Chicago tours & attractions
Don’t leave without checking out these top sights..
Take a boat cruise through the heart of the city, see your reflection in “The Bean,” step outside one of the world’s tallest buildings. We’ve rounded up some of the city’s must-see sights, iconic attractions, and top tours to add to your itinerary. And don’t miss attraction passes for reduced admission to museums, activities, and beyond.
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Must-see Chicago attractions
Chicago Museum Campus
Shedd Aquarium
Chicago River
Millennium Park
Crown Fountain
DuSable Black History Museum and Education Center
Washington Park
Skydeck Chicago
Willis Tower
Museum Campus South
Museum of Science & Industry
Lake Michigan
360 CHICAGO
875 N. Michigan
Pullman National Historical Park
Historic Clock Tower
Lincoln Park Zoo
Lincoln Park
National Museum of Mexican Art
Garfield Park Conservatory
Garfield Park
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The 15 best chicago tours for 2024, according to reviews.
Foodies, architecture buffs and historians alike will appreciate these tours of the Windy City.
The 15 Best Chicago Tours for 2024
Alejandro Reyes | Choose Chicago
One of the best ways to sightsee your way through a new city is with the help of a local. With this in mind, U.S. News rounded up some of Chicago 's best guided tours. Whether you're sailing past Willis Tower on a river cruise or sampling some of Chicago's best deep-dish pizza on a foodie excursion, you'll gain a cultural and historical understanding of the Windy City during these tours.
Chicago Architecture Foundation River Cruise
Price: From $54 Duration: 1.5 hours
The Chicago Architecture Foundation's River Cruise ferries passengers along the Chicago River as docents from the Chicago Architecture Center regale them with the stories behind more than 50 notable buildings. The volunteer docents repeatedly win high praise from reviewers for their in-depth knowledge of the city's history and its structures. Many reviewers called this the best thing to do in Chicago. The cruising vessels, part of the Chicago's First Lady Cruises fleet, can carry up to 250 people and boast full-service bars and open-air upper decks.
For a different perspective of the city's iconic architecture, consider the twilight sailing, which costs a few dollars extra. For an additional $5, you can also gain admittance to the Chicago Architecture Center (which usually costs $14 on its own).
Check prices & availability on:
Chicago Food & City Tours – Gateway to the West Loop Food Tour
Price: Adults from $85; kids from $50 Duration: 3 hours
This foodie tour centers on the West Loop neighborhood's incredible dining scene, and provides insider insights to the area's evolution from a meat-packing and warehouse district to the Restaurant Row of today. Foods you may sample include doughnuts, hamburgers, pizza and cupcakes. Guides regularly earn five stars from travelers for their insight and enthusiasm. Reviewers find the tour worth the price for the generous amounts of food provided. What's more, group sizes are restricted to 16 people and tours do not involve extensive walking (a little more than half a mile).
Tours are offered Sunday, Tuesday and Thursday at 1 p.m. Hungry for more? The company also offers a tour inspired by the TV show "The Bear," which is set in Chicago, as well as a tour all about the city's most iconic foods.
Absolutely Chicago Segway Tours – Chicago Lakefront Museum Campus Tour
Price: From $65 Duration: 2 hours
The Chicago Lakefront/Museum Campus tour offered by Absolutely Chicago Segway Tours showcases many of the city's most popular attractions along its 5- to 6-mile route, including Millennium Park (the starting point), Grant Park , Monroe Harbor, the Field Museum , Shedd Aquarium , Soldier Field and the Adler Planetarium. Participants applaud tour guides for their expertise and professionalism and say this is a safe, fun way to see the city's top sights in a short amount of time.
Note that riders must be at least 12 years old to participate. Tours are available multiple times a day from spring through autumn. The company offers several other Segway tours, some centered around other parts of the city or with specific themes like architecture, crime and ghosts.
