon.

6. Millennium Park

Created to herald the new millennium, this award-winning space in Grant Park is the most popular visitor attraction in the Midwest. Free to enter, the Millennium Park has bold public art, spellbinding architecture and some forward-thinking initiatives.

For a taste, the 2.5-acre Lurie Garden is part of the world’s largest green roof, while the McDonald’s Cycle Center is a sleek indoor bike station offering rental, repair and an array of services for Chicago’s cyclists. I’ll bring up a few of the showpiece sights in Millennium Park later, but you can’t miss the Jay Pritzker Pavilion.

This 11,000-capacity band-shell was conceived by Frank Gehry, and from spring to autumn has a packed calendar of concerts by major recording artists and the likes of the Chicago Symphony Orchestra and the Lyric Opera of Chicago.

7. Riverwalk

Chicago is a city that knows how to treat pedestrians, as you’ll see along the main branch of the Chicago River as it cuts through the downtown . A feat of urban planning, the Riverwalk is 1.25 miles long, made up of six coves or “rooms” up to Wolf Point. The route will take you past photo opportunities like the Wrigley Building and a whole of host of head-turning works of public art.

These might be bright graffiti panels or large-scale installations like Ellen Lanyon’s Gateway, recording Chicago’s story through 28 ceramic tile murals. You can board a cruise boat or water taxi of course, or take matters into your own hands on an urban kayak or “cycleboat” tour. With dramatic urban scenery, terraces stepping down to the water and bars grills and cafes, it’s no shock that the Riverwalk has become a go-to on date night.

8. Navy Pier

Set where the Chicago Portage enters Lake Michigan, the Navy Pier is a multifaceted visitor attraction extending over the water for six city blocks. As one of the top days out in the Midwest, an attraction of this magnitude is hard to sum up in one paragraph. But in 50 acres you’ll come across the vast multisensory Funhouse Maze and, my personal favorite, the nearly 200 feet Centennial Wheel, footed by fairground rides and amusements.

There’s also weekly fireworks in summer, an IMAX Theatre, the Chicago Children’s Museum and the Crystal Gardens botanical garden with more than 80 palms. You can use the pier as the jumping off point for cruises on the lake or river, take in some live music at the Miller Lite Beer Garden and watch the drama unfold at the non-profit Chicago Shakespeare Theater.

9. Cloud Gate

The anchor for the AT&T Plaza in Millennium Park is an enchanting piece of public sculpture by Anish Kapoor. Installed in 2006 and affectionately dubbed “The Bean”, Cloud Gate is a rounded arch, clad with 168 highly reflective stainless steel plates. After a few teething problems due to its complicated design, Cloud Gate has quickly become an emblem for 21st-century Chicago.

The monument was designed to bring to mind a blob of liquid mercury, and its value lies in how interactive it is. You can take photos of your own reflection against the distorted Chicago skyline, and while passing under the 12 foot, look up into the “omphalos”, a concave chamber that twists and multiplies reflections. I’ve seen countless tourists take a selfie here, it’s quickly become one of the most iconic sculptures in Chicago. Fun fact: it’s nicknamed ‘The Bean’ because of its shape.

10. John Hancock Center

A mainstay of Chicago’s silhouette, 875 North Michigan Avenue (formerly the John Hancock Center) is a 1,500 feet skyscraper on the Magnificent Mile. Tapering as it rises, the tower was topped off in 1969 and appears in pretty much any movie that needs an establishing shot for Chicago. Up close you can watch its characteristic X-shaped bracing zigzag up the facades.

The view from 360 Chicago on the 94th floor has been rated as one of the best in the country, and the ride up there takes less than 40 seconds. There’s a cafe and bar up, as well as interactive displays labeling the landmarks on the horizon in each direction. If you have a steely disposition try “Tilt”, a glass capsule that tilts forward at 15°, 25° and 40° for a bird’s eye view of the city streets 1,500 feet below. Might seem obvious but I recommend visiting on a clear day so you have a great view of the city.

Also see :  Amazing Hidden Gems in Illinois

11. Chicago Cultural Center

Formerly the home of the Chicago Public Library, in 1991 this striking Neoclassical building in The Loop became the first free municipal cultural center in the United States. There are more than 1,000 exhibitions and  here every year and they’re as diverse as you’d expect from a city like Chicago.

All for free, you can catch theater, dance, music, lectures, film screenings and family-oriented events.

No matter what’s on, you have to take the opportunity to look inside this building from 1897. The nation’s top craftsmen were hired for the interiors, working with valuable materials like fine hardwood, rare imported marble, polished brass and mother-of-pearl.

The two domes are not to be missed: The south is the largest stained glass Tiffany dome in the world, while the larger Renaissance-style dome on the north side is 12 meters in diameter and has 50,000 glass panels. I recommend visiting their website for more info on exhibits and tours.

12. Wrigley Field

The Chicago Cubs play at the second-oldest ballpark in the Major League. Wrigley Field (1914), nicknamed “The Friendly Confines” by the legendary Ernie Banks, is noted for its ivy-clad outfield walls and has an iconic manual scoreboard.

The stadium may catch you off-guard, as it sits in the middle of a residential neighborhood and has no car park, now a rarity for US sports venues. The wind blowing towards or away from Lake Michigan (out or in) can turn potential home runs into outs, or send balls out of the stadium altogether.

Come to see the 2016 World Champions at one of 66 regular season games, checking out the famous red entrance marquee from 1934 and to treat yourself to a Chicago hot dog .

As parking can be a nightmare I suggest to either to take a cab or to take the Red Line to get there.

13. Maggie Daley Park

In Chicago with kids? Visit Maggie Daley Park! Named for a former first lady of the city who passed away in 2011, Maggie Daley Park is one of Grant Park’s newest treasures.

Laid out by landscape architect Michael Van Valkenburgh, the park opened in the northeast corner of Grant Park 2014 and shines for its recreation and family facilities.

The whimsical Play Garden, for kids up to 12, is a playground like you’ve never seen, with six different zones like the Watering Hole which has a giant breaching whale, and the Enchanted Forest where you’ll walk under upside down trees . There’s also an ice skating ribbon, a quarter of a mile in length, picnic groves, an 18-hole mini golf course and rock-climbing walls.

14. Richard H. Driehaus Museum

In the Driehaus Museum you’ll step back into America’s Gilded Age at the refined Nickerson House, built in 1883 for the banker Samuel M. Nickerson. Close to the Magnificent Mile, on the Near North Side, the house looks a little out of place, dwarfed by the city’s bold Neoclassical monuments and glass-clad skyscrapers.

In 2003 the Chicago fund manager and philanthropist turned the Nickerson house into a museum, blending the original furnishings with luxurious Art Nouveau glazed tiles, stained glass, onyx, carvings and marble all sourced from other places.

The museum is heaven if you like decorative arts. You’ll find some lovely pieces by Louis Comfort Tiffany, like a large fire screen, a set of vibrant stemware, a blown-glass humidor and a peculiar centerpiece lamp.

The ballroom has Edward Colonna furniture you can sit in, while some other exceptional pieces include Sèvres vases, a suite of George A. Schastey neo-Empire chairs, pre-Raphaelite paintings and a rare Chickering and Sons grand piano. In case you’re looking for a bite I had a great pizza at nearby Giordano’s.

15. Buckingham Fountain

At the center of Grant Park, between the ornamental North and South Rose Gardens is a sight that needs a double take. Hewn from Georgia pink marble, the Buckingham Fountain (1927) is one of the largest in the world, nearly 280 feet in diameter, with nearly 200 jets and a pool.

The Rococo design is borrowed from the Latona Fountain at Versailles, and is an allegory for Lake Michigan, with four pairs of sea horses representing the states of Illinois, Wisconsin, Michigan and Indiana.

At any one time there’s 1.5 million gallons of water in the Buckingham Fountain. Stop by for the 20-minute water display on the hour, shooting jets up to high into the air.

16. Lakefront Trail

Eighteen miles of Chicago’s shoreline can be accessed on a waterfront path, threading through all four of the city’s lakeside parks. The Lakefront Trail is shared by cyclists, joggers and families.

People use the trail to get to work, and to stroll next to Lake Michigan and savor Chicago’s skyline. You can use the path to get to a whole catalog of interesting places, from the South Shore Cultural Center to Navy Pier and the Shedd Aquarium.

In summer you can hop from beach to beach and to get a dose of greenery at Grant Park or Lincoln Park. There are bike rental companies all along the trail, or you could buy a day pass for Divvy, Chicago’s bike sharing system. This is actually one of my favorite places to go jogging with my dog.

17. Museum of Science and Industry

Limitless inspiration for kids, the Museum of Science and Industry has show-stopping exhibits on an amazing scale. The venue is the old Palace of Fine Arts, built in 1933 in Jackson Park for the World’s Columbian Exposition.

Some of the jaw-dropping sights here are a full-size German U-505 submarine captured during the Second World War, the Pioneer Zephyr, a glorious stainless steel diesel locomotive from 1934 and the first Boeing 727 to enter commercial service.

Young scientists can wrap their heads around big concepts at the Science Storms exhibit, which has a Tesla coil, Foucault pendulum and Wimshurst machine.

There are relics from the Apollo missions at the Henry Crown Space Center , while the central pavilion has a replica of a deep-shaft bituminous coal mine, in which you’ll take a mine train and see historic equipment from the 1930s.

18. Magnificent Mile

Squeezed into eight blocks on the arterial Michigan Avenue is a whole world of shopping, entertainment, dining, dazzling architecture and more things to do than you could manage in a whole holiday. Many of the sights or attractions on my list are on this street, or a stone’s throw from it.

There are 275 restaurants and more than 460 retailers here, from flagship stores for Zara, Disney and Nike to scores of boutiques and ritzy emporia for Rolex, Boss, Burberry and any other high end brand you can think of.

Soaring overhead are icons of the Chicago skyline like the Tribune Tower (1925) and the Wrigley Building (1924) in the south and 875 N Michigan (1969) towards the north end.

For a more unassuming sight, stop for a snap of the castle-like Chicago Water Tower, dating to 1869 and the second oldest surviving water tower in the United States.

19. Garfield Park Conservatory

Well west of the Chicago Loop, Garfield Park warrants the 15-minute cab ride into a slightly down-at-heel neighborhood. The trip is for the world’s third largest garden under glass, an astounding botanical conservatory with eight indoor display gardens. The conservatory was completed in 1908 and designed to resemble the haystacks of the Midwest. As it’s indoors I’d recommend this activity if there’s a rainy day forecast during your trip.

The moment you step inside you’ll be in the Palm House with more than 80 varieties of palm tree. Also see the incredible ferns and cycads against the waterfall in the Fen Room, and one of the nation’s most varied collections of cactuses and succulents in the Desert House.

Come by any day in summer and there will be something going on, like free yoga, gardening demonstrations and a chance for kids to get up close to animals like harmless snakes and goats.

20. Mob and Crime Bus Tour

Now their misdeeds are in the distant past, there’s no denying the fascination evoked by Chicago’s prohibition-era mobsters. Names like Al Capone, Bugs Moran and Dion Johnny Torrio remain household names.

The city has changed so much in the last century that you’d never guess that benign looking neighborhoods witnessed a bitter war that claimed scores of lives in the 1920s and 30s. So you have to turn to local historians, and I found that GetYourGuide.com offers a 90-minute Mob and Crime Bus Tour . A similar tour is available on Viator as well.

This uncovers the dark past of the Windy City, profiling notorious men like Capone and John Dillinger. You’ll visit the site of the Valentine’s Day Massacre and the Biograph Theatre, where Dillinger was gunned down by FBI agents.

21. Shedd Aquarium

Sharing the Museum Campus Chicago with the Field Museum and the Adler Planetarium, the Shedd Aquarium (1930) was for some time the largest indoor aquarium in the world. Donated by the philanthropist John G. Shedd, the attraction has an incredible 32,500 aquatic creatures from across the planet.

These are in immersive zones like Amazon Rising, which has caimans, anacondas, piranhas and freshwater stingrays in tanks among the roots of rain-forest trees. Also mandatory are the Caribbean Reef, housing a rescued green sea turtle, the Wild Reef with four varieties of sharks and the historic Waters of the World gallery home to colorful starfish and seahorses.

Stingray Touch lets you find out what a cownose ray or yellow spotted ray feels like, while marine mammals like sea lions, penguins and sea otters can be found in the Oceanarium.

22. Field Museum of Natural History

One of the best and largest natural history museums in the world, the Field Museum’s museum collection has swelled to more than 24 million objects since it opened in 1893. This a place to feed your fascination for the natural world, with grand Neoclassical halls housing fossils, priceless gemstones and animal and plant specimens.

There’s also compelling anthropology for the Ancient Americas and Ancient Egypt, as well as Tibet, China, Africa and cultures in the Pacific Islands. The Geology Halls meanwhile have an exquisite collection of Chinese jade, and a stained glass window by Louis Comfort Tiffany.

The star of the show is the 28 feet tall Titanosaur in the Stanley Field Hall. In 2018, this herbivore from Argentina replaced SUE, a T-Rex specimen, which will reappear at the Evolving Planet Gallery in 2019. It took me a few hours to explore the entire museum so great value for money.

23. United Center

There was a time in the 90s when a seat at the United Center was the hottest ticket in town.

The Chicago Bulls moved to this arena in 1994 when Michael Jordan was on his strange hiatus in Minor League Baseball, and he’d return to lead them to three straight titles between 1996 and 1998. Out on the east side of the building is a statue in his honor, named The Spirit and showing him mid-dunk.

Fair to say that the 2010s aren’t a golden age for the Chicago Bulls, but if you are a fan or want to make a pilgrimage to this hallowed ground you can watch a game in the regular season from October to April.

At roughly the same time of year, the Bulls share the United Center with the Chicago Blackhawks NHL team, which has had a much more successful decade, winning the Stanley Cup in 2010, 2013 and 2015.

24. Chicago History Museum

In Lincoln Park you can lift the lid on Chicago’s rich history, perusing fascinating thematic exhibitions. Facing Freedom goes into depth on the various struggles for freedom to beset Chicago from the 1850s to the 1970s, covering the Civil War, Women’s Suffrage, the formation of labor unions and Japanese internment.

At Crossroads of America you can step into a jazz club or climb aboard Chicago’s very first L train, while the Chicago dioramas tracks Chicago’s breakneck rise from a lonely frontier outpost to an immense metropolis.

Sensing Chicago lets kids jump into a gigantic Chicago-style hot dog, ride a vintage high wheel bike and hear the roar of the Great Chicago Fire.

25. Lincoln Park Zoo

In 37 acres and dating back to 1868, this zoo deserves extra credit as one of the last remaining free admission animal parks in the United States. There are more than 1,100 animals here, in habitats that are constantly being revamped.

The polar bear and African penguin enclosures for instance have just been reopened, while a recent arrival in 2014 is the Regenstein Macaque Forest where you can see Japanese macaques bathing in a hot spring as they do in the wild.

There’s a hint of the great age of the zoo at the Kovler Lion House, constructed in 1912, while some other family favorites to tick off are the Helen Brach Primate House (1927), seal pool, family petting zoo, the superb Regenstein Center for African Apes and the Regenstein African Journey. This has indoor and outdoor habitats for giraffes, pygmy hippos, ostriches, gazelles and many more.

Best of all might be that entrance is free. However parking costs can be quite expensive so I’d recommend going there by public transportation, or foot if you’re located close by.

26. Chicago Picasso

Pablo Picasso produced this monumental piece of public art for Chicago in the mid-1960s. Standing in Daley Plaza, the Chicago Picasso weighs almost 147 metric tons and stands over 50 feet tall.

Since it was unveiled in 1967, the work, rumored to depict French model Lydia Corbett who sat for a series of drawings for Picasso in the 1950s, is a landmark for the city and something for kids to clamber on.

Early on, in a city that previously only dedicated statues to historical figures, the Chicago Picasso was a source of controversy, but now inspires affection as a famous meeting point and backdrop to public events on Daley Plaza like the Christkindlmarkt at Christmas.

27. Holy Name Cathedral

Chicago’s Gothic Revival Catholic cathedral, by Chicago Station on the Red Line, was completed in 1875 after its predecessor burnt down in the Great Chicago Fire of 1871. Eagle-eyed visitors will be able to spot an overarching Tree of Life Theme in the building’s fittings.

On arrival you’ll be confronted by the cathedral’s immense bronze doors, each weighing more than 500 kilos and cast to resemble planks of wood.

Inside, a few of the fixtures worth closer inspection are the Stations of the Cross in red Rocco Alicante marble, bronze sculptures depicting the Evangelists and the cathedra (bishop’s throne) for the Chicago Diocese.

There’s also a slice of Chicago gangland history outside, where a cornerstone inscription is still chipped from the 1926 murder of mob boss and Al Capone rival Hymie Weiss.

28. North Avenue Beach

Another of the many things to love about Chicago is the way the city has been planned to grant access to the lakeshore. In hot weather this means you can slip off your shoes and set foot in Lake Michigan, or plan a whole day at the beach. Being slightly removed from the fabric of the city, Lincoln Park has what many people agree to be the best beach in the city.

North Avenue Beach runs for a few hundred yards up to Diversey Harbor, with piers at short intervals to stop the sand being washed away. There’s a bar on the beachfront, as well as companies offering rentals and tuition for kayaking and stand-up paddleboarding.

International competitions take place at the South Volleyball Courts here, while in August North Avenue Beach is the place to catch the Chicago Air & Water Show.

29. Crown Fountain

The wonders keep coming in the Millennium Park, because we haven’t even mentioned the Crown Fountain (2004) yet. Here the Catalan artist Jaume Plensa designed two glass brick towers, 15 meters in height. They face each other across a black granite reflecting pool.

Those glass bricks are installed with LEDs displaying changing photographic facial images of citizens’ faces, filling the towers. For a playful touch, water spouts from the a nozzle between their lips from May to October.

