All Chicago Tours &amp; Excursions in 2026

Chicago River 90-Minute Architecture Tour

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.

4.7

(9,936)

from $45

Lake Michigan Sunset Cruise in Chicago

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.

4.5

(1,543)

from $45

30 minutesFree Cancellation

Flyover in Chicago

4.8

(549)

from $28

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

(3,169)

from $28

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 $144

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

(16,032)

from $39

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

(1,824)

from $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

(60)

from $24

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

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.

3.9

(2,236)

from $49

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

(1,220)

from $101

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

3 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.

(2,064)

from $85

360 CHICAGO Observation Deck Admission

1 to 4 hoursFree Cancellation

3.9

(1,238)

from $30

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

(136)

from $27

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

(90)

from $44

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

Chicago Crime and Mob Bus Tour

(5,817)

from $57

Special Offer

1 hour 30 minutes to 2 hoursFree Cancellation

Discover the beauty of Chicago at night during a 1.5-hour cruise on the Chicago River and Lake Michigan. Watch the city sparkle as you pass landmarks such as Museum Campus, Willis Tower, Aon Center and the John Hancock Building, and the illuminated waters of Buckingham Fountain. You'll learn about the history of the city from live commentary by your knowledgeable guide as you glide along the waterfront of Chicago.

Chicago By Night River and Lake Cruise

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.

4.5

(306)

from $50

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

3 hoursFree Cancellation

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

(659)

from $80

1 to 30 daysFree Cancellation

3.9

(358)

from $84

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.

Museum of Ice Cream Chicago Admission Ticket

45 minutes to 1 hour 30 minutes

3.4

(419)

from $43

Likely to Sell Out

Chicago Lake and River Architecture 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.

4.7

(2,328)

from $45

Chicago City Minibus Tour

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).

(566)

from $50

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(909)

from $33

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Chicago Favorites Ultimate Food and Walking Tour

4.6

(68)

from $94

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Madeleine_B, May 2026

Greg was our guide for...

Greg was our guide for the food tour and he made the experience so much fun! He was upbeat and knew the history of each restaurant we went to and how it came about! Greg was able to answer all of our questions and is very knowledgable about Chicago! Dress warm if you are not visiting in the warmer months. Walking was fine and only a few steps on the tour. Greg made our tour so much fun!

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 River 90-Minute Architecture Tour

KariRobinson, May 2026

Worth it!

This was such a nice river cruise. We enjoyed getting to see the buildings from the “other side”. Our tour guide provided many interesting facts about the history of the area and buildings. We have visited Chicago many times, and I am glad we finally took the architecture cruise.

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 Center River Cruise aboard First Lady

Kathleen_S, May 2026

Great way to see and learn about Chicago’s great buildings

This 90-minute river cruise provided a fascinating and informative experience about the architecture behind Chicago’s most famous buildings. From the large open top of a boat, we rode the Chicago River seeing magnificent structures that ranged from the early 1900s to today and the transformation of architectural styles from Beaux Arts and Art Deco to postmodernism and contemporary. The sights were just stunning. We were fortunate to have a docent from the Chicago Architecture Center narrate the trip, and she knew everything, adding Chicago history for context. Highly recommended!

Chicago Architecture River Cruise

Carla_M, Apr 2026

Must do tour!

I did this tour last night with my husband and it was fantastic. I recommend going for the sunset option (for us this was around 6.45pm). The city architecture is stunning and our guide Sadie was phenomenal - funny, engaging and full of interesting information with a hint of dry wit! The ride was so smooth thanks to our captain and drink options were nice too. Definitely recommend! Be sure to layer up it gets real cold on the water!

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!