Inside Chicago Walking Tours – Dazzling Interiors of the Loop
Price: Adults from $30; kids from $25 Duration: 2 hours
Many travelers are familiar with Chicago's distinct architecture, but its equally captivating indoor spaces are not as well known. This tour reveals interior architectural details that visitors might otherwise miss. Guides take participants inside some of Chicago's most stunning buildings to admire elements like a gilded 80-foot-high ceiling, art deco lobbies, early Frank Lloyd Wright designs and rooms with stained-glass mosaics. Reviewers describe this tour, which involves about 1 1/2 miles of walking, as an informative and entertaining way to learn about the history of Chicago and its diverse, distinctive buildings. Others said this tour is great for first-time visitors and locals alike.
Tours operate Thursday through Monday at 11 a.m. Once you've toured all of the buildings at the street level, consider the company's Chicago Pedway tour, which tours the downtown underground tunnels that residents use to stay warm and dry during bad weather.
Courtesy of Bobby's Bike Hike Chicago
Bobby's Bike Hike Chicago – Bikes, Bites & Brews Chicago’s Signature Dishes Bike Tour
Price: From $85 Duration: 4 hours
This triple threat tour combines bicycling, food and beer. The 13-mile ride traverses the Gold Coast, Lakeview, Wrigleyville and Lincoln Park neighborhoods with stops for pizza, beer, cupcakes and hot dogs. Reviewers say the pace of the tour is easy and applaud the guides for their fun and engaging commentary. Others said they learned a lot about Chicago, calling the ride entertaining and educational.
Tours are generally offered daily at 11:30 a.m. and 5:30 p.m. (except during the winter). Note that the evening tour mostly bikes around downtown Chicago. If you're interested in venturing beyond downtown, book the morning tour. Tickets cover the cost of the bike rental as well as food and drinks. Participants must be at least 21 years old. If you're traveling with kids, try the company's Family & Food Bike Tour of Top Attractions.
Chicago Pizza Tours – Original Chicago Pizza Tour
Price: Adults from $75; kids from $45 Duration: 3.5 hours
Enjoy a crash course in what makes Chicago pizza so iconic on this delicious tour. You'll visit four independently run neighborhood pizzerias and sample six or more slices of pizza in a variety of styles (deep dish, tavern, artisanal and Neapolitan, to name a few). You'll meet downtown for your first slice before boarding a bus to neighborhoods like Lincoln Park, Lakeview and Bucktown. Reviewers compliment the informative and entertaining tour guides and insist that the tour is about more than just pizza, highlighting the various aspects of Chicago history, architecture and culture that's spotlighted during the nearly half-day excursion.
Tours run Saturday and Sunday at 11 a.m. The company also offers pizza crawls of downtown and Bucktown.
Chicago Gangsters and Ghosts Tour
Price: Adults from $35; kids from $17 Duration: 2 hours
If you're interested in the darker side of Chicago history, specifically its gangsters and ghosts, consider this walking tour. With a historian leading the way, you'll stroll for about 1.5 miles around the Loop – once known as the "Vice" district in the 1920s and '30s for its rampant partying, speakeasy saloons and underground tunnels used by bootleggers. Participants rave about the guides for their storytelling abilities and say the length of the tour is perfect for when you need a break from the city's more touristy activities.
Tours run four times daily beginning at 11 a.m. The company also runs a Gangster Food Tour that highlights some of the city's most iconic foods like deep-dish pizza and hot dogs, as well as the restaurants that once served as some of Al Capone's old hideouts.
Courtesy of Big Bus Chicago
Big Bus Chicago – The Big Loop - Red Route
Price: Adults from $49.50; kids from $35.10 Duration: 2 hours
Big Bus Chicago's hop-on, hop-off tours invite tourists to tailor their sightseeing excursions to their preferences by allowing them to spend as much time as they want at any of the 11 stops on the company's red route. Tour-takers can "hop off" a bus and explore any of the top attractions featured along the way, such as Skydeck Chicago , Navy Pier or Millennium Park, and then "hop on" a later bus. If you don't get off the bus, the entire route takes about two hours. Your ticket is valid for 24 hours, so you can hop on and off as much you please.
