Top Chicago City Tours

Chicago River 90-Minute Architecture Tour

(9,815)

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

from $45

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

3.9

(2,221)

from $44

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

(3,098)

45 minutesFree Cancellation

from $28

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!

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.

Chicago Favorites Ultimate Food and Walking Tour

(2,023)

3 hoursFree Cancellation

from $85

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

(543)

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.

from $50

Chicago Architecture River Cruise

4.8

(15,908)

1 hour to 1 hour 30 minutesFree Cancellation

from $39

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

4.8

(713)

2 to 4 hoursFree Cancellation

from $50

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

4.5

(1,518)

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.

from $45

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.

Chicago's Chinatown Food and Walking Tour

(638)

3 hoursFree Cancellation

from $80

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.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

5.0

(1,562)

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.

from $35

Chicago Architecture Tour: Underground Pedway and the Loop

(441)

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).

from $35

Lake Michigan Skyline Cruise in Chicago

4.4

(905)

30 to 45 minutesFree Cancellation

from $33

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

(5,645)

1 hour 30 minutes

from $57

Total Chicago: From Architecture to Food

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.

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

(1,187)

4 hours 30 minutesFree Cancellation

from $91

Price varies by group size

Chicago Lake and River Architecture Tour

(2,311)

Chicago Crime and Mob Bus Tour

from $45

4.6

(3,267)

1 hour 30 minutes to 2 hoursFree Cancellation

from $49

2 to 8 hoursFree Cancellation

(25)

Chicago City Tours

from $199

Per group

Outside of Italy, few places in the world are as famous for their pizza as Chicago. Eat like a local as you travel off the beaten path to savor the city's best pizza, traveling by bus so you can cover more food hot spots in less time. Discover the science behind ingredient selection and baking as you sample slices from historic pizzerias, and take away plenty of tips to enhance your eating in Chicago.

3 hours 30 minutesFree Cancellation

from $89

5.0

(108)

Downtown Chicago Walking Pizza Tour

2 to 3 hoursFree Cancellation

from $69

Immerse yourself in Chicago's thriving craft beer scene—and visit locals-loved breweries you'd be unlikely to stumble across otherwise—on this half-day brewery tour. Travel in style, and get in the spirit, aboard a traditional Prohibition–style barrel bus. Visit several unique breweries, and go on behind-the-scenes production facility tours. Discover the science behind the brewing process, and enjoy plenty of beer samples throughout the tour.

Chicago Craft Brewery Barrel Bus Tour

(343)

3 hours 45 minutesFree Cancellation

from $100

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.

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

(560)

This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about the city’s past. See the stunning interiors and exteriors of noteworthy buildings and leave with a comprehensive understanding of the city’s downtown.

from $46

Special Offer

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

5.0

(227)

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.

from

$33

$44

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.

Bike Tour of Chicago's Lakefront Neighborhoods

(241)

3 hoursFree Cancellation

from $59

Chicago Walking Tour: Must-See Chicago

(141)

Chicago River 90-Minute Architecture Tour

from $35

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

CHELELL_G, Apr 2026

The best architectural boat cruise in chicago.

The architecture tour was amazing the tour guide was very knowledgeable about the towers when they were built and the history about it .the views are spectacular I highly recommend any one that has the love for architect and skylines to take this tour.

Chicago Architecture River Cruise

Katy_A, Apr 2026

Excellent boat tour

The boat architecture tour did not disappoint! The guide was excellent. He kept things entertaining and informative. The length of about an hour and fifteen minutes was perfect. I had to make a last minute time change and they cheerfully accommodated my request. Highly recommend!

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

Tracey_M, Apr 2026

Brilliant tour of Chicago

A lot of walking but the pace is decent and is totally flat. Some stairs but that’s inside the buildings Dash was my guide, knew loads about the city and made the tour truly interesting! I learnt so much from it and was made extra special as I’d done the boat tour the previous day and had seen the exterior of the buildings but Dash took us inside to view the architecture and extended his knowledge of which was really informative. We rode the train loop and was able to see inside the floors and other architectural features on the sides of the buildings We sampled chocolate brownie, Chicago's hot dog, beef sandwich and deep dish pizza A fantastic tour, so pleased I booked it early on my trip (day 2) as it helped me get my bearings of the city Thanks Dash, truly thankyou for a fab tour !!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Louann_M, Apr 2026

super enjoyable and informative architectural rivercruisr

I followed my maps but when I arrived the boat entrance wasn't marked well, but otherwise the whole experience was great! it was very easy boarding and getting a seat, the staff were all so nice…the tour was just long enough and the gal tour guide was lovely with an english accent, nice to listen to. We learned a lot about Chicago’s history along with timeline of the buildings how they were built and special building materials used, super interesting and well done. it was a lovely day as well which made it so nice, I highly recommend, is my first time to Chicago, great thing to do for all ages!

Chicago Favorites Ultimate Food and Walking Tour

Marsha_M, Apr 2026

5 STARS ASK FOR MICKY. Great entertainment

This food tour is more than just eating! Micky is a top notch guide and you learn the history and legends about Chicago. All the Food was fantastic! There are just enough places that you don't get too much. The nice walk around after each stop was timed well. The entire tour was entertaining. Ask for Micky as your guide.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Cristina_M, Mar 2026

Great tour to learn about Chicago in less than 2h!

The tour was great! We were in Chicago less than 2 days as my colleague and I were coming back from work meetings in other state and we didn't have a lot of time to explore the city on our own. We learn a lot from Spencer (our guide) not only about interiors but also about the history and culture of the city. He also pointed out scenes from famous movies which make it fun! He made us very cool photos and Also he recommended us a few places to have a proper Chicago lunch 😋 and also send us after other recommendations to do. Really enjoyed our time in the city and obviously the tour! Thank you Spencer! 😉

Chicago Architecture Center River Cruise aboard First Lady

Elizabeth_T, Mar 2026

Anthony is the best!

This tour is an absolute must for anyone visiting Chicago. The First Lady is a beautiful boat and all the staff was very professional. Our guide Anthony was incredibly knowledgeable about the architecture and history of every building along the river as well as a lot of history regarding Chicago. His presentation was spectacular!! We will be back and highly recommend to others!

Chicago Night Crimes Tour by Bus

Crystal_M, Oct 2025

Had an amazing time on...

Had an amazing time on this tour!!!! Hearing the stories and stoping at some of the same locations these gangsters and outlaws actually visited , stood, worked and even lost their lives at was quite the experience! The bus driver and tour guide were very professional . Our transportation bus was very nice, clean and comfortable. So glad I took this tour!! Thank you !!!