Top Chicago City Tours

Chicago River 90-Minute Architecture Tour

(10,928)

from $45

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

See Chicago your way with flexible hop-on hop-off tickets designed to suit every sightseeing style. Explore the Windy City at your own pace, hopping off to visit top attractions such as Millennium Park, Navy Pier, the Magnificent Mile, and the Chicago Riverwalk while enjoying onboard commentary that adds context to what you see. Perfect for first-time visitors or those short on time, this tour offers flexibility and ensures you don’t miss any of Chicago’s highlights. You can also upgrade your experience to enjoy extra sightseeing time and a panoramic sunset tour for unforgettable skyline views.

(3,586)

from $28

Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus

Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus

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.

3.9

(2,394)

from $49

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,982)

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.

360 panoramic views of the Chicago skyline at sunset.

Lake Michigan Sunset Cruise in Chicago

4.5

(1,688)

from $45

Chicago River 90-Minute Architecture Boat Tour

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.

4.8

(1,889)

from $37

Chicago City Minibus Tour

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.

(646)

from $50

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

Chicago Crime and Mob Bus Tour

(2,302)

from $85

1 hour 30 minutes to 2 hoursFree Cancellation

4.6

(3,547)

from $49

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

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.

(2,438)

from $45

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

5.0

(1,796)

from $35

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(948)

from $34

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

Discover more of Chicago beyond downtown with this convenient South Side open-top shuttle transfer. Travel from central Chicago to some of the city’s most important cultural and historic destinations, including Jackson Park, the Obama Presidential Center campus, and the Griffin Museum of Science & Industry. Enjoy an easy ride south without arranging taxis, rideshares, or public transit connections. The shuttle first stops near the Obama Presidential Center and Jackson Park, giving you access to one of Chicago’s most historic lakefront spaces. Explore the area at your own pace, take photos, or continue your visit independently. The route also serves the Griffin Museum of Science & Industry, one of Chicago’s most popular attractions and one of the largest science museums in the world. This is a great option for travelers who want a simple, affordable way to visit Chicago’s South Side highlights from downtown. Choose a one-way transfer or an all-day ticket for added flexibility.

(795)

from $80

Roundtrip Shuttle to South Side and Obama Presidential Center

Roundtrip Shuttle to South Side and Obama Presidential Center

30 minutesFree Cancellation

4.3

(12)

from $10

Chicago Walking Tour: Must-See Chicago

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

(165)

from $35

Special Offer

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

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.

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

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.

(7,059)

from $57

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

(723)

from $46

Explore Chicago's buzzing food scene—and see some of its best-known landmarks on the way—on this two-in-one walking tour. The small group size offers are more intimate experience as you stroll around the vibrant Loop area, spotting highlights from the Willis Tower to the Rookery building. Indulge in a variety of famous Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches.

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

Price varies by group size

(1,007)

from $85

Experience Chicago in Style with Our Luxury City Sightseeing Minibus Tour. Indulge in the ultimate Chicago adventure on our top-rated, luxury sightseeing minibus tour. This 2-hour, expertly guided experience takes you through the vibrant heart of the city in a sleek, climate-controlled minibus designed for comfort and class. Marvel at iconic skyline views and the shimmering waters of Lake Michigan from panoramic windows, and enjoy curated photo stops at the city's most breathtaking landmarks. With engaging stories from your private guide and an intimate, upscale atmosphere, this tour offers an unmatched blend of elegance and exploration. Please note, infants 0-3 years old must sit on a lap.

Luxury Minibus Chicago City Tour

Chicago All Day Water Taxi

(16)

from $65

20 minutesFree Cancellation

3.3

(7)

from $36

Downtown Chicago Walking Pizza Tour

2 to 3 hoursFree Cancellation

5.0

(127)

from $69

From deep-dish to hot dogs, taste Chicago Classic Dishes on our Chicago Food & Bike Tour. Ride by Bicycle, learn the stories, and savor every stop on the best Food & Bike Tour in Chicago.