Buses run every 30 minutes starting at 10 a.m. daily and include prerecorded commentary in both English and Spanish. Reviews from recent travelers were mixed: Some riders loved the convenience of the bus, saying it puts you within easy walking distance of the city's best attractions, but others were disappointed with the quality of the prerecorded commentary and said you should try to seek out the few busses that feature a live guide. If you want to ensure you'll have a live guide on your bus, consider booking the nonstop, 90-minute Sunset Live Tour, which is offered from May to October.
Secret Food Tours: Chicago
Price: Adults from $79; kids from $69 Duration: 3.5 hours Follow a local foodie around the Loop district for what the company calls a "moving feast." You'll make six stops to sample some of the city's most notable dishes, including deep-dish pizza, gourmet popcorn, a Chicago-style hot dog, an Italian beef sandwich and a brownie (which was purportedly invented in Chicago). What's more, there's a secret dish revealed the day of the tour. Plus, tours are capped at 12 participants to ensure an intimate experience. Reviewers say guides do an excellent job of highlighting not only Chicago's distinct food scene, but also its history and architecture. They also advise that you'll want to come hungry as the portions are generous.
Tours operate daily at multiple times; the earliest tour departs at 11:30 a.m. The company can also arrange private tours.
Underground Donut Tour – Chicago: Downtown Tour
Price: Adults from $55; kids from $50 Duration: 2 hours Come hungry for this food tour, which visits four of the best doughnut shops in the city, including Doughnut Vault and Do-Rite Donuts. As you nosh on the sweet treats, your guide will share the history of each shop and the history of doughnuts in Chicago. Travelers recommend this tour for the knowledgeable, engaging guides and the delicious selection of doughnuts. They also say you'll learn about much more than doughnuts, as guides share historical tidbits about Chicago and recommendations for how to make the most of your trip.
Tours operate daily at 10 a.m.; additional 9 a.m. and noon tours are offered Wednesday through Sunday.
Graham Chapman | Choose Chicago
Urban Kayak Chicago Riverwalk – Historic Chicago Tour
Price: From $55 Duration: 2 hours
For a "duck's-eye," up-close view of the city, take Urban Kayak's Historic Chicago Tour. Starting at the Riverwalk , tour-takers paddle their kayaks on the main branch of the Chicago River with periodic stops at points of historical interest, where guides provide information regarding the city's famed architecture. Reviewers say this is a great experience, even for beginners, and recommend the tour for travelers looking for a unique alternative to the popular architecture river cruises. Meanwhile, others note that the experienced guides are skillful at navigating boat traffic.
Tours are offered multiple times a day spring through early fall. Urban Kayak also offers kayak rentals and paddleboarding classes.
Check prices & view availability on:
Shoreline Sightseeing – Skyline Lake Cruise
Price: Adults from $35; kids from $17 Duration: 45 minutes
If you've already taken an architecture cruise on the Chicago River and can't get enough of the views, consider this boat tour. Shoreline Sightseeing Skyline Lake Tours offer unrivaled views of Chicago's skyline, and many photo opportunities, via cruises along the Lake Michigan shoreline. The 6-mile trip provides views of notable landmarks, such as the John Hancock Center, the Willis Tower (aka the Sears Tower), Adler Planetarium and the Field Museum, as well as an informative prerecorded commentary. According to reviewers, these iconic buildings are much more visible from the water than they are on the street, though a few warned that it's difficult to hear the recorded commentary from certain areas of the boat (sit in the middle of the boat if you want to ensure you can hear the narration).
Travelers can purchase drinks at the onboard cash bar. Tours are offered daily spring through autumn (weather permitting) and depart from Navy Pier. Shoreline Sightseeing also offers architecture cruises along the Chicago River.