Like most of the works in the Millennium Park the Crown Fountain is interactive, and on hot summer days you’ll see children paddling in the reflecting pools and cooling off under the waterfalls that cascade down the sides of the towers.

30. Michigan Avenue Bridge

The Burnham Plan of 1909 helped shape Chicago’s cityscape, and brought about this trunnion bascule bridge conducting Michigan Avenue over the main branch of the Chicago River. An official Chicago Landmark, the bridge opened in 1920 and once completed helped spur the flurry of development that gave rise to the Magnificent Mile.

Be sure to go in for a closer look at the north and south pylons, which have bold reliefs depicting scenes from Chicago’s past, carved by Henry Hering and James Earle Frasier respectively. The south pylons depict Defence and Regeneration, while the north pylons show the Discovers and Pioneers.

The southwest bridgehouse holds the McCormick Bridgehouse & Chicago River Museum, chronicling the history of the bridge and the Chicago River. If you’re in for a burger I recommend the nearby Billy Goat Tavern which has a delicious cheeseburger.

31. Robie House

To look at this house on the University of Chicago campus and know nothing about its origins, you’d never guess that it was built in 1910. Residential architecture would never be the same after the great Frank Lloyd Wright designed this home for Frederick C. Robie, the assistant manager of a company on the South Side.

The Robie House is considered the pinnacle of the early-20th-century Prairie style, and you can go in for tours Thursday to Monday.

The Prairie style expresses the sense of space in the prairie landscape of the Midwest, and this is captured by the low profile, long cantilevered eaves, broad balconies and even the use of narrow red bricks.

The Robie House has marvelous art-glass throughout, personally designed by Wright, along with the house’s curtains, rugs, furniture, bathroom fittings, fireplaces and lighting.

32. Museum of Contemporary Art

Dedicated to art from 1945 to the present, the Museum of Contemporary art is endowed with a serious collection, spanning surrealism, conceptual art, pop art and minimalism. You’ll get to see works by Chuck Close, Andy Warhol, Jasper Johns, Francis Bacon, René Magritte, Alexander Calder, Ann Hamilton and Richard Serra.

From June to September, Tuesdays on the Terrace is a programme of summer performances by members of Chicago’s dynamic jazz community.

33. Symphony Center

As one of America’s “Big Five”, the Chicago Symphony Orchestra is among the most prestigious classical ensembles on the planet. You can see them at the Symphony Center, a National Historic Landmark on South Michigan Avenue.

This venue is a complex made up of the Grainger Ballroom, Buntrock Hall and the 2,522-seater Orchestra Hall. On the frieze above the facade’s arches windows you’ll read the names “Bach, Mozart, Beethoven, Schubert and Wagner”. By 2018 Riccardo Muti had been the conductor for eight years.

34. Second City Chicago

An absurd amount of comic talent has come out of Chicago over the last 60 years, and one of the reasons for that is Second City. This fabled comedy club and improv company on Wells Street counts Steve Carell, Billy Murray, Tina Fey, Amy Poehler, Stephen Colbert, Dan Aykroyd, John Belushi and John Candy among its alumni.

There are three stages at Second City, “Mainstage” and “e.t.c. Stage” for sketch comedy and improv acts, and the UP Comedy Club for stand-up. Chances are you’ll get see a future TV or film star honing their comedic powers here.

35. Chicago Theater

One of five Tony award-winning venues in Chicago, the Chicago Theater warrants a photo, even if you’re not planning to see a show. That’s partly because of the marquee and vertical sign, which often appear in movies set in the city.

The venue opened in 1921 as an opulent motion picture house, and if you step back across State Street you can get a good look at the facade. This has a beautiful central arch that mirrors the false-perspective effect of the Palazzo Barberini in Rome, and is glazed with Tiffany stained glass.

Now one of Chicago’s best spots for performing arts, the theater is owned by the Madison Square Garden Company and puts on a varied program of comedians, world-famous musicians, dance companies and lectures by renowned cultural figures. Madonna, Hamilton, Trevor Noah and more are all in store for this year. I recommend checking their event calendar.

36. Oriental Institute Museum

While you’re down at the Robie House, head to this awesome museum at the University of Chicago’s Oriental Institute. Opened with funding from John D. Rockefeller Jr., the ivy-clad museum is a treasure chest of ancient artifacts discovered during digs in Turkey, Israel, Egypt, Iran, Iraq and Syria.

A couple of the most remarkable exhibits are an imposing statue of King Tutankhamen and a giant human-headed winged bull from the Assyrian city of Khorsabad.

From around the same period there’s a set of ornate Luristan Bronzes produced in western Iran in the early Iron Age, and a stunning array of paper-thin ivories carved in the ancient city of Tel Megiddo, now northern Israel.

Like so many places on this list, I really like that the museum is free (it does encourage donations).

37. Tribune Tower

Built in the mid-1920s for the Chicago Tribune, this iconic Gothic Revival skyscraper on the Magnificent Mile is now being turned into condominiums. The Tribune Tower is clad with Indiana limestone, and came about after a design competition to mark the paper’s 75th anniversary.

At night you’ll get a clear view of the buttresses and tracery at the very top, while there are lots of details to discover on the lower storys. In the years before the tower went up, the Tribune’s publisher Robert R. McCormick had asked his correspondents to bring him fragments of famous monuments from around the world.

So, embedded in the stonework are pieces from the Hagia Sophia, Taj Mahal, the Butter Tower of Rouen Cathedral, the Alamo, the Great Pyramid and the Great Wall of China, to name a few.

38. Adler Planetarium

In Grant Park, the Adler Planetarium (1930) is both a respected institution at the Museum Campus and a noble landmark in its own right. The planetarium occupies a nub of land sticking out over the lake on Northerly Island. By the water to the north is the Adler Planetarium Skyline Walk, blessed with the ultimate view of Chicago’s skyline.

Inside, kids can interact with exhibits dealing with topics like the Solar System, the composition of planets and the Moon missions. You can also find more fact-heavy exhibitions about the history of telescopy and the origins of the universe.

Projected shows are the cornerstone of any planetarium, and the Adler has a big choice, showing the sky above Chicago with light pollution filtered out, and sparkling presentations about the mysterious Planet Nine and nebulae.

39. Chicago Children’s Museum

The Chicago Children’s Museum, which I first visited in my younger years on a school trip, promises a few hours of active, engaging fun for youngsters. On Navy Pier the museum has 15 interactive exhibits over three storys, each mixing play with learning.

In that spirit, the Tinkering Lab for instance features genuine tools and materials giving kids the freedom to create whatever comes to mind, while Skyline is a crash course in architectural engineering, letting children experiment with skyscraper designs.

Play It Safe is a fun indoor play zone in partnership with the city’s Fire Department, teaching little ones about fire safety as they escape from a room filled with pretend smoke and shoot down a fire station pole.

There’s a whole calendar of special activities and workshops, and something different happening on a every visit.

40. Chicago Shakespeare Theater (CST)

Based on Navy Pier, this adored non-profit theater company has done as much as anyone to help keep Chicago on the cultural map over the last 30 years.

In short order the theater has earned three Laurence Olivier Awards, as well as a regional Tony in 2008. Its main aim is to introduce people to the works of William Shakespeare, through school tours, summer plays in parks and productions at its own majestic venue, adding up to 600 performances a year.

The Chicago Shakespeare Theater has been at Navy Pier since 1999, in a complex with two auditoriums: The 510-seater Courtyard Theater and the more intimate Upstairs theater.

The program is crafted for everyone, and has meaty productions of Macbeth and Hamlet, and light family musicals like Peter Pan and Bedknobs and Broomsticks.

41. Alfred Caldwell Lily Pool

People go out of their way to visit a masterpiece of landscape architecture in Lincoln Park. This pond is named after its designer, Alfred Caldwell who worked on it in the second half of the 1930s.

In the same vein as the Robie House, the environment is laid out in the Prairie style. You’ll definitely sense the Prairie school’s love for low horizontal forms and the natural landscapes of the Midwest.

A National Historic Landmark since 2006, the pool is traced by winding stepping-stone paths, wide stratified slabs of limestone, circular benches, plants native to the Midwest, a waterfall and waterside pavilion.

42. Peggy Notebaert Nature Museum

This child-friendly museum in Lincoln Park presents the natural history of the Chicago region in smart and interactive ways.

As an institution the museum was founded back in 1857 and moved into a new home in the park in 1999. The old museum, now used by the zoo, was known for its detailed static dioramas, and while these are still here, they’re joined by spellbinding living environments like the astonishing Judy Istock Butterfly house, where 1,000 butterflies flutter in a 250-square-meter greenhouse.

During the “Critter Connection” every day at 11:30 kids can get an up close look at more than a dozen different amphibian species at the Animal House.

There’s also a bird walk, leading to a platform over Lincoln Park’s North Pond, as well as hands-on stations where kids can learn about rivers, solve nature-inspired puzzles and explore a beaver lodge.

43. Chicago Pedway

Under the city streets and spanning more than 40 blocks north to south, Chicago has a vast network of pedestrian tunnels, as an answer the vicious winter weather and to provide easy links between “L” stations.

The oldest sections, between State and Dearborn streets date back to before the Second World War. The rest of the network was begun in the 1950s and expanded in the 60s and 70s. Not all of the Pedway is subterranean, as there are enclosed raised footbridges.

As ever, there are works of public art adorning the tunnels, along with restaurants and shops. In the Pedway by Macy’s check out the beautiful display of 22 stained glass panels, a holdover from the defunct Smith Museum of Stained Glass. There are free walking tours available but in my experience the free tours cost you just as much, because at the end of the tour they do ask to contribute whatever price you think the tour is worth and most people will feel obligated to pay a decent price.

44. Chinatown

Strolling along the Chicago River you’re sure to see the yellow Chicago Water Taxi zipping past. In this part of the city, these boats stop at Michigan Avenue and further west along the Riverwalk. One idea for a trip is to catch the taxi down to Chinatown.

The scenic journey through the Loop and South Loop will take about 40 minutes and there are services all day in summer, but especially around lunchtime. And that’s because one Chinatown is a Dim Sum paradise.

Head for Dolo Restaurant and Bar and MingHin Cuisine where there are so many options you won’t know where to start. But people come a long way for MingHin’s Macau pork belly at deep fried taro puffs. I started exploring from Chinatown Square which is a great place to start.

45. Chagall’s Four Seasons

Under a glass canopy at the Chase Tower Plaza in the Loop is another exceptional piece of public art ready to enchant passers-by. This figurative mosaic is by Marc Chagall and was donated by the stockbroker Frederick H. Prince. The Four Seasons is big by any measure. I’ve walked by countless times and each time I take a sec to admire it.

It is made up tens of thousands of inland chips in more than 250 colors, and has hints of the Chicago skyline, suns, flowers, birds, fish , lovers and musicians. While we’re talking about Chagall – when the artist came to install the mosaic in the 70s he produced a set of stained glass windows for the Art Institute of Chicago to celebrate America’s Bicentennial.

They are among the most treasured works in the collection, and you may recognize them if you’ve seen Ferris Bueller’s Day Off!

46. Brookfield Zoo

A Metra train ride out to the suburb of Brookfield, this zoo is in 216 acres of green parkland and boasts more than 450 species. The Brookfield Zoo made waves when it opened in 1934 as it pioneered the use of moats and ditches instead of cages, and was also the first in America to have giant pandas. I loved wandering around and enjoyed spotting all the different animals.

One of the most recent additions is the Great Bear Wilderness, letting you get within inches of North Americas mightiest carnivores. Also new is Wild Encounters, where you can pet tame goats, walk through a wallaby enclosure and enter one of the largest free-flight parakeet aviaries in the world.

Naturally, kids’ favorites (and mine too) like big cats, rhinos, giraffes are all at Brookfield Zoo, while Humboldt penguins are the stars at the Living Coast habitat.

47. Live Music

In a city that gave its name to whole genres of blues and house music, you can bet that Chicago is a big live music town. To tap into the city’s jazz and blues heritage, look for a few spots that have achieved legendary status.

This an apt time to bring up Buddy Guy’s Legends, founded by the blues veteran on South Wabash in 1989, and where he still plays a series of shows every January.

Kingston Mines in Lincoln Park dates back to 1969 and has two live shows a night without fail, while the venerable Green Mill Cocktail Lounge (1907) was run by mobsters in the Prohibition era, and Al Capone’s favourite booth is still here.

On a wider scale, there are 225 live music venues in all, as well as some of the nation’s most exciting festivals, both free and ticketed, from the Chicago Jazz Festival to Lollapalooza and Pitchfork.

48. Taste of Chicago Festival

In mid-July Grant Park puts on the world’s largest food festival. The Taste of Chicago Festival drives home the full diversity of Chicago’s dining options.

Bring an appetite and you can take a culinary trip around the world, discover the creativity of Chicago’s contemporary restaurants or renew your love affair with Chicago classics like Italian beef, cheesecake, pizza and hot dogs.

There are pop-up restaurants, a whole armada of streetfood trucks and stands representing Chicago’s top eateries. You can go sample crazy, or see highly skilled chefs doing their thing at live demonstrations. And as the perfect accompaniment the festival organizes live music by famous acts and the best of Chicago’s music scene.

49. Chicago Jazz Festival

This totally free four-day music extravaganza takes place across the Labor Day weekend in Millennium Park. The event is now in its fifth decade, and dates back to 1974, when a festival was organised in Grant Park to honor Duke Ellington who had just passed away.

The list of performers who have taken the stage at the Chicago Jazz Festival is a who’s who of jazz, gilded with names like Dizzy Gillespie, Ella Fitzgerald, Miles Davis and Sun Ra. Each year there’s a helping of Jazz royalty sharing the bill with stars of contemporary jazz and some undiscovered talent.

Shows take place at the pavilions in Millennium Park (headliners play at the Jay Pritzker Pavilion), as well as Chicago Cultural Center.

50. Chicago Air & Water Show

To round the whole thing off, here’s another big event that the city lays on for free. The Chicago Air & Water Show goes back to 1959 and remains the city’s second favorite festival, as well as the largest free show of its kind in the United States.

Across a weekend in mid-August more than two million people line Lake Michigan, particularly the North Avenue Beach, for an exhibition of supersonic jets, formation flying, sky-diving and skywriting.

These are normally Army and Air Force groups, like the Golden Knights parachute team and the U.S. Air Force Thunderbirds.

Tip: There’s no better time to visit 360 Chicago, the Skydeck or take a cruise on the lake, while shore-side restaurants and bars put on viewing parties, though tickets will sell out months in advance.

I truly hope you enjoyed my picks for Chicago, if you have any comments or tips feel free to contact us !

50 Best Things to Do in Chicago (IL) in 2023 by a Local:

• River and Lake Cruises
• Art Institute of Chicago
• Millennium Park
• John Hancock Center
• Chicago Cultural Center
• Wrigley Field
• Maggie Daley Park
• Richard H. Driehaus Museum
• Buckingham Fountain
• Lakefront Trail
• Museum of Science and Industry
• Magnificent Mile
• Garfield Park Conservatory
• Mob and Crime Bus Tour
• Shedd Aquarium
• Field Museum of Natural History
• United Center
• Chicago History Museum
• Lincoln Park Zoo
• Chicago Picasso
• Holy Name Cathedral
• North Avenue Beach
• Crown Fountain
• Michigan Avenue Bridge
• Robie House
• Museum of Contemporary Art
• Symphony Center
• Second City Chicago
• Chicago Theater
• Oriental Institute Museum
• Tribune Tower
• Adler Planetarium
• Chicago Children's Museum
• Chicago Shakespeare Theater (CST)
• Alfred Caldwell Lily Pool
• Peggy Notebaert Nature Museum
• Chicago Pedway
• Chagall's Four Seasons
• Brookfield Zoo
• Taste of Chicago Festival
• Chicago Jazz Festival
• Chicago Air & Water Show

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57 Coolest Things to Do in Chicago for 2023

There are so many cool things to do in Chicago, I’ve been twice and I’d totally go back for the hat trick. I love it there. 

If you’re looking for what to do in Chicago, then read on my friend. I’ve listed all the coolest activities in Chicago worth doing so you can have the best trip ever. You’re welcome. 

This big, beautiful, lakeside city in the state of Illinois deserves a whole lot of cheesy love because it’s one of the quirkiest around. Home to dozens of museums, deep dish pizza and the Obamas, Jennifer Hudson and Bill Murray, it’s just that bit cooler than New York IMHO. 

I love the fact there’s a beach, the views from the high points are amazing, and once you’re done with the bright lights of the city centre, you can go and explore the unique personalities of the 77 Chicago neighbourhoods.

Coolest Things to Do in Chicago

1. Let’s start with the most famous Chicago activity of them all, getting a photo by the Cloud Gate – better known as The Bean. 

2. Enjoy a park with a difference by walking along the 606 . It’s an abandoned railway come recreational space 2.7-miles long complete with art installations, plants and great views.

3. See the dinosaurs at the Field Museum of Natural History .

4. Put a life jacket on to kayak the various Chicago river trails. Probably an activity best done in the summer to be honest. 

Want to know what to do in Chicago in winter? 

Watch my video!

And you can check out my YouTube channel for the latest travel inspiration…

5. Become a little starry eyed with a trip to the Adler Planeterium . Check out their website for details of the late night openings.  

6. Learn what it took to create the Chicago skyline with the Chicago Architecture Foundation River Cruise. I have it on good authority that this is one of the coolest things to do in Chicago. Book the architecture tour in advance to guarantee a seat. 

7. Step back in time with a drink and some jazz at the legendary  Green Mill cocktail lounge. This is one of the many trendy things to do in Chicago.

8. Tick a baseball game off your all-American bucket list with a visit to Wrigley Field . And you’ve only really been to the baseball when you have a hot dog in the stalls. 

