All Chicago Tours &amp; Excursions in 2026

Chicago River 90-Minute Architecture Tour

1 hour 30 minutesFree Cancellation

4.7

(9,971)

from USD 45

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.

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,060)

from USD 39

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

from USD 144

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

3 hoursFree Cancellation

Marvel at Chicago's iconic architecture and lakefront from a unique perspective with this 30-minute immersive ride. With drone footage, helicopter-mounted cameras, and other custom media, Flyover Chicago creates the sensation of flying above and through the city to take in its highlights from above. Get up close to details atop the highest skyscrapers and learn about Chicago's history and cityscape during the ride.

(2,072)

from USD 85

30 minutesFree Cancellation

Flyover in Chicago

4.8

(555)

from USD 28

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

1 hour 30 minutesFree Cancellation

4.5

(1,544)

from USD 45

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 Walking Tour: Food, History & Architecture

4 hours 30 minutesFree Cancellation

Price varies by group size

(1,228)

from USD 101

Likely to Sell Out

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

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.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

4.7

(3,186)

from USD 28

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

4.3

(1,826)

from USD 44

Take your Chicago experience to new heights with a ride on the iconic Navy Pier Centennial Wheel. Step into a climate-controlled gondola and enjoy sweeping views of the city skyline, Lake Michigan, and Navy Pier from 200 feet above the water. This family-friendly attraction is perfect for visitors of all ages looking to add a fun and memorable highlight to their day in downtown Chicago. Admire the scenery as you complete multiple rotations, and enjoy easy access to restaurants, shops, and lakeside entertainment right on Navy Pier. Tickets offer flexibility to ride any time during open hours.

Chicago's Navy Pier Centennial Wheel Ticket

15 minutesFree Cancellation

4.2

(61)

from USD 24

Housed in the only remaining building from the 1893 World's Fair, Griffin MSI is a Chicago must-see. When visiting the largest science museum in the Western Hemisphere, you'll experience a 40-foot tornado, climb aboard a World War II German submarine, take a run in a human-sized hamster wheel, descend into an Illinois coal mine, board a 727 hanging from the ceiling and much more! Griffin MSI is not a place where you walk around quietly and observe. You get involved in the fun — and learn — by doing. Just a few miles from downtown with convenient underground parking.

Griffin Museum of Science and Industry Admission

2 to 4 hoursFree Cancellation

4.7

(16)

from USD 26

The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers. Located in the heart of downtown on Michigan Avenue, the observatory is steps away from other top Chicago attractions. It will be the high point (literally) of your Chicago trip! Upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. The Sip menu includes a rotating selection of beer, wine and cocktails. Once onsite, you can purchase tickets to TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. You may also choose to upgrade your Sip and View ticket from the Sip Menu to the Elevated Menu for an additional $8. *TILT not included in purchase

360 Chicago Observation Deck Sip and View Ticket

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.

4.1

(91)

from USD 44

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

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.

(5,863)

from USD 57

Chicago City Minibus Tour

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.

(568)

from USD 50

Original Chicago Architecture Interiors Tour: Dazzling Interiors

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

5.0

(1,610)

from USD 35

1 to 30 daysFree Cancellation

3.9

(359)

from USD 84

Discover one of Chicago’s top architectural marvels when you explore Frank Lloyd Wright’s UNESCO-listed Frederick C. Robie House, located right on the University of Chicago’s campus. Considered a masterpiece of Prairie School architecture, the building is famed for its cantilevered roof and rich wood details. Save money when you book tickets to the house in advance; call ahead to reserve a space on one of the museum’s frequent, small-group public tours.

Frank Lloyd Wright Robie House Admission

1 hourFree Cancellation

4.2

(137)

from USD 27

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!

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

Chicago Crime and Mob Bus Tour

3.9

(2,238)

from USD 49

Special Offer

1 hour 30 minutes to 2 hoursFree Cancellation

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

360 CHICAGO Observation Deck Admission

1 to 4 hoursFree Cancellation

3.9

(1,239)

from USD 30

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

3 hoursFree Cancellation

Chicago Perfume Making Classes on Magnificent Mile

(665)

from USD 80

You get to name your new Exclusive Scent

1 hour 15 minutesFree Cancellation

4.8

(61)

from USD 85

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

3 hours 45 minutesFree Cancellation

Enter a land of sugar and adventure with admission to Chicago’s Museum of Ice Cream. Immerse yourself in a vibrant world of interactive exhibits, including sprinkle-filled pools, whimsical selfie spots, and exclusive ice cream sampling stations offering seasonal flavors. Whether you’re an art lover or a dessert enthusiast, this playful, family-friendly experience promises fun and memories for all. Avoid disappointment by booking your preferred time.