Ken Flisek | Courtesy of Tall Ship Windy
Tall Ship Windy – Chicago Skyline Sail
Price: Adults from $49; kids from $39 Duration: 75 minutes
Tall Ship Windy's Chicago Skyline Sail features views of the city from the deck of a 148-foot, four-masted schooner. Reviewers tout the remarkable views of the city's impressive buildings and, weather-permitting, the special experience of being able to actually sail and not rely on the boat's motor. What's more, tour participants commend the crew members for their professionalism, humor and knowledge of Chicago.
From spring through fall, there are generally four sails daily starting at 1 p.m.; the 1 p.m. sailing focuses on piracy in the Great Lakes and the Caribbean. Tall Ship Windy has a full bar on board (drinks are not included in the ticket price). In addition to daily sails, Tall Ship Windy offers evening cruises timed to the fireworks display at Navy Pier, which occurs on select dates in the summer.
Chicago Crime Tours and Experiences – Chicago Crime and Mob Bus Tour
Price: From $42 Duration: 2 hours
If you're a fan of true crime, you'll be intrigued by this bus tour, which explores the city's most famous gangsters and crime scenes. As you drive in a variety of Chicago neighborhoods, including the Gold Coast, Lincoln Park, the Loop, the Magnificent Mile , Old Town and River North, your guide will share stories and you'll watch historic video footage. The bus tour includes stops at the spots where gangsters like Hymie Weiss were killed as well as the site of the St. Valentine's Day Massacre. It also visits locales associated with Al Capone, Frank "the Enforcer" Nitti and Leopold and Loeb, among others. Reviewers laud the tours for providing a unique angle on Chicago's colorful history and describe guides as entertaining.
Tours are offered multiple times a day. For a longer tour with even more stops, consider the company's Night Crimes Tour.
Check prices & availability:
City Experiences – Chicago Seadog Lakefront Speedboat Tour
Price: Adults from $35; kids from $25 Duration: 30 minutes
Zip across Lake Michigan during this high-speed, narrated half-hour tour. During the ride, you'll see striking views of the Chicago skyline and hear some descriptions of the sights. Visitors praise the crew's knowledge and charisma. They also enjoy whipping along the waves. Keep in mind: The boat is open-air, which means you might get wet. The company also discourages pregnant women and travelers with back or neck sensitivities from participating.
Speedboat rides are offered daily spring through fall. City Cruises also operates a narrated architecture cruise, in addition to brunch and dinner cruises.
You may also be interested in:
- The Best Chicago Walking Tours
- The Best Chicago Segway Tours
- The Best Chicago Boat Tours
- The Best Hotels in Chicago
- The Top Romantic Getaways in Illinois
Tags: Chicago , Travel , food and drink , Vacations , Tours , Illinois Vacations , Midwest Vacations , US Vacations
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Home » Travel Guides » United States » Illinois (IL) » 15 Best Tours in Chicago (by a Local)
15 Best Tours in Chicago (by a Local)
The Windy City is the third largest city in the United States and comes with a variety of delights for any visitor. From food and craft beer to architecture and history, the Midwestern metropolis is packed with exciting experiences.
There are a variety of great tours run by locals across the city that help you dive deep into the things that matter most to Chicagoans. The unique history and culture of the city is best discovered with a local guide, and these tours will help you to dive deeper into what makes the city tick.
I’m a Chicago local and have been on many tours with friends and family visiting. To get you started here’s my list of the best tours in Chicago.
1. Chicago Skydeck + “The Ledge” Experience Ticket
The Willis Tower is the tallest Skyscraper in Chicago and this ticket allows you to go to the very top.
There are a bunch of exhibits on the way, to teach you about Chicago’s history and the deep cultural roots that connect the city. Once at the top, brave visitors can step into ‘the Ledge,’ a series of four glass balconies that give you views across Chicago as well as over the street below.
A theatrical presentation is also included in the ticket, which discusses the construction of the Willis Tower.