9. Watch an outdoor movie at Millennium Park . There are often concerts and special events here so make sure to check the listings for your dates.

10. Explore the shops, restaurants and gardens of Navy Pier.  You’ll find Harry Caray’s here, a big ferris wheel and that great American staple, Bubba Gumps. 

Where is Chicago? 

Chicago is in the north of the USA, in Illinois and on Lake Michigan. When I visited the first time I arrived by Greyhound Bus from Nashville via St Louis, which I wouldn’t really recommend to be honest. Too far. After Chicago I went to Minneapolis though, to the north border with Canada, and that was great. 

Second time I just flew in and out of Chicago International Airport which was simple. Do that! 

Or, Chicago is on the famous Route 66, so it’s the perfect stop on a great American road trip too. 

There are some great road trips from Chicago for you to enjoy this year.

More cool things to do in Chicago

11. Take a tour underground in the city’s freight tunnels.

12. Enjoy one of the best cups of Joe at Heritage Bicycles, part bike shop, part coffee house.

13. Check out the world’s largest stained glass Tiffany dome at the Chicago Cultural Center. There’s also an impressive one at Macy’s. 

14. Live out your Grey’s Anatomy fantasies at the International Museum of Surgical Science .

15. How about a guided food tour to really fill you up in Chicago?! So much to eat there you wouldn’t want to miss out. There’s a video of my Chicago flashing up on this page somewhere, if you want to see some of the great food we got on this tour.

16. Then do your downward dog beside some of the coolest cats with a free class of outdoor yoga, pilates or zumba inside the Zoo. There’s a special area for the yoga, looking out to the Chicago skyline. 

17. Garfield Park Conservatory is one of the country’s biggest greenhouses with over 600 species of plants and trees for you to have a gander at. It’s also nice and warm. Just thinking of anyone visiting Chicago in winter – this is a good shout. 

18. Freak out as you look down from 103rd floor of the Willis Tower on the Skydeck . Honestly, it’s amazing the trick it plays on your mind. 

19. Unleash your inner art critic at The Art Institute of Chicago.  There are some incredible originals from well-known artists here – one of the best collections in the world in fact. 

20. Enjoy a lazy Sunday with a bit of bargain hunting at the Maxwell Street Market . Around since 1984, it has some of the city’s finest Mexican food as well as vintage items.

21. Walk the Magnificent Mile and do some window shopping, or if you wanna splash some cash, step right up. 

22. See otters, octopuses, dolphins and penguins at the Shedd Aquarium.

23. Time travel back to the 90s at The Wormhole Coffee where Nintendo and Back to the Future rule.

24. Prepare to wait in line for two hours as you queue for the best tacos and margaritas in town at Big Star .

25. See an old movie or watch a talk with a film director at the Music Box Theatre.  If you can catch it on a good day it’s definitely one of the coolest things to do in Chicago.

26. Explore the world of the Wizard of Oz fans at Oz Park where statues of the characters are dotted about the greenery. Get your selfie on with the Tin Man. 

– Checking out this cityscape is one of the coolest things to do in Chicago IMO

27. Stock up on your spy supplies at Wicker Park Secret Agent Supply Co. and feel good about it because profits go to tutoring kids.

28. From there, keep ticking items off the shopping list with a trip to Woolly Mammoth Antiques and Oddities , which sells objects bought back to life. Apparently the aim of the shop is to help us all feel a bit better about death.

29. Pay your respects to all things pooch poop at the Shit Fountain which serves as a reminder for dog owners to poop and scoop. Definitely one of the more interesting things to do in Chicago!

30. Feel like you’ve actually achieved something by rock climbing at the Maggie Daley Park climbing wall.

31. Pick up a good read at Myopic Books.  Then go and sit at one of the city’s many, many coffee shops to read through. 

32. Or, spend an afternoon with your new book on the urban Ohio Street Beach .

33. Lean 1,000 feet over Chicago’s Michigan Avenue at 360 Chicago with the Tilt experience .

34. Feel a little creepy standing in the exact spot the Obamas are thought to have locked lips for the first time at the Obamas Kissing Rock on 53rd Street and Dorchester Avenue. Do we believe it? 

35. Celebrate the invention of one of the best baked goods, the brownie, at the Palmer House Hilton.

36. Live out your mad scientist dreams at the Museum of Science and Industry.

– Visiting a diner is definitely one of the coolest things to do in Chicago!

37. Get a huge breakfast at Lou Mitchell’s to set you up for the day. It’s the start of Route 66, so get your kicks! 

38. Unwind with a bit of music and comedy at the Phyllis’ Musical Inn .

39. Learn about all things deep crust and cheesy and greasy at the U.S. Pizza Museum.  One of the most calorific and coolest things to do in Chicago. 

40. Afterwards, check out Giordano’s for authentic deep dish Chicago pizza. Or Malnati’s – you need to weigh in and decide on your favourite of the two for future reference. Eating is seriously one of the most important things to do in Chicago. There are so many iconic dishes to work your way through. Take a look at this guide to Chicago specialities by thesavvyglobetrotter for starters.

41. Listen to some of the best live blues and jazz at the oldest blues house in the city, Kingston Mines.

42. In the summer months, try stand up paddleboarding on Lake Michigan.

43. Buy an umbrella hat from Chicago radio DJ Carl Bonafede, apparently you can’t go home without one.

44. Head to Big Joe’s bar on a Friday night to watch a real-life turtle race (it’s a thing). Strange thing to do in Chicago!

45. Take your clothes to be cleaned at Pert Cleaners and wander the Antique Fabricare Museum at the back while you wait.

46. Enjoy a mid afternoon sugar rush at Stan’s Donuts,  or, if you’re up by Lincoln Park, try Firecakes Donuts. They’ve won awards for their sugary delights and I popped in for a try.

– Mmmm donuts. Eat them in Chicago! 

47. See where the likes of Tina Fey and Bill Murray started out with a trip to the Second City comedy complex.

48. Continue your showbiz education at the Museum of Broadcast Communications .

49. Have a drink in a boat come bar looking out at the lake at North Avenue Beach House.

50. Fill yourself up for the day with brunch at the The J. Parker rooftop restaurant.

51. Burn it off by renting a bike and cycling the 18-mile stretch around the lakefront. This is definitely one of the coolest things to do in Chicago as you get a good look around the city. 

52. Find yourself some wheels and visit the Superdawg drive in for one of the city’s best hot dogs.

53. The Gangstas and Ghosts Walking Tour looks awesome. 

54. Or how about an Underground Donut Tour – sounds pretty sweet hey?!

55. The skyscrapers are legendary in Chicago – learn more about them on an evolution of the Skyscraper tour .

56. Say hello to the animals at the Lincoln Park Zoo –  it’s free! 

57. How about driving from Chicago to Atlanta for your next adventure?

Accommodation in Chicago

If you’re looking for accommodation in Chicago, then check out the properties on Booking.com . They have some unique apartments to rent, or you can rent a room in someone’s apartment, to truly get that local flavour. 

I was in Chicago, Illinois thanks to Enjoy Illinois, the Illinois Office of Tourism. I received visits to most of the above in return for a review and a mention in my travel blog. If you’d like to find out more about Illinois,  just click this link .

4 awesome day trips from Chicago 

There’s loads of fun things to do in Chicago, as you’ll have read. Keep in mind though, there are also some great day trips from Chicago too. 

1. Six Flags Great America 

With nine themed areas and 16 rollercoasters, Six Flags Great America is one of their leading theme parks. Over three million people visit every year. There’s also a 20-acre (81,000 m 2 ) water park called Hurricane Harbor to keep you busy. 

Six Flags Great America is in the state of Illinois, just a 50-minute drive north from the city. Buy your tickets in advance to avoid the queues at the gate. 

2. Grand Rapids, MI

Yep, you will have to leave the state but Grand Rapids in Michigan, less than three hours round the lake, could be worth it.

Best seen during summer and fall, Grand Rapids is famed for its breweries, coffee shops and delightful coffee shops, as well as the stunning lake, of course. Try and time your trip with one of Grand Rapids’ festivals to really get the most from your trip. 

3. Holland, MI

Fancy going somewhere a little quirk on your trip to Chicago? 

Well, Holland in Michigan aims to recreate all the European glory of the Netherlands. Celebrating its Dutch heritage there are plenty of Dutch cafes and restaurants to enjoy and even a huge tulip garden in  Veldheer Tulip Gardens  too. Here five million of the eponymous flowers explode into bloom each spring.

There are some great Dutch pubs here, and even a Windmill Island Garden for that authentic Dutch vibe too. 

Holland is 2.5 hours from Chicago and on the way to Grand Rapids. 

4. Lake Geneva, WI

An hour and a half from Chicago, up in Wisconsin, you’ll find Lake Geneva. Known as an idyllic vacation town, Lake Geneva is based on an 8-square-mile body of water made for summertime fun. 

Visit in the summer and you can rent a kayak or a paddleboard, or even try wake surfing. If water’s not your thing then you can trek some of Lake Geneva’s 21-mile Geneva Lake Shore Path. The mansions you’ll come across there will make it totally worth it. 

Lots of nice cafes to choose from here – just take your pick!

Your visit to Chicago

I hope I’ve inspired you to visit Chicago at some point in your life. I feel like I’m cheating on New York when I say it, but I really do think it’s the most interesting city to visit in the USA. 

In third place?

New Orleans for sure . 

More on Chicago

What to Do in Chicago in Winter

Fun Things to Do in Springfield, Illinois

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Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

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As a proud Chicagoan, I wanted to commend you on an amazing list! One thing – Maxwell Street Market dates back to the late 19th century. https://en.m.wikipedia.org/wiki/Maxwell_Street

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12 Coolest Things to do in Chicago You Shouldn’t Miss

Epic Things to do in Chicago – Recommended by a Local!

Traveling somewhere for the first time can be overwhelming sometimes. Usually, there’s just way too much to do and it’s not possible to include everything in the itinerary.

Before my trip to Chicago, a vibrant city in the Midwest , I created a list of all the activities I wanted to do. Let’s just say I was a bit too motivated and enthusiastic because it was enough for a 2-month stay (at least).

Fortunately, I had a friend of mine living in the city who made sure I had the best time there.

To help you plan your trip, I decided to write down the coolest things to do in Chicago for first-timers (and everyone else) – compiled by my friend and me!

(This post contains affiliate links, which means I receive a certain percentage of a sale if you purchase after clicking.)

TIP: Chicago is well-connected to many other major US cities via train so if you want to travel sustainably, book train tickets to Chicago instead of plane tickets!

TIP:  To save up to 50% on all the top attractions in the city, make sure to buy a Chicago CityPASS !

12 Awesome Things to do in Chicago For Everyone!

1. enjoy a 360 degrees view of chicago.

I don’t know about you but one of the first things I love to do in a new city is to find a place high up from where I can enjoy a great view.

Whether that means climbing an old church like in Amsterdam or hiking up a fortress in Kotor, Montenegro.

In this case, it’s taking an elevator up to the 94th floor of the John Hancock building, one of the tallest buildings of the Chicago skyline.

360 Chicago is an observation deck that enables a breathtaking 360-degree view of the city. It even comes with its own bar where you can enjoy a drink while admiring the view.

If you fancy some more action, you can try the TILT – a platform made out of glass and steel.

As its name may already tell, the platform tilts outward , making you lean forward and get a downward-facing view of the Magnificent Mile 300 meters below.

The tickets for the observation deck are a bit more than $30 for adults and if you want to try the TILT you have to pay more than $30 extra.

Paying another $30 for the ride is a bit too pricy in my opinion so you can skip it if you don’t want to spend that much money.

I recommend buying the tickets in advance so you don’t have to queue.

Tours you might find interesting :

2. Do Some Shopping at Magnificent Mile

Another one of the coolest things to do in Chicago is to walk around the city’s most famous shopping area.

The Magnificent Mile is a section of Michigan Avenue and home to luxurious shops, fashion outlets, fancy restaurants, and posh hotels.

Along the avenue, you can spot some famous landmarks such as the Chicago Water Tower, the Wrigley Building, and of course the John Hancock Center.

It’s also the perfect place to do some shopping at one of the three major shopping centers or enjoy some fun activities such as an escape room adventure at the nearby location of The Escape Game .

Fun fact: People living in this area have to dig deep into their pockets. Magnificent Mile is the eighth-most expensive place to live in the US , right behind Fifth Avenue in NYC and Rodeo Drive in Beverly Hills.

Something else you’ll find along the Magnificent Mile and other parts of downtown Chicago is different painted dog sculptures.

All of these sculptures were created to honor police officers killed or injured. Keep your eyes open so you won’t miss any of these lovely German Shepherd Dogs!

3. Have a Drink at LondonHouse Rooftop Bar

How does sipping a cocktail at a rooftop bar while watching the boats floating on the Chicago River sound to you?

If this is exactly your kind of thing to do then don’t miss a visit to the rooftop bar of the city’s best-located hotels.

The LondonHouse Chicago is a 4-star hote l in a 1920s building facing the iconic Riverwalk. From its tri-level rooftop bar , you can take in stunning views of the Chicago River, Magnificent Mile, and even Lake Michigan while sipping a delicious cocktail.

4. Escape The City Life in Millennium Park

During your first time in the Windy City, a stroll through Millenium Park is an absolute must!

This public park is one of the most popular free attractions, mostly because of the famous installation you can find there: Cloud Gate – also called “the Bean” .

Besides the funny-shaped sculpture, Millennium Park is also a great place to escape busy city life.

It’s a wonderful green oasis in the middle of downtown Chicago thanks to places like the beautifully made Lurie Garden .

Moreover, you can marvel at fascinating outdoor art at the Boeing Galleries or enjoy a free music festival at the Jay Pritzker Pavilion.

Even when there’s no show at the pavilion, it’s the perfect place to relax on a blanket, have a picnic, and watch the sun go down.

My friend also told me that Millennium Park is especially worth visiting during Christmas in Chicago . There’ll be an ice rink, carousels, and many other fun attractions!

5. Take a Stroll Along The Chicago Riverwalk

Millennium Park isn’t the only great place to enjoy a walk.

The iconic Chicago Riverwalk enables you to take a leisurely walk along the picturesque river floating through the city.

At first glance, it may appear as just a normal pedestrian waterfront but the Riverwalk is more than that. You can enjoy drinks in different cool outdoor bars or have lunch in one of the many restaurants along the waterfront.

Moreover, you can visit a museum dedicated to the Chicago River or find some pretty awesome outdoor art galleries throughout the trail.

If you’re looking for some more adventurous experiences, do a Chicago River kayak tour or any other fun boat tour .

Whether day or night, the Riverwalk is a unique and vibrant place you won’t find anywhere else in Chicago. I can’t even tell you how often I visited it during my time in the city.

The relaxing and fun vibe made me fall in love with this place so much and spending some time there is definitely one of the best things to do in Chicago!

6. Explore The Hip West Loop Neighborhood

The next place you should check out is probably a bit different than what you expect to find in the city.

Formerly an industrial zone, West Loop is now a popular neighborhood known for its great dining and nightlife scene. Thus it’s one of the coolest neighborhoods to stay in Chicago !

Once warehouses, most of the buildings in West Loop are now home to some of Chicago’s top restaurants. Especially Fulton Market is now a popular area for many locals thanks to its hip industrial vibe.

The range of restaurants or cafés is immense and one place I can highly recommend is Sawada Coffee .

This edgy coffee bar inside a graffitied building is the perfect address to get a good cup of your daily dose of caffeine. If you’re not a coffee drinker, try their special Matcha Latte creation called “Military Latte” – you’ll love it!

7. Spend a Relaxing Evening at Noyane Rooftop Bar

Admittedly, it’s really hard to beat the LondonHouse rooftop bar, and especially the view from up there. However, another awesome one you should visit is Noyane on the rooftop of Conrad Chicago .

It may not be able to keep up with the LondonHouse rooftop views, but the ambiance is at least as good – if not better.

You’ll find modern furnishing, a cozy fire pit, and a large bar area where you can order almost any kind of drink you want.

If you get hungry, don’t hesitate to try some of the high-class dishes of the Japanese-Peruvian restaurant .

8. Ride The Ferris Wheel at Navy Pier

For the next point on the list, it’s time to leave the inner part of the city and head in the direction of Lake Michigan. There you can find Navy Pier, a 1-km-long pier on the shoreline of the lake.

You can easily spend an entire day at this pier because there are so many fun outdoor attractions .

A sensory maze experience, a botanical garden, a Musical carousel, and the Chicago Children’s Museum are only some of them.

In the center of the pier and hard to oversee is the Chicago Ferris Wheel. This 60-meter-high construction offers some of the best skyline views while rotating at a gentle speed.

Tickets for single rides are $12 for children and $20 for adults. It’s definitely not a cheap pleasure but it’s a lot of fun and it’s great to see the city skyline from the lake.

If you want to skip the line, you can buy online tickets in advance .

TIP:  The best is to buy a Chicago CityPASS to save up to 50% on all the top attractions!

9. Wander Around Old Town & Visit Its Most Beautiful Café

At least since I mentioned West Loop you know that Chicago doesn’t only consist of skyscrapers.

There are so many other different areas besides downtown that are totally worth exploring and one of them is the gorgeous neighborhood of Old Town.

Thanks to its Victorian-era buildings, Old Town kind of looks like a town you could find somewhere in Britain. It’s an area popular for its quaint streets, small shops, old-school pubs , and artisanal cafés.

One of these coffee shops, and also one of the best places for breakfast in Chicago , is the 3 Arts Club Café inside Restoration Hardware – a home furnishing company.

The first time I entered I was utterly speechless as I’d never seen such a beautiful café before.

Crystal chandeliers hanging from a glass ceiling, a fountain in the middle of the room, and plants in every corner made it look like a wedding venue.