(348)

from USD 100

Museum of Ice Cream Chicago Admission Ticket

45 minutes to 1 hour 30 minutes

3.4

(422)

from USD 43

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago River 90-Minute Architecture Tour

Maranda_L, May 2026

Great place to start your Chicago adventure

The tour was amazing! Very interesting to learn so much about the city and then go explore , having an early time was great for that! And the tour guide was excellent! Plenty of space for viewing on the boat , free to walk around and have to say even with a full tour no one was in the way or hard to see around still plenty of space to sit or move around at your leisure! Would highly recommend! Also the accommodation was super helpful our flight became delayed which would of had us miss our tour time , I called an hour before our scheduled time and they got us moved to the next tour the same day which was amazing!

Chicago Favorites Ultimate Food and Walking Tour

Anne_G, May 2026

Awesome tour - highly...

Awesome tour - highly recommend!! We ate a lot so great value for the money (deep dish pizza, beef sandwich, Chicago dog, popcorn and a brownie) We walked a lot (so wear comfortable shoes). The tour guide was great - fun with interesting stories about the city. We saw sights on both sides of the river and had plenty of time at Cloud Gate (The Bean) and the other stops to take pictures. Fun excursion - do it!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Jasmine_A, May 2026

The best boat tour ever !

Had an amazing time on this boat tour in Chicago! The views of the city skyline were absolutely beautiful, especially from the water. The tour guide was super friendly, knowledgeable, and made the whole experience even more enjoyable. Definitely a great way to see the city and learn a little about Chicago along the way. Highly recommend for anyone visiting or even locals looking for a fun outing!

Chicago By Night River and Lake Cruise

Crawford_W, May 2026

Phenomenal.

Very memorable. Every staff member performed top tier, from the bartenders to the host who informed us of the Chicago buildings! And we can’t forget the greeters, the staff who was on the street directing us to where we’ll be boarding. And last, but never least, the captain who steered so beautifully 🙏🏾❤️💯! Everyone gets AAAAA’s!

Chicago Architecture River Cruise

Christine_G, May 2026

Excellent way to learn and see Chicago’s beautiful buildings

Don was an outstanding docent on the Chicago Architecture Cruise. He was knowledgeable, engaging, and had a great way of bringing the city’s history and architecture to life. His enthusiasm made the tour both entertaining and informative. We left with a much deeper appreciation for Chicago thanks to his Insights and storytelling

Chicago Architecture Center River Cruise aboard First Lady

James_H, May 2026

Wayne is amazing!

We took the 90-minute cruise with Wayne this morning and loved every moment. Wayne was the BEST. So knowledgeable about the city history and the architecture—he shared info in an enthusiastic yet laid-back way, and was very personable and funny (but not silly). We highly recommend this cruise and Wayne!

Chicago Crime and Mob Bus Tour

Kathleen_S, May 2026

Outstanding tour!

Very informative and entertaining. The guide provided nonstop, wide-ranging details while also keeping humor at the forefront. We stood in the alley where John Dillinger was gunned down, saw where the St. Valentine’s Day Massacre occurred, and visited a small museum dedicated to Chicago’s most notorious characters. Highly recommended!

Lake Michigan Sunset Cruise in Chicago

Marla_K, Apr 2026

Bring a blanket or warm...

Bring a blanket or warm jacket. It may look like a nice day out but on the water its chilly. Bring a backpack for water or a beverage and snack. Other then that we had a great time and it was nice to see the city all lit up. So beautiful and so relaxing. If your a drinker they have a full bar. They also have some snacks. Once out on the channel you can walk about the boat. Plenty of seating.

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Amena_S, Apr 2026

Top tier experience

It was amazing from start to finish. Very aesthetically pleasing and service and food was top tier. Our server Heather was a perfect 10 across the board. Her recommendations, her spirit, her genuine energy was a breath of fresh air. She helped us with food selections, which were amazing down to photo opportunities. She even led us to the amazing bartender Keisha who made the best bottomless mimosas to say the least. We had to stop by the bar to let Ms Keisha know how well she mixed those cocktails. This was truly an amazing birthday brunch experience. Great way to start my birthday!!!

Chicago Lake and River Architecture Tour

Melanie_B, Oct 2025

Great nighttime tour of Chicago River

My friend and I had a great time on this river cruise! We did the 6:45pm tour in October, so it did get dark, but the views were gorgeous and our tour guide Lucas was informative. It was a pretty packed boat, so make sure to get there early, in order to get in line and get a good spot. Still recommend this tour!