2. Chicago River Architecture Cruise
For a more relaxing tour experience, this river cruise takes you down the Chicago River whilst also discovering the architecture of the city and the history behind some of the most iconic buildings.
The 75-minute-long tour passes more than 40 different monuments, as well as a variety of the city’s most well-known bridges.
The commentary is provided by a live guide on board the ship, and there is a bar available for you to purchase refreshments and drinks. This is actually one of the tours I personally like most for first-time visitors. You can also check out my guide on the best boat tours in Chicago .
View Prices & Reviews
3. Wicker Park Walking Food Tour
Like many cities across the United States, Chicago is well known for its growing food culture and Wicker Park is a hub for the culinary scene in the city. This three-hour tour is conducted by a local with extensive knowledge of the best food to try in the city.
You will sample typical Chicagoan food from five different restaurants in the area, all offering their own little slice of the city. This is a great dinnertime tour that will provide you with more than enough food to make a full meal, so come with a full appetite.
4. 90-Minute Mob and Crime Bus Tour
Discover the dark underbelly of Chicago from the safety of a tour bus with this tour, which tackles the history of mobsters and criminals in the city.
You will learn about Al Capone, John Dillinger and many other famous criminals from the city in this tour which lasts around 90 minutes.
You will be shown the different sites that have been influenced by crime in the city, and be able to follow in the footsteps of the most notorious mobsters. You can also delve deeper into the history of the subject at the small mobster museum located in the city.
5. Treasures of Chicago’s Golden Age: 90-Minute Walking Tour
The city experienced a major boom in the late 19th century, which extended right through to the early years of the following century.
This tour takes you around all of the architectural highlights from the era when the city was in major expansion and people were flocking from across the United States to the Windy City. Your skilled local guide will discuss the different factors that influenced Chicago’s expansion, as well as highlight the important historical events that still shape the city to this day.
This tour focuses on the people that built Chicago, giving it a nice personal touch. I highly recommend taking a walking tour on the first day of your visit, it offers plenty of tips on what to do the coming days as well.
6. Chicago Secret Food Tour
Chicago is full of famous restaurants and bars, however this tour aims to take you to the best restaurants that are not well-known by visitors.
You will visit six different spots around the Loop District of Chicago, and learn about the important influence Italian immigrants had on the city. The walking tour takes around three hours to complete, and is paced so you can truly savor all of the dishes you are sampling.
Some drinks are also included. The tour also discusses the local art and architecture in the area, making it a great tour for your first evening in the city.
7. Loop Interior Architecture: 2-Hour Walking Tour
This tour takes you inside the most famous buildings to talk about how the magnificent architecture has been taken indoors.
You will get an extensive tour of the entrances and corridors of these buildings from a knowledgeable local guide, who will discuss the history found within their walls and the lives of the architects who designed them.
You will also be able to check out the underground Pedway System, which has shaped how the rest of the city was designed and changed the lives of locals for decades.
Related reading : Best Things to Do in Downtown Chicago
8. Chicago Hop-on-Hop-off Bus Tour: Classic, Premium or Deluxe
Hop-on-hop-off bus tours are a great way to become acquainted with a new city and gather your bearings. This tour takes you to all of the main sights in the city for you to explore at your own pace.
Audio guides are included to give you more information, and these are available in multiple languages. You can customise your ticket to last either one or two days, and to also include a night bus option. Free WiFi is available on all of the buses, and all guests are given a free bag of Garrett’s Popcorn to snack on whilst enjoying the tour.
I recommend it as a great way to get around the city during your entire visit (there’s 24, 48 and 72 hour option).
9. Gourmet Brunch, Lunch, or Dinner River Cruise
Delight your taste buds with a scrumptious meal prepared by talented chefs, offering a variety of brunch, lunch, or dinner options. Knowledgeable guides provide captivating commentary on the city’s history and architectural wonders, showcasing landmarks like Willis Tower and Navy Pier.