Frankly, it wouldn’t have surprised me if a coffee cost $20 but luckily it wasn’t that expensive! 😀

Sitting beneath those mighty chandeliers with a good cup of coffee – or Chai Latte in my case – is definitely one of the coolest things to do in Chicago!

10. Look Down at The City From The Willis Tower Skydeck

The next activity is definitely not for the faint-hearted or people with a fear of heights.

Chicago has many tall skyscrapers such as the John Hancock Center and the Trump Tower. But the one that surpasses them all is the Willis Tower.

This more than 440-meter-high skyscraper was built in 1973 and after its completion, it was the tallest building in the world for almost 25 years.

On the 103rd floor, there’s an observation deck called “the Skydeck” . To get there you have to take an elevator that reaches the top within only 60 seconds.

During the ascent, you can literally feel the change in pressure which might be a bit frightening.

Once you reach the 103rd floor, you’ll quickly find out why the Skydeck is one of Chicago’s most famous attractions.

Of course, most people come here to admire the stunning view but there’s something else to experience.

Since 2009, it’s possible to see the city from a completely new perspective thanks to glass balconies extending more than one meter from the facade.

As soon as you step into the glass boxes, you’ll be able to see cars driving in the streets right beneath your feet. It’s a really crazy and a bit of a scary feeling to kind of “stand above” the city.

Also, don’t forget to take some cool pictures there because the Skydeck is definitely one of the best Instagram spots in Chicago !

Tickets for the Skydeck start from $36 and it’s best to buy them online in advance.

11. Eat Your Way Through Chinatown

You can find it in New York City, Los Angeles, San Francisco, and of course in Chicago as well. Yes, I’m speaking of Chinatown!

It’s the third and last neighborhood whose visit needs to be included in my list of the coolest things to do in Chicago.

This neighborhood is probably the most dynamic and tasty one in the entire city.

You can eat your way through regional restaurants, small eateries, and dim sum spots , or have a soothing cup of hot tea at one of the many authentic teahouses .

If you’ve had enough food, it’s time to dive a bit deeper into the heart of this neighborhood.

The best address for this is the American Museum of Chicago where you’ll learn more about the experiences of Chinese immigrants.

12. Admire The Skyline From North Avenue Beach

Last but not least, make your way to North Avenue Beach – one of my absolute favorite places in the Windy City.

North Avenue Beach is one of the city’s most popular public beaches and is located in Lincoln Park. In summer, it’s a hotspot for swimmers, sunbathers, and volleyball players.

Even during other seasons, its lakeshore path is usually filled with rollerbladers, bikers, or people enjoying a casual stroll.

My friend and I went there twice and every time I was overwhelmed by one thing: The breathtaking skyline view.

The first time we came here during the day and on my last evening, we decided to go back and watch the sunset .

I can still remember the moment it got dark and I sat there admiring the bright skyline reflection on the water.

I don’t know how much time passed but suddenly a runner came by and stopped not far from me. First, he looked at the skyscrapers, then turned around and said: “Isn’t it beautiful”? .

The only thing I could answer was yes because I was just so overwhelmed by my emotions. I felt so happy yet so sad as I had to leave this awesome city the next day.

This moment was definitely one of the most special ones I ever experienced in my life. It was the perfect ending to an amazing time in the city and I hope you’ll find Chicago as great as I did!

Find Accommodation in Chicago:

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Do you want to travel like me? Here are some of my favorite travel tips and resources:

Flights: I prefer using CheapOair or Skyscanner to book flights. The destination everywhere feature is perfect for finding some cheap deals! Accommodation: Booking.com is my favorite site to find some great hotel deals. I do love staying at a local place as well, thus I book an Airbnb every now and then. Travel Insurance: There are many reasons why travel insurance is important and I never travel without one. I use the simple and flexible one from SafetyWing that protects me against unforeseen events. Tours: I love taking tours to explore destinations like a local. My favorite website to book them in advance is GetYourGuide . Camera Gear: I use a Nikon D5300 camera with an 18-105 mm and a 10-20 mm wide-angle lens to take my photos.

Hey and welcome to my blog! I’m Alina, an Austrian travel addict and vegan food lover who has a passion for exploring new destinations and trying out the best plant-based food around the world. Come and join me as I share exciting bucket list experiences and provide helpful travel guides for your own adventures!

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68 Comments

These are a great places to visit!

Yeah and there’s even so much more to see!

Wow, Chicago looks so amazing! ♥ I am dreaming one day to fly to the USA and travel throughout every state! I hope I will then visit Chicago too!

It’s a cool city! I hope you can make it there soon 🙂

This is such a great article! I will definitely come back to it if I ever make it to chicago!

Glad you like it 🙂

This is amazing Alina! I really need to get back to Chicago. I went a few years ago for a work trip, but I unfortunately didn’t get to experience it the way I wanted to. I will totally keep this handy for when I go back, which is hopefully soon. I definitely want to get to that rooftop! 🙂

I’ve never been to Chicago, but it looks so good 🙂 I need to add it to my travel bucket list. Btw, I love your pictures too!

Thanks a lot Cristina ☺️

Chicago looks great! I really want a photo next to the Bean, and a view from a rooftop bar. Thanks for sharing.

It’s such a cool city ?

I didn’t know there’s a wheel in Chicago as well! Looking forward to visit it one day! 🙂

It’s a really cool city! 🙂

I’ve never been to Chicago before despite living in the US for years and this is an amazing first-timers guide, the activities all look so cool, especially the stroll along the riverwalk! Thanks for this, definitely keeping it handy for the future 🙂

It’s such a cool city, I enjoyed my time there so much! Hope you can go there someday Jiayi 🙂

I’m trying to decide whether Chicago has been an up-and-coming hot destination to visit or have I just been missing out this whole time!? Haha.

Hahaha it’s definitely a really cool city! 😀

I have never been to Chicago, but it looks like such a vibrant, bustling city! One day I would love to visit.

Oh yes it definitely is! I hope you can go there one day 🙂

On last visit to USA I couldn’t visit Chicago, keeping this list handy for my next visit.

I hope you’ll be able to go there soon!

Some great ideas for things to do in Chicago! I really liked the city, nice vibe. There are definitely some things on this list I would like to try when I return

Yeah it’s such a hip city!

Chicago looks AWESOME! I hope I get to visit it in the future!

It is! Seriously such a cool city ?

There are so many awesome things to do in Chicago that I didn’t know about! Chicago is now well-and-truly on my bucket list for US travel, thank you!

Yaaay! It’s really an awesome city 🙂

How awesome! I visited Chicago last year and I loved so much! You just brought back a lot of nice memories Alina! Thanks for sharing!

I can remember you visited Talia! 🙂 I’m happy you liked it as much as I did

Chicago is such a cool city, can’t wait to visit once! I’m absolutely obsessed with the SkyDeck, the view is just wow! 🙂

It’s truly an awesome city to see!

Wish I had read this list before I visited Chicago! Definitely saving it for whenever I go back. Also I’d recommend visiting Aire Ancient Baths, specially in the cold winter! We did and it was the highlight of our trip <3

Oh never heard of it! Need to do it next time I’m there 🙂

Wow! So many cool things to do there! I visited Chicago many years ago for just 1 day of a cross country road trip. I would love to go back. The Riverwalk and Old Town look wonderful. I’d love to do a boat ride on the river too. Thanks for sharing all these great tips. I pinned this.

Yeah there’s a lot to do! Happy you like it 🙂

Great pics! Chicago looks pretty cool, I would love to visit.

It’s an amazing city ?

Great list for a great city! I would add to visit a live music club. There are some fantastic ones in Chicago – for blues or jazz or pretty much anything!

Oh yes that’s a good idea!

Chicago looks amazing! and there is so many interesting things to do too. What an interesting place. Hope I can go there someday 🙂

It’s such an awesome city!

Chicago has been on my bucket list for so long! I can’t wait to visit! Old Town look beautiful, I’d love to explore it! And I’d definitely want to admire the view from the Willis Tower Skydeck – what a great way to see the city! Thanks for the great guide!

Happy you like it Hannah! I hope you’ll make your way to the city soon 🙂

I really need to visit Chicago again. The only time I’ve been was in January for a work trip and although I did a couple of fun things it was also way too cold. I really should have done the 360 view though, and some of those bars look so nice

Oh I can imagine it being cold that time of the year! I hope you can go there again 🙂

Chicago is most definitely still on my list of cities to visit. I think it’s that combination of tall skyscrapers and the winding river that attracts me. I’ll make sure to keep this article in mind when I can visit. Thanks so much for sharing!

Yeah I totally know what you mean! Such a cool combination 🙂

Reading this reminded me of my trip to Chicago 10 years back . Somethings look just the same. But need to visit back for Millennium park and so much more. Thanks for sharing.

It’s such a cool city isn’t it?!

I loved Chicago. Thanks for bringing back nice memories about this awesome city. I hope to visit it again someday.

Happy you like it!

I’ve never been to Chicago before, but I hope to in the future! I love visiting unique places when I travel so thanks for the tips!

Fingers crossed!

This is a great guide! I spent lots of time in Chicago as a kid, but I would love to return to experience the city as an adult. I think I would love to go shopping at Magnificent Mile and enjoy a drink at the LondonHouse Rooftop Bar. Thanks for putting this guide together. Also, your photos are lovely! 🙂

Happy you like it Brittany 🙂 Chicago definitely is worth going back!

This is where I’m from! I love Chicago and this is a great list. I’d also recommend one of the many amazing museums next time you’re there and have more time 🙂

Oh wow you grew up in an amazing city!

Ahhh, this post came at just the right time because I’m going to Chicago next week! I’m a sucker for seeing a city from above – it’s the one thing I try to do in every city that I visit. I’ll definitely have to check out the Skydeck or 360 Chicago!

Oh wow awesome! I wish you an amazing time in Chicago! 🙂

This Chicago guide is incredibly helpful. You’ve really thought through everything you need to know before planning a trip. Thank you for this helpful resource. Saving this guide for later!

Happy you find it helpful! 🙂

You give some great advice here. I adore the artsyness of the West Loop. It’s great for spotting street art and getting great mural pics.

Yes! West Loop is one of my favorite areas 🙂

Such a great list! There’s so much to do in Chicago and I’ll definitely leverage this on my next visit.

Happy to hear this!

very perfect article, thanks for sharing it with us.

This is wonderful blog I have gone through it, Good Informative searching for a long time Looking forward to visit Chicago with family members for a long weekend. Thank you alot.

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USA TODAY 10Best

Readers' picks: An essential guide to the best things to do in Chicago

May 2, 2024 // By Jacky Runice

By Jacky Runice Travel Journalist May 2, 2024

I fancy myself a Chicago know-it-all (lifelong Chicagoan, radio host, journalist, nosy neighbor), but just about every Chicagoan feels the same.

This guide highlights the USA TODAY 10Best Readers’ Choice Award winners of Chicago, from awesome restaurants and bars to the greatest hotels, events, and activities in this world-class town.

Chicago has been voted among the top 10 for Best Beer City , Most Walkable City in the U.S. , and Best Summer Destination , among others — all for good reason!

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Bookmark this list for your next trip to Chi-town.

Best hotels in Chicago

Voted one of the Best New Hotels in the U.S., The St. Regis Chicago is one of the city’s many architectural marvels, designed by award-winning architect Jeanne Gang. The property includes premier butler service, nightly champagne sabrage, and The St. Regis Spa , one of Chicago’s wellness meccas.

The hotel is home to two of Chicago’s finest restaurants: Tre Dita , a love letter to Tuscan cuisine, and the airy and light-filled Miru .

Insider tip: The hotel’s rooftop terrace overlooks the city with bird’s-eye views of fireworks at Navy Pier (crowned the Best Place to See Fireworks .)

The Peninsula Chicago Hotel is an extraordinary place to roost. Z Bar, Pierrot Gourmet, and Shanghai Terrace beckon with warm weather terraces and stellar food and beverage. Afternoon tea service in The Lobby is especially festive during the holidays when the hotel does it up with live music, extravagant decor, ice skating, and spectacular overnight packages. Those are just a few reasons readers voted this establishment among the best hotels for the holidays .

Need relief from the buzz of the city? Book a seasonal treatment at Leaf Spa at Fairmont Chicago Millennium Park , voted one of the best hotel spas in the country.

Environmentally minded visitors go for the LEED Gold-certified Virgin Hotels Chicago , voted one of the country’s best eco-friendly hotels .

The Publishing House , which has earned a 10 best ranking for Best Bed and Breakfast , will completely change the minds of travelers who don’t think they like bed and breakfasts, thanks to the chic decor, laid-back ambience, and outstanding breakfast near Chicago’s Restaurant Row.

Readers voted SOPHY Hyde Park as a Best Boutique Hotel . The South Side vibe combined with the hotel's smart rooms, artistic indoor, and outdoor spaces complements the cultural essence of the neighborhood that the Obamas once called home.

Best Chicago restaurants, cafes, and sweet shops

When that midafternoon snooze hits, sip a phenomenal cup of joe at Big Shoulders Coffee , a Best Independent Coffee Shop winner. With a former chef-turned-coffee roaster at the helm, stop here for no-nonsense artisan beans, roasted to perfection.

There are handmade candies galore at Windy City Sweets , a 2023 winner for Best Candy Store , from nostalgic treats to signature, homemade fudge, s’mores, and more. At Katherine Anne Confections , which got a nod for Best Chocolate Shop , you’ll find seasonal flavors plus classics like salted caramel.

Stock up on bakery goods or enjoy biscuits and gravy and two-fisted sandwiches at Wheat's End Cafe , one of the best gluten-free bakeries in the country.

In a city that takes its pizza seriously, both Chicago’s Pizza and Robert’s Pizza and Dough Co. made the top 10 for best gluten-free pizzerias for their in-house crusts and array of toppings.

The Oakville Grill & Cellar , one of 2024’s best new restaurants, has a great happy hour and weekend brunch. Featuring ingredients from farms and ranches across the Midwest, enjoy menus for lunch and dinner on the all-season patio.

Chicago has a plethora of notable steakhouses, and Asador Bastian , a Basque-inspired chophouse in River North's Gallery District, is something really special. Another Best New Restaurant winner, here you'll enjoy several varieties of flame-kissed beef, seafood, and a tortilla Española that will whisk you right to San Sebastian, Spain.

Traveling to or from Chicago? Don’t overlook the restaurants at O’Hare Internationl Airport , one of the best airports for dining . Notable stops include Rick Bayless’ Tortas Frontera, Berghoff Cafe for German items, cheeseburgers at Billy Goat’s, or Gold Coast Dogs for Chicago-style hot dogs and Italian beef sandwiches. For drinks, hangout at Goose Island Beer Company or Publican Tavern.

Best Chicago bars

With more than 160 Chicago breweries capturing the imagination and outsider appeal of craft beer culture, this Best Beer City continues to bag a barrel-full of awards.

Pilot Project Brewing , a springboard for startup breweries bringing exciting new brews from around the world, and Sleeping Village are both award-winning beer bars . Visit the Pilot Project Brewing’s incubator and taproom to sample beer, craft non-alcoholic brews, tea, and coffee.

Among 2024’s best new breweries , Black-owned Funkytown Brewery brings diversity to the craft brew space, winning multiple awards for suds like Hip-Hops, R&Brew, and Cuffin’ Season. Also voted a Best New Brewery by USA TODAY 10Best readers: Turner Haus, a Black, family-owned enterprise in Bronzeville. They brew and name beers after the family matriarchs.

Readers voted Chicago’s first botanical brewery and restaurant, Forbidden Root , as a Best Brewpub for its continuously rotating menu of Midwestern food and beverage tweaked with the seasons. Another Best Brewpub: Old Irving Brewing Company .

Don’t miss women-owned ERIS Brewery and Cider House , which topped the list as Best Cidery in the country.

Best events in Chicago

Chicago teems with festivals. Windy City Smokeout, an outdoor country music and BBQ festival, was a winner of the Academy of Country Music Awards' Festival of the Year, as well as a USA TODAY 10Best Readers’ Choice Award for Best Specialty Food Festival . Count on an impressive lineup featuring some of country music’s biggest names, along with the ultimate BBQ and craft beer from around the country.

A Chicago tradition since 1980, the Taste of Chicago thrills locals and visitors who want to experience Chicago’s expansive food scene, peppered with live music, entertainment, and family fun. The free-admission event takes place over three days in Grant Park. Chicagoans don’t mourn the end of festival season when the first leaves float off trees; they just keep partying!

The Chicago German-American Oktoberfest is a wunderbar Best Oktoberfest filled with music, dancing, and lots of wurst, pretzels, and beer.

The Magnificent Mile Lights Festival winds down Michigan Avenue and up to a top 10 spot on the Best Holiday Parade list. Stroll over to Christkindlmarket , the award-winning German-style bazaar that will fill you with holiday cheer.

Best attractions and other things to do in Chicago

Whether participant or fan, the Windy City has a roster of activities for sports fans year-round. One of two classic historic ballparks still standing in the U.S., Wrigley Field , clutched a spot as one of the best MLB stadiums . The 1914 ballpark has modern amenities, from a sensory room to electric vehicle charging stations. Don’t miss iconic Chicago snacks like Garrett Popcorn, Home Run Inn pizza, Vienna Italian beef, and Anthony Bourdain’s favorite, Hot Doug’s.

When the dogs start barking, get off of your feet and onto Chicago’s First Lady Cruises , a Best Boat Tour winner, an ideal way to see iconic architecture, or settle into a kayak to paddle the Chicago River.

This city has numerous must-visit institutions, like the internationally admired Art Institute of Chicago . This Best Art Museum is rife with Hoppers, Picassos, Van Goghs, and O’Keefes.

The most popular exhibit every year at the National Museum of Mexican Art is for the Day of the Dead. The museum dazzles with gleaming altars, whimsical sugar skull sculptures, and eye-popping art celebrating the dearly departed in colorful ways that are anything but grim. It ranks as one of the best free museums in the country.