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

4 hours 30 minutesFree Cancellation

Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.

(767)

from $89

Special Offer

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Lake Michigan Sunset Cruise in Chicago

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Susanna_M, Sep 2026

Fun way to see the city from the lake

Not an architecture tour so don’t take this if that is what you’re looking for. A great way to see the sites at night. A very enjoyable evening and Bobby are guide was knowledgeable and available to everyone for any question they may have had! Highly recommend this tour!

Chicago Crime and Mob Bus Tour

Su_O, Sep 2026

Best Crime Tour in Town

Our first time in Chicago and my daughter really wanted to see the crime tour. We had an amazing time driving thru Chicago and listing to the stories. We stopped in 3 locations and was able to get out of the bus and explore. See the actual "crime scene" We did it on Sunday morning, so traffic and places were not as crowded. TOTALLY WORTH IT

Chicago River 90-Minute Architecture Tour

Robert_B, Sep 2026

Great experience! The...

Great experience! The tour guide was funny, informative and made it even better. Can’t remember her name exactly(Alana?) red headed woman. The views were incredible and it was a lot of fun seeing the city lit up at night. Would definitely recommend to anyone!

Chicago Architecture Center River Cruise aboard First Lady

Michael_B, Sep 2026

Chicago Architectural Center River Cruise aboard the First Lady

We found the Chicago Architectural Center River Cruise aboard the First Lady to be the best way to view Chicago's stunning and historic architecture for the vantage point of the Chicago River. The narration was provided by a knowledgeable, volunteer docent, who gave a credible and factually accurate commentary. Although the boat is multilevel, the tour is conducted from the open-air, top deck. The audio is also played inside on the main deck; however, the interior deck lacks the visual vantage perspectives. The tour occurs rain or shine, so plan accordingly. Great value for the money

Chicago Favorites Ultimate Food and Walking Tour

Michelle_B, Sep 2026

Highly Recommend

We’ve done at least a dozen food tours across the U.S. and were very impressed with this Chicago tour. Our guide, Gabe, did an awesome job; sharing plenty of city knowledge, humor, and keeping the tour flowing. The food stops themselves were a great balance of Chicago favorites. Even our 10 yr old son enjoyed it. We would definitely recommend!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Evelynn_T, Sep 2026

Recommended by locals

I went with my friend in town and boyfriend. I am a southside native and looking for a touristy thing to do in the city. It was 95 degrees out but we still had so much fun. The breeze helped and they sell drinks. Would recommend for anyone looking to learn more about our beautiful city.

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

mazndene, Aug 2026

Great tour guide and experience.

Great tour, David our guide was very knowledgeable. He took us to places we never would have looked at but WOW. Food was a real bonus it will fill you up. The popcorn stop was an eye opener who would have thought cheese and caramel would be so tasty 😂. Would definitely recommend this tour Chicago is an amazing city and thanks to David it was such an enjoyable experience.

Chicago Night Crimes Tour by Bus

Wesley_S, Jul 2026

Fascinating Tour!

What an interesting, and fascinating tour. The rich history of Chicago's mob crimes, while off putting to some, makes for a unique tour experience. If you enjoy learning about crime history, or even heard of Al Capone and the beer wars, Dillinger, Nitty, this is the tour for you. The guide was great, plus it's at night so you get to see the downtown at night which is stunning.

Lake Michigan Skyline Cruise in Chicago

Stanley_A, Jul 2026

We had a great experience...

We had a great experience on the Skyline Cruise in Chicago. The staff was extremely friendly and welcoming from start to finish. The boat ride was smooth, and the views of the city were absolutely beautiful. We also enjoyed learning about Chicago’s landmarks and history throughout the tour. I would highly recommend this cruise to anyone visiting Chicago—it’s a relaxing, scenic, and educational experience!