This unique blend of exquisite cuisine, breathtaking scenery, and informative narration promises an unforgettable journey through Chicago’s heart.
Read next : 15 Best Day Trips from Chicago
10. Chicago’s Modern Skyscrapers Guided Walking Tour
Chicago has some of the highest skyscrapers in the city. If one of your main aims for your trip is to check them out, then this walking tour can help you take in the most famous buildings in Chicago.
The local guide will help you understand the history behind all of the skyscrapers, as well as talk at length about the innovations made by architects in the city.
You will learn more about the modernist movement that shaped the city’s skyline and still influences new buildings to this day.
11. Private Helicopter Flight
For the ultimate nighttime tour of the city, this helicopter experience is a fantastic option if you are looking to splurge.
The pilot is fully licensed and experienced, and comes from the local area so is able to provide high-quality commentary about all of the sights you can see from the sky.
From skyscrapers, to the wild waves of Lake Michigan, you can truly see it all from this helicopter experience. All safety equipment is provided and customers are given a short briefing before take-off. Might be an obvious tip but I recommend this experience during a clear day.
12. Navy Pier Centennial Wheel
The Chicago Navy Pier Centennial Wheel offers an exciting experience at one of the city’s most iconic landmarks. With this tour, visitors can enjoy stunning views of Chicago’s skyline and Lake Michigan from the impressive Centennial Wheel. The tour provides various ticket options, allowing guests to customize their experience.
Whether opting for a standard ride, a fast pass, or a private gondola, I highly recommend it to take in breathtaking panoramic view of the city.
Related : 15 Best Hotels in Chicago
13. Bobby’s Bike Hike Chicago: Lakefront Neighborhoods Tour
Featuring some of the wealthiest districts in Chicago, the Lakefront Neighborhoods Tour can provide a relaxed and fulfilling experience during your stay in Chicago.
This tour is done on bikes, helping you to enjoy a more active adventure as well as explore the neighbourhoods at an easy pace. You will be able to check out the local mansions, as well as the Lincoln Park Zoo.
The Lakeside area, where the tour ends, is also a good spot for photo opportunities. This tour accepts all ages, making it a good option for families.
14. Chicago South Side Tour with Optional River Cruise
For visitors more interested in the history of the city, the South Side region is definitely worth a visit.
In this tour, a local guide will talk to you about the founding of the city, and the important landmarks in the South Side region that display the complex and vibrant history of Chicago.
You will also be taken to Jackson Park to enjoy some recreational activities, and to the Art Institute to see the world’s largest collection of Impressionist Art.
This two-hour tour finishes up at the University of Chicago, where you can enjoy the ornate English architecture.
15. Chicago Haunted Bar Tour
Most major American cities have their ghost stories, and Chicago is no exception. Learn all about the macabre past of Chicago and hear captivating ghost stories along the way.
This tour takes you to four different bars across the city, where you can spend some time soaking up the atmosphere and enjoying a local beverage. The tour lasts around two and a half hours, and is great if you are looking for a unique night out in the city.
15 Best Tours in Chicago (by a Local):
- Chicago Skydeck + “The Ledge” Experience Ticket
- Chicago River Architecture Cruise
- Wicker Park Walking Food Tour
- 90-Minute Mob and Crime Bus Tour
- Treasures of Chicago’s Golden Age: 90-Minute Walking Tour
- Chicago Secret Food Tour
- Loop Interior Architecture: 2-Hour Walking Tour
- Chicago Hop-on-Hop-off Bus Tour: Classic, Premium or Deluxe
- Gourmet Brunch, Lunch, or Dinner River Cruise
- Chicago’s Modern Skyscrapers Guided Walking Tour
- Private Helicopter Flight
- Navy Pier Centennial Wheel
- Bobby’s Bike Hike Chicago: Lakefront Neighborhoods Tour
- Chicago South Side Tour with Optional River Cruise
- Chicago Haunted Bar Tour
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