Brush up on your science smarts and feel the physics at the massive Museum of Science & Industry , the largest science museum in the Western Hemisphere and a winner for Best Science Museum in the country.

Since Chicago was deemed one of the most walkable cities in the U.S. , you can easily torch some calories at the city’s first elevated park, The 606 ; the 18.5-mile Lakefront Trail ; walking paths at Millennium Park ; or just tooling around the neighborhoods.

About Jacky Runice

Born in Bucktown when bulletproof was a home safety choice and not a coffee order, Jacky Runice has been knocking around Chicago as a professional print, online and broadcast journalist and editor specializing in separating the riff from the raff in culture, entertainment, food, travel and pure unadulterated fun. Jacky is a member of the International Food, Wine & Travel Writers Association (IFWTWA). In her best Chicagoese, Jacky asks, "Who has the time or money to blow on hotels, attractions, restaurants, exhibits and activities that blow?"

Read more about Jacky Runice here.

Connect with Jacky via: Website | Facebook | Instagram | Twitter | Pinterest

Chicago architecture: 12 iconic buildings not to miss

Last updated on July 19, 2023 by Choose Chicago

Chicago is a city of firsts — and nowhere is this better seen than in our architecture. The city’s ground-breaking structures include the first-ever skyscraper (the now-demolished Home Insurance Building, completed in 1885), a UNESCO World Heritage site designed by Frank Lloyd Wright, and a skyline made of the world’s most iconic buildings.

Here are 10 history-making examples of Chicago architecture, and the many reasons why you should pay them a visit.

1. The Rookery Building

Listed on the National Register of Historic Places, The Rookery Building is located in Chicago’s downtown Financial District. It was designed by famed architectural partners Burnham and Root and was considered one of the world’s grandest buildings when it was completed in 1888. Inside, the winding iron staircase is a must-see.

Another striking feature of the interior is the Light Court. Frank Lloyd Wright redesigned the striking two-story skylit lobby in 1905, recasting it in his signature Prairie style. This is the only project Wright worked on within the downtown cityscape, making it a must-see when you’re in the area.

209 S. LaSalle St., architects: Daniel Burnham & John Root/Frank Lloyd Wright

2. Chicago Cultural Center

Across the street from Millennium Park, the “People’s Palace” opened in 1897 as the first permanent home for the Chicago Public Library. In 1991, it was rededicated as the Chicago Cultural Center and became the nation’s first free municipal cultural center, hosting concerts, art exhibitions, and other programming throughout the year.

Listed as a Chicago Landmark and on the National Register of Historic Places, the massive building was designed in the Classical Revival style, taking inspiration from the monumental structures of ancient Greece and Rome, and the finely detailed buildings of the Italian Renaissance.

Step inside to admire the lobby’s intricate mosaics of glass, gold leaf, mother of pearl, and precious stones. In Preston Bradley Hall, gaze up at the luminous 38-foot-diameter dome, the largest Tiffany glass dome in the world, containing approximately 30,000 individual glass pieces.

Want to dive deeper? The Chicago Cultural Center offers free guided tours that are open to the public.

78 E. Washington St., architects: Shepley, Rutan and Coolidge

3. Wrigley Building

The riverfront Wrigley Building draws inspiration from Spain’s Seville Cathedral combined with French Renaissance details. The building is made up of two towers of differing heights connected by walkways, all clad in glazed terra-cotta.

The gleaming white exterior was inspired by William Wrigley’s visit to Chicago’s World’s Columbian Exposition in 1893, known as the White City.

The building is one of the most recognizable along The Magnificent Mile, sitting proudly on Michigan Avenue along the banks of the Chicago Riverwalk , an award-winning, pedestrian-friendly walkway.

400 N. Michigan Ave., Graham, Anderson, Probst & White​

4. Tribune Tower

Standing across from the Wrigley Building, the soaring Tribune Tower was born from a competition held by Chicago Tribune  to design “the most beautiful building in the world” for the newspaper’s new headquarters.

New York firm Hood and Howells beat out over 250 concepts with its Gothic Revival design, featuring limestone walls, elegant buttresses, intricately carved stonework, and Art Deco touches. The building’s crown was inspired by Medieval European towers, like the 13th-century Rouen Cathedral in France.

In keeping with the concept of borrowing from the past, the Tribune Tower’s facade incorporates some 150 fragments from historic buildings and sites, including the Winter Palace in Beijing, Westminster Abbey in London, the Great Pyramid in Giza, The Great Wall of China, and the Parthenon in Athens.

435 N. Michigan Ave., architects: Hood and Howells

5. Willis Tower

Formerly known as the Sears Tower, the Willis Tower is the city’s tallest building and the second tallest structure in the Western Hemisphere.

The Willis Tower soars above downtown Chicago, standing tall at 110 stories (1,450 feet). The building, known for its black and bronze facade, is composed of nine separate “tubes” that strengthen the structure as a whole and rests wind load. This innovative design was completed in 1973, ushering in a whole new era of skyscrapers.

Take in the breathtaking views from Skydeck Chicago on the building’s 103rd floor. The observation deck is home to The Ledge, a series of all-glass bays that extend from the building to provide visitors with unobstructed views of Chicago and the ground below — 1,353 feet straight down. In addition to The Ledge, the new Skydeck experience features museum-quality interactive exhibits.

233 S. Wacker Drive, architects: Skidmore, Owings & Merrill

6. Robie House

In Hyde Park, the Robie House is a hidden gem that’s one of the finest existing examples of Frank Lloyd Wright’s signature Prairie style. Considered a masterpiece of modern architecture, the home is listed as a UNESCO World Heritage Site. Built in 1910, the Robie House underwent a comprehensive restoration to reveal Wright’s original vision.

Take a guided tour to learn more about the visionary design. Public and private tours are available of both the exterior and interior of the home.

5757 S. Woodlawn Avenue, architect: Frank Lloyd Wright

Covering two city blocks and rising 25 stories above the Chicago River, theMART (originally called The Merchandise Mart) was the largest building in the world when it was completed in 1930. With more than four million square feet of floor space, the commercial building is so large that it previously had its own dedicated ZIP code.

Today, TheMART is home to Art on theMART , the largest digital art projection in the world. The first-of-its-kind display features a curated series of digital artworks projected across 2.5 acres (the equivalent of two football fields) of theMART’s river-facing facade every night from April through December.

222 N. Merchandise Mart Plaza, architects: Graham, Anderson, Probst and White

8. Marina City

If the Marina City towers look familiar, it may be because they’ve been featured prominently in pop culture, from movies to TV shows to album covers, since the one-of-a-kind design first debuted in 1963.

Located along the main branch of the Chicago River, this designated Chicago Landmark’s distinctive design features two cylindrical towers that bear a striking resemblance to corn cobs. At the time of its opening, it was the tallest residential building and the tallest concrete structure in the world.

When it opened in 1967, it was touted as a new vision of urban living, with amenities like a theater, gym, swimming pool, ice rink, bowling alley, marina, retails, and more.

300 N. State St., architect: Bertrand Goldberg

9. 875 N. Michigan Ave.

One of the world’s most recognized skyscrapers and an iconic example of late-20th century Chicago architecture, 875 N. Michigan Ave.   was born from groundbreaking engineering that helped to make buildings taller than 100 stories a new possibility.

Breaking from the traditional rectangle shape of most skyscrapers, the structure’s signature X-shaped bracing helps support its towering height (1,127 feet). Its tapered shape was designed to create smaller residential floors on the higher floors, thus allowing for more windows with better views.

Head to the 360 CHICAGO observation deck, located 1,000 feet above the famed Magnificent Mile, for panoramic views of the Chicago skyline and Lake Michigan. If you dare, try TILT, an enclosed moving platform that literally tilts you over Michigan Avenue from the 94th floor.

875 N. Michigan Ave., architects: Skidmore, Owings & Merrill

10. One Illinois Center

One Illinois Center is one of Mies van der Rohe’s final designs, rising above a former rail yard and the site of Fort Dearborn. It is notable as an example of the International Style, marked by an emphasis on volume, with the use of planes of glass versus brick or stone, and a focus on the elegance of materials and technical perfection over applied ornamentation.

Fittingly, the landmark building houses the Chicago Architecture Center , a cutting-edge museum that incorporates striking and immersive exhibits on architecture’s past, present, and future, all with views of the nearby Chicago Riverwalk, Wrigley Building, and Tribune Tower.

111 E. Wacker Drive, architect: Mies van der Rohe

11. Aqua Tower

Bridging the gap between skyscraper and sculpture, the Aqua Tower is inspired by the movement and qualities of water. This shimmering multi-use edifice includes the luxury Radisson Blu Aqua Hotel .

The design of the 80-story tower connects strongly with the outdoors, with individual terraces (each unique in size and shape) that give the exterior it its distinctive undulating appearance. Designed by one of Chicago’s star architects, Jeanne Gang, the building fittingly sits near the city’s lakeshore.

225 N. Columbus Dr., architect: Studio Gang Architects

12. The St. Regis

One of the newest additions to the city skyline, The St. Regis Chicago is the city’s third tallest building and the tallest building in the world designed by a woman. The curving multi-colored glass exterior wraps around the building’s 87 stories, home to luxury residences, a high-end hotel, and various fine dining. It’s a jaw-dropping addition to an already-iconic cityscape.

363 E. Wacker Drive, architects: Jeanne Gang of Studio Gang Architects

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Tribune Tower

The Magnificent Mile

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Willis Tower

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The Most Fun Dinner Spots In Chicago

photo credit: Veda Kilaru

Adrian Kane, John Ringor, Veda Kilaru & Nick Allen

February 29, 2024

Those seeking a polite meal, click away now. This guide is reserved for anyone who’s wondering, “Where’s the place to be?” and might have a penchant for mid-dinner photoshoots and post-dinner bar hopping. Chairs aren’t just for sitting in some of these restaurants and, while food is important, a good time takes priority. They range from new spots flooding your feeds to classics where successful meals are determined by how many Old Fashioneds you drink with your server. These places may not all be the best new restaurants in town, but you'll always walk out with a story or two.

photo credit: Garrett Baumer

Brasero seems to specialize in throwing a party every night. This Latin American spot in West Town is great for upbeat get-togethers of all sizes, with a mix of shareable dishes like fried quail and grilled half lobster, and catchy Bossa nova music that practically begs you to show up with the best gossip to match the secluded space and good-times vibe. But Brasero’s food is equally fun, with nearly everything nailing a balance between sweet and spicy. The moqueca has the perfect amount of chili to enhance the coconut broth, mahi mahi, and shrimp. Whatever you order, you’ll all leave with a light cologne of smoke, thanks to the wood-fire grill in the back and dessert sparklers that constantly float around.

Costera Cocina Tulum

Fulton Market

If the pounding bass-heavy music bleeding onto the Fulton Market sidewalk indicates anything, it’s that Costera likes to party. The liberal use of straw, palm trees, and basket lights leans into its Tulum theme, while the dim lighting and loud DJ sets prove that it’s taken Clubstaurant 101. You’re not really here for the food—it ranges from just fine tacos to tableside flamebéed al pastor that fizzles out into a jammy disappointment. Stick to the drinks and those tacos or a quesadilla (they’re the least offensive). And if you’re here past 11pm on the weekends, it gets even livelier as bottle service starts and airplane-shaped trays full of shots and sparklers fly around.

photo credit: Kim Kovacik

Borscht is warm. Borscht is comforting. Borscht is also fun when you’re at Anelya. This Avondale Ukrainian spot is exciting before you even take a seat. Servers zip around with sparkling zakusky carts full of appetizers. Upbeat electronic music hums in the background while flower-like lamps give the dining room a trippy colorful glow. Once you’re ready to order, servers hype up the menu like they’re narrating a sizzle reel full of haluski and kovbasa. And you will, too. Everything is delicious—from the aforementioned beet soup with poached pears and duck to creamy varenyky stuffed with potato and pork jowl.

photo credit: Jack Li

Best New Restaurants

Provaré is a blast. This bright Italian and Creole spot has an R&B playlist that will remind you of the greatness that is '90s Usher, complimentary shots as soon as you sit down, and food that makes you put your hand up to silence the table so you can have a private moment with the housemade pasta. There are standout dishes like fried lobster tails, creamy chicken parmesan that’s the antidote to your scary Apple news feed, and juicy lamb chops that go perfectly with a side of spicy charred corn. The restaurant is busy but never chaotic, and there’s a good chance the chef will come out to drop off plates and make sure you’re having a good time.

Limited hours. No reservations. An unpredictable menu. We normally consider all of these red flags—but we’re here to tell you that the line out the door is worth the wait. And since they're open until 2am, that wait can be a pretty long one. The menu changes every day, which is both exciting—" This ramp pasta is incredible! "—and bittersweet—" Will I ever see these miso butter scallops again? " Warlord is playing hard to get, but that only makes us want this spot even more.

photo credit: Matthew Reeves

A quick online search of Adalina will show you a sea of white tablecloths and a menu full of pasta and veal chop Parmigiana. You won’t realize how fun Adalina is until you’ve spent a few minutes at this upscale Italian restaurant, sitting on crushed velvet chairs and surrounded by flower paintings that would make Georgia O’Keeffe suspicious. The bar is filled with people hanging out two hours before (and after) their reservation time, and the posh dining room gets louder and louder through the course of your meal. People from different tables will inevitably start to mingle with each other, someone might topple over in their heels, and generally things devolve into a good-natured sh*tshow.

photo credit: Christina Slaton

Maple & Ash

There’s nothing understated about Maple and Ash. It has chandeliers, candelabras, and an optional $200 tasting menu called “I don’t give a f*ck,” where the kitchen decides what you eat. It’s a great restaurant that’s surprisingly versatile—it can support a large group or a quiet dinner for two. This is where you should eat when an occasion calls for going all out, and you want to do so in a space that feels kind of like the mansion from Bram Stoker’s Dracula . The one from the ‘90s with Keanu Reeves and Gary Oldman’s hairstyle that looks like a butt.

photo credit: Allison Gallese

Lakeshore East

This guide exists specifically for places like Miru—and let us count the ways. This Japanese restaurant is on the rooftop of the $700-a-night St. Regis Hotel in Lakeshore East. The view of the skyline is incredible, and the service is even better. The food isn't amazing (the long menu ranges from just-OK sushi to not-very-good entrees like burnt miso cod), but great food isn't why you're here. It's to admire the view, have some drinks and dessert, and feel like you can afford to throw money off said rooftop.

This Greek Restaurant in the West Loop is the size of a football stadium, crowded, plays loud music, and has dishes that pop up regularly on TikTok. 10pm reservations are coveted because at midnight they pass out white napkins for everyone to twirl around, servers come out singing and waving sparklers, and the entire restaurant turns into a club. While some of Lyra’s menu can be hit or miss, the flaky spanakopita and tender lamb ribs are delicious enough to help you forgive the restaurant’s flaws, especially if you love pyrotechnics and being surrounded by an absurd amount of wicker lampshades.

photo credit: John Ringor

River North

Eating at Ummo feels like hanging out in a friend’s loft apartment—if your loft-owning (or potentially squatting?) friend also made fresh pasta. Colorful, framed posters cover every inch of the walls, while energetic funk and soul music fuels the open space. And that excitement carries over to the food. Couples are enthusiastically breaking open a playful tomato-shaped dessert full of raspberry compote, or splitting tasty bowls of lobster ravioli. At a larger table, another group is kicking off the night with dry-aged steak drizzled with tangy bagnetto verde. And when you throw in a second floor with a DJ, pool table, and lots of couches for lounging, there’s no reason the party has to stop after the cacio e pepe.

This Italian steakhouse on the edge of Fulton Market is working hard on channeling mid-century-era glamour, complete with servers in jackets and a humidor. But Fioretta delivers on style and substance. There are excellent steaks on the menu—like an olive-fed wagyu New York strip that will have you wondering whether that cow got to fly on a private jet with a weekend stopover in Portofino on its way to Chicago. Strong drinks and live music on the weekend contribute to the buzzy vibe and make this spot great for a special occasion dinner .

Any Chicago restaurant associated with the words “West Loop,” “Italian,” and “Boka Restaurant Group” is probably going to be a good time. This is the case with Alla Vita, an Italian spot on Randolph. It’s designed to be a crowd-pleaser, buzzing with everyone from couples to large groups in town for some conference. It’s also pretty, decorated with hanging plants and an intriguing overhead installation that looks a little like fish gills. And while the menu isn’t going to blow your mind with creativity (it’s mainly pizza, pasta, and a handful of entrees) what’s on it is good. The pizza has a chewy wood-fired crust, and the silky cacio e pepe ricotta dumplings will have you waving a spoon in the air like a 2000s Yoplait commercial.

Though Obelix didn’t have much fanfare when it originally opened, this River North spot is now one of the most sought-after dinner reservations in town. On the surface, Obelix looks like a typical, white-tablecloth French restaurant. It’s not. It walks the tightrope of feeling formal without being stuffy. And that same balance is present in the food, which is filled with a mixture of classics like escargot and playful, fusion-y things like a foie gras taco.

photo credit: Derrick Koch

Logan Square

After a short closure, this excellent vegetable-centric "Midwestern pasta" spot reopened in a new, larger space. The menu isn’t that different, aside from a new section for things like lamb shank and salmon collars. But the bigger dining room (and the new chef’s table, and large bar) means that Daisies is packed by 6pm even on a random Wednesday. Make a reservation in advance, and eat pierogies while listening to an upbeat R&B soundtrack and the dull roar of other diners’ conversations.

Bronzeville Winery

Bronzeville

The fantastic funk and soul soundtrack, delicious food, and long wine list are just a few reasons to hang out at Bronzeville Winery for as long as possible. This American restaurant also has the perfect combination of loud music and conversational buzz that prevents the entire dining room from overhearing why your friend thinks health insurance is technically a form of gambling.

