Top Chicago City Tours

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

3.9

(2,291)

from $49

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Explore Chicago's legendary architecture and history.

Chicago River 90-Minute Architecture Tour

(10,277)

from $45

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Chicago City Minibus Tour

(597)

from $50

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Join us in the daytime or evening for City lights and breathtaking views

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

(3,314)

from $28

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

(16,358)

from $39

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

Lake Michigan Sunset Cruise in Chicago

Chicago Sunset Tour by Open-Top Bus with Live Guide

4.5

(1,593)

from $45

4.1

(174)

from $39

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!

Chicago Favorites Ultimate Food and Walking Tour

(2,146)

from $85

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.6

(3,383)

from $49

A picture of Chicago Chinatown’s landscape shows vibrant streets, iconic arches, and rich culture—everything guests explore on our Chinatown Food Tours. Food Tours in Chinatown bring it all to life.

Immerse yourself in one of Chicago's most vibrant neighborhoods—and head off the tourist trail to discover sights and bites many visitors miss—on this small-group Chinatown food and walking tour. With your guide in the lead, learn about the cuisine of different regions of China, and discover the history of Chicago's Chinatown. Along the way, enjoy a generous array of tastings, from dim sum to Sichuan cuisine and beyond.

Chicago's Chinatown Food and Walking Tour

(718)

from $80

Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riverfront landmarks to groundbreaking modern skyscrapers. Explore the Loop’s civic, financial, and architectural core, admire world-renowned towers, and experience Chicago’s most celebrated public spaces. This small-group tour offers a comprehensive introduction to Chicago’s skyline, history, and urban design, concluding with a panoramic skyline view before returning guests to the original pickup point. Ideal for first-time visitors and architecture enthusiasts alike. Explore Chicago’s iconic riverfront skyscrapers and historic bridges See legendary architecture including Willis Tower and Marina City Discover the heart of Chicago’s financial, civic, and architectural power Pass by Millennium Park and spend time at Cloud Gate (The Bean) Enjoy a panoramic Chicago skyline view, included for all guests

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

(16)

from $48

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Original Chicago Architecture Interiors Tour: Dazzling Interiors

5.0

(1,692)

from $35

Chicago River 90-Minute Architecture Boat Tour

(1,703)

from $37

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

(2,350)

from $45

Downtown Chicago Walking Pizza Tour

2 to 3 hoursFree Cancellation

5.0

(115)

from $69

Skyline Queen showcasing the Chicago Skyline!

See the Second City from the water with a sightseeing cruise along the Chicago River and the Lake Michigan shoreline, offering a unique perspective of towering skyscrapers and historic architecture. This tour offers stories about the city’s history and culture as you pass by Chicago's landmarks, museums, and buildings. Capture unforgettable images of the city skyline from Lake Michigan, ensuring a unique look at Chicago, perfect for all ages.

Chicago Sightseeing River and Lake Cruise

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

(605)

from $46

Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO

(6,249)

from $57

1 to 30 days

4.0

(361)

from $84

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

Chicago City Tour with Architecture River Cruise Option

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

Chicago Night Crimes Tour by Bus

(727)

from $50

Stop off the bus at Chicago Landmark Building with Prohibition Era History

2 hours to 2 hours 30 minutesFree Cancellation

Explore the hidden side of Downtown Chicago—and see sights that even many locals miss—on a small-group walking tour of the Pedway (an underground network of tunnels that connects Chicago buildings) and the vibrant Loop. Ideal for architecture fans, this tour includes insider stories and landmarks you wouldn't spot on your own—plus a chance to see Windy City icons like the Picasso Statue and Millennium Park.

(497)

from $55

Chicago Architecture Tour: Underground Pedway and the Loop

Chicago Architecture Tour: Underground Pedway and the Loop

Chicago City Private Tours

(500)

from $35

2 to 8 hoursFree Cancellation

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

(30)

from $199

Per group

Total Chicago: From Architecture to Food

Chicago in a Day Walking Tour: Food, History & Architecture

4 hours 30 minutesFree Cancellation

Price varies by group size

(1,287)

from $101

Smiles ear to ear as you ride our Chicago Bike Tour through scenic Lakefront Neighborhoods. Fresh air, open paths, and lake views make this the ultimate Bicycle Tour in Chicago.

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

Bike Tour of Chicago's Lakefront Neighborhoods

Chicago in a Day Walking Tour: Food, History & Architecture

(248)

from $59

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Top Attractions in Chicago

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What are people saying about Chicago

Michelle_M, Jun 2026

I enjoyed my walking...