Suggested Reading

The Chicago Bar Hit List: Where To Drink Right Now

The best new bars in Chicago.

The Best Late-Night Restaurants In Chicago

Because night owls need to eat too.

The Hit List: New Chicago Restaurants To Try Right Now

We checked out these new restaurants—and loved them.

THE JOURNAL

Travel Inspiration

5 of the Coolest Places Visit in Chicago: Fora’s Guide

The Modern Travel Agency

https://www.foratravel.com/the-journal/places-visit-in-chicago

Wondering about the coolest places to visit in Chicago? We’re breaking down five of the city’s coolest sights and attractions, from the Art Institute of Chicago to the Magnificent Mile.

Want to visit Chicago in style? Connect with Fora to plan and book your trip with an expert travel advisor who can score you awesome perks at the best hotels in Chicago , offer A+ itinerary suggestions and help you anytime you need travel support.

The 5 best places to visit in Chicago

Read on for five of our favorite places to visit in Chicago. 

1. Art Institute of Chicago: one of the USA’s most prestigious art museums

Near the top of the list of things to do in Chicago : perusing the exhibits of the Art Institute of Chicago . This prestigious museum boasts one of the most comprehensive art collections in the world, with centuries of works spanning dozens of cultures both past and present. It’s a must-see for art enthusiasts and casual enjoyers alike. And if you’re interested in checking out more museums, there are plenty of great options nearby, such as the Chicago Cultural Center . 

Want more intel on the Art Institute of Chicago? Plan your trip with Fora .

2. Lincoln Park Zoo: an excellent place to visit in Chicago for families

Among Chicago’s coolest free places to check out, the Lincoln Park Zoo features over 200 different species of animals, from aardvarks from Sub-Saharan Africa to increasingly rare snow leopards from Central Asia. 

(Wondering what else to do in the city with kiddos? Our 4-day Chicago family itinerary has you covered.)

3. Millennium Park & Cloud Gate: a scenic oasis hosting some of Chicago’s most iconic sights

One of Chicago’s most famous attractions, Millennium Park — home to Cloud Gate, colloquially known as the “Bean” — is a well-manicured, urban green space sandwiched between Lake Michigan and Downtown. There’s a (huge) ice rink, tennis courts, botanical gardens, gorgeous fountains and even an adventure park for little ones. 

The park regularly hosts concerts at the Jay Pritzker Pavilion (a cool sight in and of itself), too. 

4. Garfield Park Conservatory: a lush and gorgeous botanical garden featuring thousands of rare species

Containing thousands of rare (and often threatened) plant species, the Conservatory at Garfield Park is easily one of the most impressive botanical gardens in the United States. Here, you’ll find a scenic mix of indoor and outdoor exhibits a few miles outside of Downtown Chicago, making for a lovely escape from the metropolis. 

Wondering where to stay in Chicago near Garfield Park? Connect with Fora for tailored recs.

5. The Magnificent Mile: the best place to visit in Chicago for upscale shopping & gastronomy

Image courtesy of InterContinental Chicago Magnificent Mile

If you’re looking for the best hotels in Chicago , luxe boutiques and an incredible variety of restaurants, the Magnificent Mile is for you. The stretch is also one of the best places to visit in Chicago to glimpse the city’s striking and varied architecture.

One of our favorite hotels on the strip is the InterContinental Chicago Magnificent Mile. Here, guests can enjoy exceptionally lavish amenities and expansive rooms, plus immediate access to the Magnificent Mile.

(Looking for hidden gems? See our local’s guide to Chicago .)

Fora Perks at InterContinental Chicago Magnificent Mile:

$100 hotel / resort credit.

VIP status.

Upgrade & guaranteed late check-out.

Need more ideas for places to visit in Chicago? Connect with Fora

Obviously, there are a lot more cool places to visit in Chicago than these five options. Want tailored suggestions (like a boozy Chicago craft beer adventure or a gastronomy tour) and access to awesome hotel perks like complimentary meals and upgraded rooms? Plan and book your trip with Fora .

Or if you’re not sure Chicago is the right setting for your next vacation, check out these guides for more travel inspiration:

5 of the Coolest Places to Visit in Colorado: Fora’s Full Guide

5 Awesome Places to Visit in Los Angeles

The Best Hotels in San Francisco: 5 Unique & Exciting Choices

The 4 Best Places to Visit in Arizona: Phoenix to Sedona

5 Luxe Hotels in Downtown NYC: From The Crosby to Arlo SoHo

Perfect Weekend Getaway on Lake Michigan

This article has been fact checked by Fora Advisor Elizabeth Coffey , an expert on travel to Chicago , Illinois.

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9 Unforgettable Family-Friendly Things to Do in Chicago

W hen seeking family fun in the Windy City, Chicago’s abundant attractions and vibrant culture offer an array of unforgettable experiences. From iconic parks to historic landmarks, the city invites families to embark on exciting adventures that cater to all ages. Discover the top family-friendly things to do in Chicago with your loved ones and create cherished memories that will last a lifetime.

1. Millennium Park: Modern Marvels and Outdoor Delights

A visit to Millennium Park promises a seamless blend of modern marvels and natural beauty, captivating visitors of all ages. Marvel at the enigmatic “Bean” sculpture that reflects the city’s skyline, explore cutting-edge modern art exhibits, and enjoy leisurely strolls in the family-friendly park. With an outdoor performance venue that hosts diverse events, Millennium Park provides an enchanting setting for creating lasting memories against the backdrop of Chicago’s skyline.

But that’s not all—Millennium Park’s Crown Fountain beckons families to cool off in summer as the interactive digital faces spout refreshing water, adding laughter to the air. Also, don’t miss the Jay Pritzker Pavilion, an architectural marvel hosting concerts and performances, where you can unwind while enjoying music and the city’s artistic spirit.

2. Engage in Sports Fever: Embrace Chicago’s Athletic Spirit

Immerse your family in Chicago’s passionate sports culture by attending live games featuring iconic teams like the Bears, Cubs, White Sox, Bulls, and Blackhawks. Be it football, baseball, basketball, ice hockey, or soccer with the Chicago Fire, the city’s fervor for sports is palpable. Experience the electric energy of the crowd and witness top-notch athleticism, giving your family a taste of the Windy City’s competitive spirit.

Additionally, the Chicago Sports Museum within Water Tower Place offers an interactive experience that lets you test your skills against Chicago legends, making sports history come alive. Explore memorabilia, engage in virtual games, and learn about the city’s sports legacy in an engaging and educational environment.

3. Stroll the Pedestrian Paradise: Downtown Delights

Downtown Chicago beckons families to explore its vibrant streets, where storefront attractions and pedestrian-friendly destinations invite leisurely walks. Along the scenic Lake Shore Drive, iconic stops like Navy Pier and the captivating Shedd Aquarium await. For shopping enthusiasts, the renowned Magnificent Mile on Michigan Avenue and State Street boasts a captivating blend of classic and contemporary shopping experiences, satisfying diverse tastes.

Moreover, Navy Pier’s Centennial Wheel takes family fun to new heights, offering sweeping views of Lake Michigan and the city skyline. Afterward, immerse yourselves in the interactive exhibits of the Chicago Children’s Museum , where creativity and learning converge for kids of all ages.

4. Immerse in Art and Entertainment: Theatrical Treats

Discover Chicago’s vibrant arts scene by treating your family to an array of performances and cultural explorations. From acclaimed Broadway shows like Wicked to ballet and orchestral concerts, the city’s theaters cater to all tastes. Delight in comedy at the famed Second City, where Saturday Night Live cast members launched their careers. Explore the city’s rich artistic landscape, including the captivating Lyric Opera.

Furthermore, Chicago’s Museum Campus features the Adler Planetarium, where families can embark on cosmic adventures through immersive shows and exhibits. Explore the mysteries of the universe and spark your family’s interest in science and space exploration.

5. Savor the Waterfront Experience: Navy Pier Adventures

Navy Pier, a historic freighter hub turned family-friendly attraction, promises a trove of adventures for visitors of all ages. Gaze in awe at the Ferris wheel towering 150 feet above, and indulge in onsite amusements like an 18-hole miniature golf course and musical carousel. Cultural gems like the Chicago Shakespeare Theatre provide captivating performances against the backdrop of Lake Michigan, creating a unique family experience.

For a touch of nostalgia, explore the Chicago Children’s Museum within Navy Pier, a haven for interactive learning and play. Engage your kids’ curiosity with exhibits that cover topics from art and science to engineering, all designed to make learning an exciting adventure.

6. Touch the Sky: Sears Tower Skydeck

Elevate your family adventure to new heights at the Sears Tower Skydeck, offering one of the most breathtaking views of Chicago’s skyline. Gaze out over up to 50 miles on clear days, marveling at the sprawling cityscape that extends to parts of Michigan, Indiana, and Wisconsin. Ascend together to the sky and share the awe-inspiring panorama from this iconic Chicago landmark.

As you stand on the Skydeck, don’t forget to step onto The Ledge—a glass balcony extending from the tower’s exterior. This exhilarating experience allows you to see the city beneath your feet, creating an unforgettable memory of conquering new heights together.

7. Dive into Marine Wonders: Shedd Aquarium Exploration

Shedd’s Aquarium right at the top of the best family-friendly things to do in Chicago . Embark on a captivating aquatic journey at the Shedd Aquarium, where marine life from around the world awaits discovery. While children marvel at the displays, adults find equal delight in the exotic species like piranhas, anacondas, and vibrant coral reefs. The aquarium offers an immersive experience that allows your family to explore the diverse ecosystems that thrive in our planet’s oceans and waterways.

For a deeper understanding of aquatic conservation, participate in Shedd’s educational programs that promote marine stewardship. Engage in interactive workshops, encounter marine animals up close, and leave with a renewed commitment to protecting our oceans.

8. Shop and Explore: The Magnificent Mile Experience

The renowned Magnificent Mile along Michigan Avenue is a shopper’s paradise, offering a mix of upscale department stores, luxury boutiques, and renowned hotels. Indulge in retail therapy at establishments like Gucci, Coach, Chanel, and Tiffany & Co., all while enjoying the charming cityscape. Explore this fashion-forward district and create lasting memories amidst Chicago’s retail wonderland.

To make your shopping experience even more memorable, consider visiting during the Magnificent Mile Lights Festival, where holiday lights illuminate the street, and festive activities like a tree-lighting parade and fireworks create a joyful family atmosphere.

9. Discover Cultural Gems: Chinatown’s Charms

Venture into the vibrant world of Chicago’s Chinatown, where a rich tapestry of shops, eateries, and cultural events awaits. Uncover the enchanting sights of parades, festivals, and unique celebrations that offer a glimpse into the heart of this cultural haven. From souvenirs to authentic cuisine, Chinatown invites your family to embrace its dynamic atmosphere and indulge in a world of sensory delights.

As you explore Chinatown, be sure to visit the Chinatown Square, where you’ll find a captivating fusion of traditional and modern architecture. Discover hidden gems like herbal shops, tea houses, and bakeries, offering an immersive experience that’s as educational as it is delightful.

Family Family-Friendly Things to Do in Chicago: Explore Chicago’s Treasures

As you explore family-friendly things to do in Chicago, you’ll unearth a treasure trove of experiences that cater to every age and interest. From modern wonders to historic landmarks, this dynamic city opens its arms to families seeking unforgettable adventures. Embrace the city’s diverse culture, rich history, and vibrant attractions as you embark on a journey of discovery, creating memories that will linger in your hearts for years to come.

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The 30 best restaurants in Chicago you have to try in 2024

There's no shortage of fantastic food in this city, but these Chicago restaurants make our list of top eats.

The best restaurants in Chicago come in all shapes and sizes, from pizza joints and Michelin-starred heavyweights to some of the best cheap eats Chicago has to offer. The cuisines are just as varied, with every corner of the globe represented through Korean, Mexican, Italian, Mediterranean and Japanese fare. Whether you're a lifelong resident or simply visiting for the weekend, stuffing your face at one of these restaurants is easily among the best things to do in Chicago . This belt-busting food scene shows no signs of slowing down, so we cut to the chase and ranked our essentials—the absolute best restaurants in town.

Our editors scour the city for great dishes, excellent value and insider info. We hope to provide an authentic snapshot of Chicago's ever-evolving dining experiences by updating this list constantly with the best new restaurants in the city as well as decades-old stalwarts that keep us coming back for more. It could be a mega-hyped destination restaurant or a remarkable hole in the wall: If it’s on the list, we think it’s terrific, and we bet you will, too. Many of the city's best chefs and restaurants are in Time Out Market Chicago as well, and you can scroll through the full vendor lineup at the bottom of this page.

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Time Out Market Chicago

• Restaurants

We've rounded up the best chefs in the city to join us at Time Out Market Chicago, a culinary and cultural destination in the heart of Fulton Market.

Best restaurants in Chicago

1.  Oriole

• Contemporary American
• price 4 of 4

What is it?  A two-Michelin-starred fine dining experience from chef-owner Noah Sandoval.

Why we love it: Chicago is home to a number of upscale tasting menus but few are able to match Oriole’s deft execution. Upon arrival, guests are escorted into a freight elevator and given a drink before the door opens to reveal the dining room. Though there’s no telling what Sandoval has in store each evening, you can look forward to a minimalist style of cooking that puts the spotlight squarely on the premium ingredients. Acclaimed mixologist Julia Momose and beverage director  Emily Rosenfeld complement the food with inventive cocktails and an Old World-inspired wine list.

2.  Kyōten

• Logan Square

What is it?  An eight-seat sushi counter run by bold and ambitious chef Otto Phan.

Why we love it: Phan left Austin, Texas to come to Chicago with the goal of creating the city’s best sushi. He fulfills those aspirations every night at his nondescript Logan Square restaurant, which is also one of the most expensive experiences in town. Those who are able to secure a seat are treated to a front-row view of the chef slicing raw fish and serving it on extra large rice grains that have been seasoned with aged red vinegar. You’ll pay a pretty penny but Kyoten’s omakase provides some of the finest bites money can buy, made with luxurious products flown in from Japan.

3.  Birrieria Zaragoza

• Archer Heights
• price 1 of 4

What is it? A family-owned Mexican spot in Archer Heights that's the G.O.A.T. when it comes to goat meat.

Why we love it : Thick handmade tortillas, salsas made to order, bright-pink agua fresca—you can get all of that to go. Their only purpose, however, is to accompany the restaurant’s signature platters of chopped goat meat. Unlike other birrierias, this goat doesn’t touch a consommé until it’s plated, when some of the tomato-based broth is spooned over it. At that point, a good dousing of hot sauce, and maybe a squeeze of lime and some onions, is all you need for the city’s best tacos.

4.  Johnnie's Beef

What is it?  An old-school Italian beef and ice stand over in Elmwood Park.

Why we love it: Just like with deep dish pizza and Chicago-style hot dogs, locals will never agree on the best Italian beef maker. The closest to a consensus is Johnnie’s, a legendary spot that necessitates a pilgrimage to the suburbs. You’ll have plenty of time to decide on what to order as you wait in line behind regulars, but we suggest getting the beef—dipped and with hot peppers. Order a lemon Italian ice to cool your mouth off afterwards.

5.  Monteverde

• price 3 of 4

What is it? Top Chef alum Sarah Grueneberg's pasta playground in the West Loop.

Why we love it: Italian food is meant to be shared, and at Monteverde, that's never an issue. Fill your table with a smogasboard of small plates, handmade pastas and shareable mains (read: they're freakin' huge). You absolutely mustn't skip the burrata e ham starter—which comes with warm English muffin-like rounds called tigelle—nor the spaghetti al pomodoro, a simple but soul-affirming dish that stars Grueneberg's spot-on roasted tomato sauce.

6.  Kasama

• East Village
• price 2 of 4

What is it? A modern Filipino-American bakery and fine dining restaurant from husband-and-wife team Tim Flores and Genie Kwon (Oriole), Kasama boasts both a Michelin-starred tasting menu and a selection of casual daytime dishes that'll have you saying “I'll take one of each.”

Why we love it : Believe any and all of the hype on this one: Kasama really is as good as they say it is. Come by in the morning for brunch fare like a longanisa-topped breakfast sandwich or a full Filipino breakfast (longanisa/tocino, fried egg, garlic fried rice and pickled papaya) and some of Chicago's best pastries. At night, book a coveted seating for the restaurant's 13-course tasting menu, a Filipino-inspired journey that swings from dishes like nilaga with A5 wagyu to a perfect little croissant served with a sprinkling of freshly shaved black truffles.

Time Out tip: If you don't have your heart set on dining indoors, skip the inevitable weekend line and order online for pickup—we promise your meal will taste just as good. 

7.  Virtue

• Soul and southern American

What is it? Chef Erick Williams's love letter to the Southern experience of cooking through passed-down recipes and reimagined expressions.

Why we love it : You can practically feel the soul oozing from the menu at this Hyde Park restaurant. It's because Williams cooks with his heart, whether he's plating fried green tomatoes with tender shrimp and creamy rémoulade or he's fixing his famous collards, which arrive studded with hunks of smoked turkey meat. Second only to the food is the ambiance, which is sexy without trying too hard—perfect for a cozy date night.

8.  Vito and Nick’s Pizzeria

What is it? The king of thin-crust pizza done Chicago-style.

Why we love it: Serving pies since 1949 (although this location opened in ’65), Vito and Nick’s is a Chicago tradition. The cracker-thin, tavern-style crust is loaded up with rich red sauce, gooey mozzarella and fennel-flecked sausage chunks; test the limits with a few more toppings—we like mushroom, pepper, onion and black olives on ours. For the complete experience, stop by to sip an ice-cold Old Style in the dining room while catching a glimpse of the Bears or Sox game on TV.

9.  Smyth + The Loyalist

• American creative

What is it? John Shields and Karen Urie Shields’s two-for-one special in the West Loop: a fine-dining destination upstairs and the city's best burger in the sultry basement.

Why we love it : You can choose your own adventure at this double feature—and neither option will lead you astray. Cozy up on the couch with the Loyalist's famed Dirty Burger, a messy medley of cheesy, oniony goodness that's now available for takeout and delivery. Or splurge for Smyth's multi-course tasting menus, a three Michelin-starred exploration of Smyth County, Virginia. 

10.  Daisies

What is it?  The noodle palace from Joe Frillman that recently moved into a new, larger home in Logan Square.

Why we love it : There's something about tucking into a bowl of handmade pasta that feels like a big, warm hug. That's why we ring Daisies when we've had a long day. The menu is built around a roster of rotating pasta dishes that change with the season to highlight super-fresh ingredients like lentils, stinging nettle and green garlic. Each bite tastes a bit more special when you hear about Frillman Farms, which is owned and operated by Frillman's younger brother, Tim, and provides produce to the kitchen (as well as many other top eateries across the country). The new space is also now open durinig the day, offering coffee and delightful pastries from Leigh Omilinsky.

11.  Red Hot Ranch

What is it? A no-fuss, late-night siren song that slings some of the tastiest burgers in town.

Why we love it : What Chicagoan hasn't found themselves at Red Hot Ranch in the wee hours of the morning in search of sustenance? For less than $7, one of the city's best cheeseburgers is yours—with thick-cut fries to boot! Thin, griddled patties shine with a little help from melty cheddar, LTO and special sauce. It's simple but undeniably decadent. Still hungry? Toss in a half-order of fried shrimp, which arrive golden in hue and accompanied by cocktail sauce for dipping. Then, sit back and let the food coma commence.

12.  Mi Tocaya Antojería

What is it? Translating to "my namesake" in Spanish, Mi Tocaya is a term of endearment that chef Diana Dávila has bestowed upon her neighborhood Mexican restaurant in Logan Square.

Why we love it : Dávila recreates childhood memories through her food, offering guests a lineup of soul-warming dishes like a carne asada burrito and fish in mole blanco. The guac, which is dusted with chile ash, is still on the menu, and a slate of cocktails rounds out the mix (the negroni is a unique twist on the classic).

13.  Jeong

• River West/West Town

What is it?  An upscale Korean restaurant from talented chef Dave Park and his partner Jennifer Tran.

Why we love it: Jeong is the fanciest Korean experience in Chicago, bar none. Park, who previously ran celebrated food court stall Hanbun in the suburbs, uses modern preparations to elevate traditional flavors. His tasting menu showcases gorgeous and inventive plates, like a disc of salmon tartare topped with doenjang yuzu gastrique, crunchy rice pearls and dollops of crème fraiche.

14.  Lem’s Bar-B-Q

• Greater Grand Crossing

What is it? A rite of passage for local and visiting chowhounds alike, Lem's is an institution-status barbecue house that deals in meaty things and fried chicken.

Why we love it : Chicago may not be known as a barbecue destination in its own right, but Lem's single-handedly puts the South Side on the map with its unique aquarium-style smoker, which weighs in at 64 square feet. Regulars love the rib tips and hot links—and luckily, the combo meal gets you a taste of both. It's takeout only at Lem's, so plan on dining in your car or taking this saucy feast home.

15.  Manny’s Cafeteria and Delicatessen

What is it?  Chicago's answer to Katz's Delicatessen, where cooks in paper hats serve gigantic sandwiches, bowls of matzo ball soup and cafeteria classics like meatloaf and pepper steak.

Why we love it: Whether you're showing up for breakfast, lunch of dinner, the Jewish deli fare at Manny's is gonna fill you up. Bring an appetite and order a generous bagel and lox, the signature corned beef or simply ask the folks behind the counter what's good today.

Time Out tip: Love Manny's meats, cheeses and bagels? You can order them in bulk and stock your home deli with everything you need to make the perfect bagel and lox.

16.  Boka

• Lincoln Park

What is it? The fine-dining beacon that started Boka Restaurant Group, one of Chicago's finest culinary collectives.

Why we love it : In its 20-plus years on Halsted Street, Boka has racked up a trophy case worth of awards, including one long-standing Michelin star and a handful of Jean Banchet Awards. But we prefer to let chef-partner Lee Wolen’s impeccable techniques—on everything from dry-aged duck and roasted chicken to ricotta gnudi—do the talking. It'd be a shame to skip dessert from pastry chef Kim Mok, who whips up dreamy, sugar-filled confections with serious range—from chocolate pavlova to mochi brownie.

17.  Bavette’s

• River North

What is it?  A sultry, vaguely French-inspired steakhouse from Hogsalt Hospitality.

Why we love it:  In a city inundated with chophouses, Brendan Sodikoff manages to keep things fresh and exciting. Even if you're not a huge fan of beef (which is top notch, BTW), the menu offers fantastic alternatives like divine fried chicken and shortrib stroganoff. A slice of chocolate cream pie provides the perfect ending to one of the most romantic and chic experiences in Chicago.

18.  Lula Cafe

What is it? A unanimously beloved neighborhood darling that's been doing the whole farm-to-table thing long before it was a thing .

Why we love it : There’s a reason Lula has been a Chicago staple for more than two decades. Chef-owner Jason Hammel and his team present dishes made with the freshest seasonal ingredients, and it shows—from pastries to turkey sandwiches to roast chicken, e verything you'll eat here tastes like it's been thoroughly iterated and perfected.

Time Out tip:  Lula serves brunch every day, so if you're free on a Thursday or Friday morning, your Classic Lula Breakfast Burrito awaits.

19.  La Chaparrita

• South Lawndale

What is it?  A taqueria attached to a corner store.

Why we love it: Focusing on tacos de fritangas, a specialty of Mexico City, La Chaparrita offers tortillas filled with a variety of muscles and organs that have been fried in a circular metal pan. The must-try is the crispy tripe taco, and don’t forget to wash it down with a cup of cold horchata.

20.  Maxwells Trading

What is it? A vaguely “contemporary American” restaurant from acclaimed chef Erling Wu-Bower.

Why we love it: The menu draws on all sorts of influences, making it tough to categorize the cuisine at Maxwells Trading. What’s easy to understand, though, is why we’re smitten with it—suzuki tartare announces its arrival with intoxicating aromas; brûléed sweet potato bathes in a northern Thai-style curry; and a steak salad is delicious in its simplicity. You may have to plan ahead to snag a table, but it’s well worth the effort.

21.  Qing Xiang Yuan Dumplings

• Armour Square

What is it?  Known to many as QXY, this Chinatown mainstay is the dumpling authority of Chicago.

Why we love it: When it comes to dumplings, we're of the mindset that more is always better. It's why we flock to QXY for the seemingly endless menu that details dozens of fillings that are sorted by protein—from pork and pickled cabbage to scallop and lotus root. If you can dream it, they probably have it. Place your order with the whole household in mind—that way, you can try a few different flavors in one sitting.

22.  El Che Steakhouse & Bar

What is it?: An Argentinian-influenced steakhouse that pays homage to the country’s beloved asados.

Why we love it: The smells coming from the kitchen’s 12-foot custom-built hearth are intoxicating and serve as a love letter to Argentina. Chef John Manion’s selection of flame-kissed veggies, meats and seafood are unrivaled, boasting premium cuts from sources like Creekstone Farms in Kansas and Michigan’s Vander Farmers. For an authentic South American experience, try the parrillada platter. It’s loaded with sweetbreads, morcilla, chorizo, steak, bone marrow and much more.

Time Out tip: If you want to get up close to the fiery action, book a seat at the chef’s counter. Manion also offers grilling classes.

23.  Galit

• Sheffield & DePaul

What is it? New Orleans chef Zachary Engel's (Shaya) raved-about—and Michelin-starred—entry to Chicago's dining scene: a Middle Eastern eatery in the heart of Lincoln Park.

Why we love it : When we heard that Engel was packing up his bags and moving to Chicago, the anticipation was palpable. And so far, the James Beard Award winner hasn't let us down. Instead of an a la carte menu, guests choose their own four-course adventure. The kitchen orchestrates a parade of hummus, fire-roasted veggies and proteins, balloon-shaped pita and addictive sides. 

24.  HaiSous Vietnamese Kitchen

• Lower West Side

What is it? Chef Thai Dang and co-owner Danielle Dang's love letter to Vietnamese cooking, showcasing rich flavors and overlooked dishes.

Why we love it: No matter how familiar you may be with Vietnamese cuisine, there's a good chance that something on HaiSous's menu will surprise you. Stick to standards like crispy wings covered in caramelized fish sauce or branch out by trying an octopus salad with eggplant confit. If you prefer a guided dining experience, order one of the tasting menus served family-style.

25.  Akahoshi Ramen

What is it? A dream realized for home-cook-turned-chef Mike Satinover.

Why we love it: After years of doing pop-ups, Satinover (best known as ramen_lord on Reddit) took the plunge and opened his own noodle shop in Logan Square. Armed with knowledge and experience gained from time spent studying abroad in Japan, he presents a tight menu of ramen and sides. We slurped the namesake Akahoshi Miso ramen—a soulful bowl of rich broth teeming with homemade Sapporo-style noodles, bean sprouts, green onions, bamboo shoots and chashu—until there was nothing left, but Satinover’s monthly specials (spicy miso on our visit) deserve a spot at your table, too.

Time Out tip: The restaurant accepts walk-ins each night starting at 5pm. But if you don’t feel like waiting an hour (or more), reservations go live at noon on Mondays.

26.  Tempesta Market

What is it? A deli and sandwich shop from a father-son duo.

Why we love it: The menu rotates constantly, so your go-to sandwich may be here today and gone tomorrow, but that just means there’s always an opportunity to discover a new favorite. One offering that never leaves the lineup is the Dante, a riff on the Italian sub that’s loaded with six layers of house-cured meats.

Time Out tip: Get some ‘nduja to take home. The spicy, spreadable salami from Italy’s Calabria region is the signature specialty.

27.  Taqueria Chingón

What is it? A tasty homage to the streetside eateries of Mexico City, Taqueria Chingón brings pozole, ceviche and tortilla-wrapped meats to Bucktown.

Why we love it: The tacos al pastor are a must, with tender bits of pork finding their match in creamy avocado salsa, sweet pineapple and flecks of cilantro. Vegetarians aren't left out of the fun: There's a veg-based version of the dish that subs in portobello mushrooms and celery root to create a spot-on rendition that's anything but boring. And if you're feeling extra hungry, the churros are an irresisitible dessert.

28.  Mott St.

What is it?  An Asian fusion spot that serves an eclectic selection of street-food-inspired bites.

Why we love it: The core of the menu is Korean, but influences from other Asian cuisines are littered throughout. You’ll sit down to options such as jumbo everything wings, pork-shoulder-stuffed cabbage and udon noodles with marinated cod roe and kimchi. The ballyhooed Mott Burger is also as good as advertised—an East-meets-West creation packing double patties, sweet potato shoestrings, miso butter onions, American cheese, dill pickles, pickled jalapenos and hoisin aioli.

Time Out tip: If you want to eat the burger at a table, it’s only offered in the dining room before 7pm. Otherwise, it’s available all night long at the bar.

29.  Tanta

What is it?  A Peruvian standout sporting a fabulous rooftop during the summer months.

Why we love it:  Tanta celebrates the cooking of South America with a menu that touches on all of the greatest hits. There are ceviches and tiraditos aplenty, in addition to Nikkei bites, which are a fusion of Peruvian and Japanese flavors. But you also can't go wrong with the heartier items like the pollo a la brasa and the chaufa aeropuerto—fried rice studded with char siu pork and veggies.

30.  Perilla

What is it? A modern Korean barbecue restaurant.

Why we love it: Most of Chicago’s beloved Korean barbecue joints are no-frills, mom-and-pop operations. But Perilla bucks that trend and feels like it was imported straight from L.A. While the meats are the star of the show (the L.A.-style galbi and marinated A5 wagyu never disappoint), don’t overlook other standouts like the silken tofu stew and Korean fried chicken wings.

Local chefs, restaurants and concepts we love so much that we welcomed them into Time Out Market

Restaurateur Louie Alexakis knows a thing or two about Greek cuisine, having spent nearly three decades working in the restaurant biz in Greektown and nearby suburbs. He and partner Lou Canellis drew from that experience to open Avli Taverna—a concept that puts a contemporary spin on regional Greek dishes—in Lincoln Park in 2018. Four years and multiple Chicago locations later, Alexakis has brought a highlight reel of dishes to Time Out Market, with a menu broken into three categories that capture the full spectrum of Avli’s approach to Greek cuisine. Whether you’re in the mood for flaky spinach pie, filo-wrapped prawns or chicken souvlaki served on house-made pita bread, Avli delivers an authentic taste of Greece and its diverse food culture.

When co-owners Manish and Rina Mallick first traveled to Goa, they were captivated by the region’s beautiful white sand beaches and Portuguese architecture. But the coastal Indian state’s delicious cuisine left an even bigger impression, with pristine seafood served alongside spicy curry and fluffy poi bread. The pair founded Bar Goa to share these delicacies with Chicagoans, serving a variety of dishes that just happen to pair nicely with a cold beer or a refreshing cocktail.

Bill Kim Ramen Bar

Steaming bowls of noodles have been a fixture of chef Bill Kim’s menus ever since he opened his first restaurant, and diners have always been eager to slurp his latest creations. Originally launched as a delivery-only concept, Bill Kim Ramen Bar specializes in broths that draw on Korean, Vietnamese and Mexican flavors, garnished with a creative array of toppings. Whether you’re looking for a conventional bowl or ramen or something a bit more adventurous, Kim has something you can enjoy by the spoonful. 

Every morning deserves the perfect start, and that’s precisely what you’ll get at Chitiva Cafe. Backed by award-winning pastry chef Steven Krizman, the extensive all-day menu features an assortment of baked goods, from fresh fruit Danishes to buttery croissants, alongside breakfast sandwiches, caffeinated beverages and more. For those with a sweet tooth, indulgent desserts like the chocolate marquise provide an impeccable ending to any meal. And don’t think twice about grabbing a delightful treat to savor later when the craving calls.

When Bonni Cameron took over County BBQ in 2020, she recognized the importance of preserving a winning formula. For more than a decade, the Little Italy restaurant has been serving up a diverse array of smoked meats, inspired by traditions from all across the country. Here, you can savor melt-in-your-mouth Texas-style brisket, succulent Carolina pulled pork and finger-licking rib tips prepared the Chicago way—each perfectly complemented by three house-made sauces. Of course, no barbecue feast would be complete without the essential sides so don’t forget the mac and cheese—crafted with beer cheese sauce—and creamy corn pudding.

Growing up in Tigray, Ethiopia with 10 other siblings, chef Tigist Reda learned at a young age how to cook for large groups. Her passion for entertaining turned professional in 2007 when she opened Demera to showcase the bold and vibrant flavors of her home country. Prepare to get hands-on as you scoop up dishes like doro wot—spicy and fragrant chicken stew—with the spongy sour flatbread known as injera. It’s the perfect communal dining experience, but we won’t blame you for not wanting to share.

Drawing inspiration from the modest origins of the hamburger, chef Jorge Kauam’s German-American concept offers a variety of smashed creations that blend the comfort of familiarity with striking inventiveness. Through modern techniques and premium ingredients, including a specially crafted spice rub for the beef patties, Kauam presents umami-rich options like the namesake Gutenburg Burger and the indulgent Guten Belly Burger, which comes adorned with luscious caramelized pork belly. And don’t overlook the accompaniments—the sweet potato fries elevated with brown butter and blue cheese are an essential complement to every order.

JoJo’s ShakeBAR

The classic diner gets a dose of ‘80s- and ‘90s-inspired nostalgia at JoJo’s Shake Bar, where visitors can sip decadent milkshakes beneath photos of Biggie Smalls, Bill Murray and other heroes from the era. You can opt for a customized flavor or try a milk bar (essentially a milkshake in popsicle form), but we also suggest one of the shop’s signature Biggie Shakes if you’re feeling adventurous: Topped with a cornucopia of cookies, candy and marshmallows, they’re a delightful sugar rush and a blast from the past all at once. 

Chef Rodolfo Cuadros refers to himself as a “nomad” after a decade spent working alongside Latin American cooks in Miami, London and France. When he opened Wicker Park restaurant Amaru in 2019, Cuadros set out to serve pan-Latin cuisine and share parts of the various cultures that inspire his recipes. Lil Amaru is a continuation of Cuadro’s mission to explore the soul of Latin American cooking, focusing on delicious dishes that are commonly sold by street vendors in countries like Mexico, Cuba and Colombia.

Lizzy J Cafe

Paying tribute to the influential women in her family who ignited her passion for cooking, Jamie Gilmore delivers Southern-style brunch fare infused with Creole love. At Lizzy J Cafe, the menu boasts all-day specialties like a crab cake Benedict, lemon ricotta pancakes and roasted lamb chops served alongside eggs and breakfast potatoes, complemented by a selection of refreshing teas and lemonades. No matter the hour, come in for a leisurely sit-down experience that satisfies with an array of comforting dishes.

A seasoned veteran of the sushi world, Ismael Lucero Lopez has spent decades meticulously refining his skills in slicing pristine fish. At  Madai , the menu honors traditional Japanese flavors while weaving in elements of Latin and Pan-Asian influences. Satisfy your seafood craving by indulging in inventive maki rolls like the El Baja—panko ebi, tuna and avocado, crowned with marinated jalapeños—or a selection of nigiri, sashimi and chirashi bowls. Whichever you choose, you’ll savor the essence of fresh, open waters through Lopez’s impeccable creations.