I enjoyed my walking tour. Rich was great. He reached out via text to introduce himself before the tour. I liked that we did the architecture part of the tour first then did the food tasting the second half. I liked that we were given time to take photos and Rich even offered to take our photos. Rich was amazing and had great energy. I would recommend this tour. It was a great way to see a bit of the city and sample some must try food Chicago is known for.

Chicago Night Crimes Tour by Bus

Bobbie_W, Jun 2026

Chicago Tour Brought Gangster History to Life

The Chicago Nighttime gangster brought Capone & Dillinger to life. Interesting well prepared tour. Rich history and fascinating stops at unique locations that tie to the history. Tour guide was skillful upbeat and carried the tour with energy and engagement

Chicago River 90-Minute Architecture Tour

Macy_S, Jun 2026

Our guide Tess was...

Our guide Tess was wonderful! She clearly knows Chicago’s history well, and I really enjoyed her storytelling! The only thing is, completely outside of the boat company’s control, is there is a thing that fully shoots water at you from the fountain!! So just be wary if you have anything with you that you may have to close/cover it up. None of us were soaked, but it was pretty annoying. This happened about 90% through the tour at the fountain, and our guide said she had never had that happen before! Other than that (again, nothing towards the company!), I really thought this was a well done tour!

Lake Michigan Sunset Cruise in Chicago

Cindi_B, Jun 2026

Gorgeous sunset views!!

Gorgeous sunset views! (We never actually saw the sunset…) A sister trip that was just magical! Between the sites, the refreshments, and the company, was just perfect! Note: THIS IS NOT AN ARCHITECTURE TOUR! The poor tour guide said it three times and people still asked, lol! She was hilarious too though, very entertaining!!

Chicago Architecture River Cruise

Ladiny_P, Jun 2026

A nice tour around Downtown Chicago

Booked this experience last minute to see the sites that downtown Chicago has to offer. The tour was only an hour, but time really flew by. Unfortunately, due to the other passengers having side conversations, I barely was able to hear the guide explain the different buildings and its significance. Overall a great experience.

Chicago Architecture Center River Cruise aboard First Lady

Jennifer_L, Jun 2026

Recommended! A great way to learn about Chicago!

This was a really interesting cruise/tour! You might be a little unsure because it's called the"architecture" cruise, but it was incredibly interesting, even if you're not into architecture! There was so much history and humor. We had a great time. Our tour guide, Bob, was really informative. He knew so much about the history of Chicago as well as the actual architecture.

Chicago Crime and Mob Bus Tour

Lauren_E, Jun 2026

Very cool tour!

Great tour guide about mob history. However, it's a good idea to fact check. For example Al Capone did not have a funeral service at Holy name cathedral.He was denied a service because of his dark history of a murder and bullet hole in structure. The service was in Miami and he was buried in Chicago We did go back to the Harry Carrey restaurant and the food was excellent!

Chicago Favorites Ultimate Food and Walking Tour

Megan_A, Jun 2026

Great guide, delicious food!

My husband and I really enjoyed our food tour with Elizabeth as our guide! We learned a lot and had some delicious food and it was just a really enjoyable time. We also took advantage of the two free hours of bike rental that is included and really loved biking along the Lakeshore after the tour. Highly recommend both!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Sylvia_L, Jun 2026

A must for first time visitors!

45 minute boat tour was the perfect length unless you are on one of the evening boat tours. The sun was starting to get too strong after 35 minutes. The tour guide was fun and knowledgeable. The architecture itself was breathtaking but the history behind each building and it's architect made it so much more interesting than just a beautiful structure. Highly recommend!

Chicago's Chinatown Food and Walking Tour

Betsy_S, Jun 2026

I loved this tour.

Our guide, York was fantastic! Extremely knowledgeable in the history of Chinatown as well as Chicago in general. The food was great and I was happily surprised by the portion sizes. You won’t leave hungry, that is for sure. Great experience. Leave yourself enough time to explore more of Chinatown on your own once the tour is through. Highly recommend this tour!

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Jean_C, May 2026

fantastic indoor architecture tour

Wonderful tour of indoor architecture; some walking between buildings, so be prepared for weather. Our enthusiastic guide Adam was very knowledgeable and passionate about the places we visited. We learned a LOT about the history of Chicago! He made the tour really fun. The buildings were stunningly gorgeous inside.

Chicago City Minibus Tour

Fatmata_B, May 2026

This trip was great. He...

This trip was great. He had alot of knowledge about Chicago to pass on and he was very easy to reach. He went far and beyond giving me directions and reaching out on where i should park or how to get to the destination. The tour guy was great and he made it to all the stops even with the traffic that was available .