Sporty Bird

Art Smith has donned many hats during his illustrious career, from chef to diplomat to sports team owner, but one thing that’s been consistent is his unwavering passion for Southern hospitality. At Sporty Bird, you can get your hands on Smith’s famous fried chicken, which has been a longtime favorite among locals and luminaries alike. Accompanied by decadent mac and cheese, it’s everything you’d expect from a celebrated, two-time James Beard Award winner. If you’re in the mood for a handheld, the array of inventive chicken sandwiches promise to satisfy. And lest we forget, save room for dessert—the hummingbird cake is an irresistible delight that simply can’t be missed.

• Wicker Park

Chef Bill Kim keeps our bellies happy with his playful menu of Asian staples at this sunshine-filled restaurant in Wicker Park. Start with an assortment of dumplings, which are available by the piece in flavors like pork and cilantro and chicken red curry. You'll want to save room for hearty entrees like ramen with braised pork belly, creamy coconut curry pho, fried rice bowls and Thai fried chicken. The youngsters won't feel left out: The kids' menu offers fan-favorites like belly-warming noodle soup and PB&J soft serve.

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10 Ridiculously Fun Restaurants in Chicago

800 W Randolph St Chicago, IL 60607

(312) 929-4580

• http://auchevaldiner.com/chicago/pickup-delivery/

1462 E 53rd St Chicago 60615

(773) 947-8831

• https://www.virtuerestaurant.com/

2537 N Kedzie Blvd Chicago 60647

(773) 489-9554

• http://lulacafe.com/

1927 W. North Ave. Chicago, IL 60622

(773) 772-4422

• https://www.piecechicago.com/

1758 W 18th St Chicago, IL 60608

• (312) 285-2710
• https://5rabanitosdotcom.wordpress.com/5-rabanitos-menu/

3505 N Clark St, Chicago, IL 60657

(833) 466-3758

• https://www.deucesmlb.com

• 180 N Upper Wacker Dr, Chicago, IL 60606
•  (312) 526-3345
• https://www.beatnikontheriver.com/

1112 N State St, Chicago, IL 60610

(312) 586-2150

• https://www.viceroyhotelsandresorts.com/chicago/somerset

• 435 N Clark St, Chicago, IL 60654
•  (312) 610-4220
• https://www.threedotschicago.com/

353 W Hubbard St, Chicago, IL 60654

(312) 464-0500

• https://www.thehamptonsocial.com/chicago-river-north

Whether you are on vacation and visiting the city or a Chicago native, one of the crucial aspects you need to know is the eateries in the town. Chicago is one of the cities many people get to explore and enjoy its beauty, and this fun does not exclude trying out new cuisines. There are many eateries for you, but today we focus on the top 10 most fun restaurants in Chicago where you can enjoy your meals and have good times.

Picture a sports bar on steroids, and then you almost have Deuce’s. This spot is decked out floor to ceiling in sports gear, mainly Cubs of course, but they also have string lights and tons of other funky decorations going on in here. There’s also a great outdoor patio that just screams “day drinking!” Whether you’re going to watch the ball game or just to get some drinks, this place has the best atmosphere for casual dining. 

Start the afternoon off with some of their delicious cocktails like the Sidecar or the Cooperstown cocktail. For the table, great food options abound! Split the giant pretzel, major nachos, or some loaded tots. If you’re interested in a meal, try the MLB sliders or the meat lovers flatbread. If you like to have fun in a sporty environment, this is the spot any day of the week.  

2. Beatnik On The River

180 N Upper Wacker Dr, Chicago, IL 60606 

(312) 526-3345

For some of the best Mediterranean food and one of the prettiest restaurants in Chicago, Beatnik On The River is a place you need to check out. You’ll definitely want to make a reservation because this place gets quite busy, and you’ll understand why once you see what’s going on here. The inside looks like a palace with gorgeous decorations filling the entire restaurant. Beatnik is right on the river so there are endless views, both inside and out. 

As for the food, there are tons of delicious options, and you can’t go wrong with any of them. Start off with one of the spreads like the smoked octopus and hummus or the pistachio tzatziki. For the main course, go for something classic like the steak kabobs or something a little less classic like their double cheeseburger, which is also delicious.

3. Somerset

Somerset is located in the beautiful Viceroy Hotel, which means it is in a great location and is dare I say, trendy? The color scheme is gold and blue giving the spot a very 1920’s vibe. It is picturesque beyond belief, inviting, and they have some incredible menu options. They serve brunch, lunch, and dinner so you can enjoy this great spot any time of the day. 

If you are just stopping in for some bites and drinks, try the local burrata mozzarella or the wagyu steak tartare. For dinner you have options from fish, meat, pasta and more. From the mouth watering roasted beef short rib to miso-citrus salmon, you will find something to love on this menu. Try some cocktails like the Sinatra or the Monroe, or go for a nice glass of wine. You will leave this place feeling like a movie star from the 20’s. 

4. Three Dots and a Dash

435 N Clark St, Chicago, IL 60654 

(312) 610-4220

With great music, awesome decorations, hand crafted cocktails, and so much more, Three Dots and a Dash is Chicago’s hottest tiki bar. The experience you’ll get here is unlike any other. The dimmed lights inside add to the incredible ambiance here. 

If you’re in the mood for something to eat, the pu pu platter is sure to satisfy you. Want something a little smaller? Try the Thai fried chicken or the coconut shrimp! The main course here: the cocktails. They are as delicious as they are pretty. There are endless options to choose from and the menu breaks it down by drink. Classic cocktails, modern cocktails, mai tais, group drinks, literally anything you can imagine. Even when it’s freezing in Chicago, this tiki bar will make you feel like you’re in a summer oasis! 

5. Hampton Social 

Although Hampton Social has a few locations around the country, it is always an experience every time you go to one. Known for its adorable neon lights and unique decorations, this is a spot to check out no matter the city! They have an awesome outside patio, and tons of comfortable seating inside on those chillier days. The interior has serious beach vibes, and you can’t leave here without getting a picture under the “rosé all day” sign. 

Hampton Social serves brunch and dinner and has an awesome happy hour. For brunch choose from items like shrimp tacos, steak and eggs, the sunrise beach bowl, and so many other delicious options. If you join for dinner, there are so many more wonderful options from the cold bar, pizza, handhelds, large plates and more. You have to try some of their specialty cocktails before you go like the Honeycove and Hampton Vibes. 

6. Au Cheval

Wondering where you can take your friends who have never been to the town for lunch? Worry not, the Au Cheval has you sorted. With various meals ranging from gluten-free meals to takeaways and cocktails, this is the place to be. As Chicago is famous for meat and all associated with it, the Cheval burger is an irresistible kind in Chicago. With the precision used in making it, their food quality makes it second to none. As an accompaniment, the luscious side of fries or deep-fried potatoes will fill you to the brim. Additionally, the place is suitable for good brunch to dinner meals ranging from fried bologna sandwiches to pork porterhouse.

An upside to this joint is the flexibility in running hours; therefore, even after leaving the club, you can be able to grab yourself a good meal before calling it a night.

Whenever you are in the mood of trying out new and unique styles of cooking, this is the place to be. Virtue is well-known for the fantastic Southern Cuisines with various meals like pork chops in barbecue and seafood. The quality of the shrimps and other kinds of seafood made will make you come back for more. The restaurant also has cocktails, which are made based on your preference. The drink of choice’s versatility will complete that night out you had in store for your friends. This is undoubtedly a joint you should try out.

Moreover, the restaurant’s calm and peaceful ambiance makes you enjoy the culinary, accompanied by exemplary customer satisfaction. It is essential to make an early booking as it can fill up quickly. Making an early reservation for your friends will undoubtedly be the perfect decision.

8. Lula café

Chicago is the steak home; if you are a meat lover, this is the place to be. Lula café is celebrated due to the excellent quality Italian steak. Being one of the signature foods in the restaurant, its preparation is very top-notch. The restaurant also has one of the best contemporary pasta that can be a good accompaniment for your fish or steak. The originality in the cuisines makes the restaurant among the top picks for anyone looking for an excellent savory meal enriched in good flavors. Nonetheless, they have accommodated all the vegans as the menu contains different veggies and salads.

Additionally, the restaurant offers pre-orders delivered right at your home’s comfort if you don’t want to eat out. The varied menu allows you to choose from breakfast, brunch, and dinner.

9. Piece Brewery and Pizzeria

Nothing beats the joy of having a pint of beer and some good pizza with friends or colleagues. The Piece brewery and pizzeria is where you get to hang out with your friends while having good conversations. The diverse choice of pizza flavors allows you to enjoy rustic to contemporary pieces of pizza. This includes the red pizza and hot Doug’s atomic pizza. The restaurant is a haven as they also have different kinds of dips and toppings for you. Additionally, when you are having a good night out, the place is open till late, and you can also enjoy their happy hours.

The pizzeria ambiance is one of the best places to chat because of the large spaces where groups can be accommodated. Additionally, there are different activities you can partake in or watch while enjoying your pizza, making this a super fun restaurant! 

10. 5 Rabanitos

Whenever you want to enjoy Mexican delicacies, this is the ultimate plug. Rabanitos offer different Mexican cuisines such as tacos, which have various kinds of fillings you can choose from. These filings are versatile; hence they have a vegetarian type of tacos. This allows your vegan friends to enjoy them.

Additionally, they have queso fundido, accompanied by chorizo and poblanos with a side of tortillas. This tasty meal is enriched with melted cheese making you enjoy every bite. It is significant to note that the restaurant also offers gluten-free meals, which can be delivered right to your home.

11. Ed Debevic’s

The service at a restaurant can make or break your experience, and somehow at Ed Debevic’s, it does both…? For some kitschy fun, check out this retro 50s style diner. The servers are rude and sassy as part of their shtick. 

These most fun restaurants in Chicago have some of the best delicacies suitable for your whole vacation or exploration. We have taken a good analysis of their menus and observed the serenity, and we assure you that you will have the most memorable moments created in these unique food joints.

Editor’s Note: This article was originally published on January 26, 2021 and last updated on May 23, 2023 . Please refer to restaurant websites and social media pages for the most up-to-date information.  

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25 Things You Should Do Before Boarding a Plane, According to a Frequent Flier

We've rounded up 25 things you should do before your next flight so you can relax and know that you're totally prepared.

Between making sure your suitcase isn't an ounce over the weight limit and rushing to your gate before the doors close, air travel can be a stressful experience — but it doesn't have to be. We've rounded up 25 things you should do before your next flight, so you can relax and know that you're totally prepared.

1. Download and Use Your Airline’s App

Unless you're checking a bag, there's no reason to queue up at the check-in desk or deal with a fingerprint-smudged kiosk at the airport. Download your airline's app ahead of time, make sure your reservation details are in, and then use it to check in. That way, you can head straight to security when you arrive at the airport. Delta's app, for example, will even check you in automatically 24 hours in advance of your flight.

2. Get the Airline Credit Card

Don't fly enough to earn elite status? Airline credit cards offer cardholders perks similar to elites, including free checked bags and priority boarding. Carrying one of these cards can save you money on luggage and ensure you'll find carry-on space in the overhead bins ahead of the crowd.

3. Have a Status Strategy

Speaking of airline status, if you are going for gold (or silver, or platinum) this year, make sure your frequent-flier number is attached to all your airline reservations. Even if you're not flying your usual carriers, chances are the airline you're on is partners with another you fly more frequently thanks to alliances. That way, you can earn airline miles toward status on every single flight you take.

4. Check Aircraft Alternatives

Seats and amenities can vary dramatically, even from plane to plane within a single family of jets in a particular airline's fleet. Once you settle on an airline, double-check the aircraft type and seat map on the carrier's site to make sure you're flying the plane you want.

5. Assess Your Seating Situation

Whether you like a window or an aisle , it's worth checking SeatGuru 's detailed seat maps to confirm your chosen place on the plane won't be too close to the galley or the lavatories, with their associated noises (and smells!).

6. Stay Organized

Keep all your information in one place by using App in the Air or TripIt , two apps that do things like consolidate your flight statuses, check-in times, gate numbers, and nearby lounge locations, and will update you on schedule and gate changes.

7. Check Real-time Reports

Stay informed about your flight's status by using your airline's proprietary app. But you can also take it a step further by using FlightStats to track flight statuses, on-time performances, weather conditions, and even the flight history of your specific aircraft, all in real-time so that if your plane is delayed, you can be the first to know and the first to get rebooked.

8. Remember the Liquid Lowdown

Remember, any liquids you're carrying through TSA checkpoints must be less than 3.4 ounces (100 milliliters) and placed in a see-through bag no larger than a quart.

9. Sign Up for PreCheck, Already

Keep those shoes and belts on, leave the liquids and laptops in your bag, and forgo the full-body scans by getting TSA PreCheck . You could pay $70 for PreCheck itself or $100 for Global Entry , which also confers PreCheck (usually) and expedited immigration and customs access. Several credit cards, including the Capital One Venture and the Bank of America Premium Rewards card, will even refund you the application fee for either program.

10. Investigate Security Speed

Bypass the worst security checkpoints at over 200 airports around the globe by tapping into the MiFlight app's crowd-sourced, real-time checkpoint waiting times.

11. Size Up Your Bag

Many airlines have instituted strict size limits for carry-on bags, which are stringently enforced by eagle-eyed gate agents. Check your bag's dimensions at home and make sure they adhere to your airline's limits. Keep in mind that European carriers' limits vary slightly from those in the U.S. Blame it on standard versus metric.

12. Gather Your Gadgets

Phone: check. Laptop: check. Tablet: check. Camera: check. Spare charger: check. Power cords: check. Travelers are carrying more electronics than ever. Luckily, there are organizer cases galore to keep all your devices and cables within reach and ready for security screening.

13. Remove Those Batteries

Airlines instituted smart luggage battery bans in January 2018. If your bag has a battery pack, be prepared to show that it is removable in case your bag has to be gate-checked. But don't leave that battery pack at home, necessarily. Just because your airplane seat is supposed to have power ports does not guarantee that they'll actually work when you're on the plane.

14. Grab and Go

Hate airplane food, but afraid you'll miss boarding while waiting in a line at an airport restaurant? Use the Grab app to pre-order and pay for items at participating restaurants and vendors at airports in the U.S., Mexico, and across Europe. Place your order on your ride to the airport and pick it up on your way to the gate without breaking stride.

15. Connect for Less

Many airports offer free Wi-Fi , but beware of hackers. Using a VPN offers a measure of protection.

16. Lounge Around

Why wait at the gate when you can enjoy free Wi-Fi and snacks in the comfort of a lounge? LoungeBuddy posts reviews on airport lounges around the world, including their entry requirements and how you can score day passes. Several premium credit cards, including the Chase Sapphire Reserve and the Platinum Card from American Express, confer access to hundreds of Priority Pass lounges worldwide. Frequent travelers can also consider airline-specific cards such as the Delta SkyMiles Reserve, which gets you into its clubs.

17. Wear Comfortable Clothing

Airplane cabin climate settings seem to vacillate between icebox and toaster oven, with no habitable happy medium in between. And no one wants to touch those germy air nozzles, which only provide a hissing draft of dry air anyway. Dress for any contingency by wearing multiple light layers , and look stylish to boot.

18. Stick Your Neck Out

As airlines squeeze more and more seats into coach, ergonomics seem to be flying out the window. Luckily, travel pillow technology has never been better, with options for every type of sitter and sleeper. It's time to invest in a quality travel pillow that will spare your neck and back the worst effects of a long flight .

19. Bring Your Own Bottle

Avoid single-use plastic (and a bottle of water that costs $8 post-security) by bringing an empty travel water bottle with you instead. Some are even collapsible to save you space, and more airports have installed water bottle filling stations next to drinking fountains to make carrying your own that much more convenient.

20. Disinfect Everything

Due to the number of people passing through and touching everything, airports and airplanes are some of the germiest places around (though in the post-pandemic world, many airlines are taking additional steps to ensure your safety). Protect yourself as much as possible by using disinfecting wipes on your hands and your airplane seat once you get settled. Because they're not liquid, like hand sanitizer, wipes will also not count toward your carry-on liquid limit.

21. Moisturize Like Your Life Depends on It

Even on next-generation jets like the Boeing 787 Dreamliner and the Airbus A350, cabin humidity levels rarely top 20 percent (and are only around 8-10 percent on conventional aircraft). To avoid looking like a prune after your flight, pack a light moisturizer and apply it frequently.

22. Get a Jump on Jet Lag

Flying across multiple time zones? Use an app like Entrain or Timeshifter before you fly. Both help you gradually shift your pre-travel schedule toward your destination time zone based on your specific plans and preferences so that by the time you fly, you're already ahead of jet lag.

23. Park Like a Pro

Airport parking lots can fill up quickly during the busiest travel times. Use SpotHero to reserve a place in advance at lots near more than 40 airports throughout the U.S.

24. Understand Your Credit Card Protection

Flight delays and cancellations happen. If you travel frequently, it pays to carry a credit card you know will protect you under certain circumstances. Many offer compensation for delays, cancellations, lost luggage, and more if you use them to pay for travel plans. So, if you have to spend money staying somewhere overnight or replacing certain items, it won't come out of your bottom line. Before traveling, read your card's benefits packet carefully to understand what you're entitled to and how to go about claiming it.

25. Investigate Intelligent Insurance

Beyond delays, cancellations, and lost luggage, which are covered by most major credit cards, you might want to insure an expensive trip with a policy that includes provisions for emergency medical evacuation and cancellation for any reason. InsureMyTrip.com is a convenient resource for comparing travel insurance plans from major providers.

Bonus: Don't Forget the Essentials

If you're flying during the pandemic, you'll want to check your airline's guidelines for travel as well as your destination's requirements for incoming visitors. Stash extra face masks , wipes, hand sanitizer, and any other essentials in both your carry-on and checked luggage so you're never without them.

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