All Chicago Tours &amp; Excursions in 2026

30 minutesFree Cancellation

Flyover in Chicago

(609)

from $28

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

(10,302)

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

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.

(3,326)

from $28

from $144

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

(1,854)

from $44

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

(16,391)

from $39

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

(1,266)

from $30

Chicago's Navy Pier Centennial Wheel Ticket

15 minutesFree Cancellation

4.2

(69)

from $24

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

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

3.9

(2,299)

from $49

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

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.

4.5

(1,598)

from $45

Total Chicago: From Architecture to Food

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

4 hours 30 minutesFree Cancellation

4.9

(1,289)

from $101

Price varies by group size

Chicago River Ghost & Dark History Night Cruise

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chicago River while hearing chilling tales of disasters, infamous criminals, and eerie legends tied to the city’s past. This relaxed river cruise blends atmospheric storytelling with some of the best nighttime views of Chicago’s renowned skyline and landmarks. Grab a drink from the onboard bar, settle in, and let the city’s shadowy history unfold as you cruise through the heart of downtown. By the end of the journey, you’ll have experienced Chicago’s skyline in a whole new way—while uncovering the chilling events, legends, and mysteries that shaped the city. Please arrive 30 minutes in advance!

Chicago River Ghost & Dark History Night Cruise

4.1

(141)

from $46

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

3 hoursFree Cancellation

4.9

(2,149)

from $85

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).

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(927)

from $33

See Chicago's magnificent skyline at night!

Chicago 3D Fireworks Cruise

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

4.2

(242)

from $52

360 Chicago Observation Deck Sip and View Ticket

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.

4.1

(96)

from $44

Museum of Ice Cream Chicago Admission Ticket

Museum of Ice Cream Chicago Admission Ticket

45 minutes to 1 hour 30 minutes

3.4

(431)

from $43

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

4.9

(724)

from $80

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

(2,351)

from $45

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.6

(3,390)

from $49

Delve into the world of natural history with admission to Chicago’s Field Museum. Choose general admission or upgrade to visit one or more special exhibits. Spend as long as you like exploring the museum's extensive collection of artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Also take advantage of daily tours led by knowledgeable Field Museum docents, free with admission.

Field Museum of Natural History Admission Tickets

4 hoursFree Cancellation

4.6

(540)

from $29

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

1 to 30 days

4.0

(361)

from $84

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks on this scenic lunch cruise along Lake Michigan. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.

City Cruises Chicago: Signature Lunch Cruise on 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.

4.0

(363)

from $63

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Chicago River 45-Minute Architecture Tour from Magnificent Mile

5.0

(1,696)

from $35

1 2 3

...

Top Attractions in Chicago

1 / 2

Attractions

What are people saying about Chicago

LeAnn_A, Jun 2026

Summer morning

We had a great time, with Tess as our tour guide. We did the 9:30 AM 45 minute tour. It was a toasty summer day in June, so I'm glad we did the earlier tour and had a few clouds. Tess was extremely knowledgeable, and was a lovely narrator of the architectural styles, the city history, and other interesting bits about Chicago. I've done the architecture tour before, and will definitely do it again.

Chicago Crime and Mob Bus Tour

Victor_C, Jun 2026

Great tour by our guide, Tess.

Great tour with lots of information on the beautiful Chicago River. Tess, our tour guide, was great and covered a lot of ground (water?) in a short amount of time. Our boat was full and we had to sit on the side which was not ideal -- get there at least 15-20 minutes before departure time to get a good seat.

Chicago River 90-Minute Architecture Tour

Ronald_O, Jun 2026

Chicago architecture done right

The narrator is wonderful. She does an awesome job. The cruise is about the right amount of time and our narrator knew everything about the history of Chicago and went in a great detail explaining the buildings. The year is built how tall it was the square feet that is huge designed who built it and the significance of it for the Chicago history

Chicago Sightseeing River and Lake Cruise

REGINA_E, Jun 2026

Good choice for cruise

River cruise into Lake Michigan with an amazing guide who knew the entire history of Chicago. He points out a lot of buildings and other sights. Before you can go into the lake you have to wait for the water to settle which is interesting in itself. You will have a great view of Chicago from the water.

Chicago By Night River and Lake Cruise

Agnes_G, Jun 2026

This was one of the best...

This was one of the best boat tours we experienced. The tour was well organized, the boat was well maintained. Chicago is a beautiful city, the night view was spectacular. Olivia did an excellent job presenting the highlights and history of the buildings. We particularly appreciate her presentation of the architectural backgrounds of the shoreline buildings. If you only have time to take one boat tour in the city I would highly recommend this one.

Chicago Architecture Center River Cruise aboard First Lady

Nikki_M, Jun 2026

Amazing tour on the First Lady

Incredible tour. We were luckily to also have fantastic weather. Claudia, our guide, was knowledgeable and entertaining. Our family joked we could have listened to her teach us about the city for 2 more hours easily. We learned so much and never were bored. My sons are ages 16, 14 and 11 and were engrossed the entire tour. The boat was clean and the staff was friendly. 10/10 would not only recommend but would do it again!

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

Eleisa_W, Jun 2026

Highlight of my trip

I would recommend going at the 9 pm showing just to get the experience at nighttime! I went to the morning one and it was beautiful, but I think the lights of chicago’s architecture would be beautiful to see. The guide was super kind and lovely to listen to, he seemed like he really loves his job. The entire staff was warm and friendly, I’ll definitely do this again just for the pace of scenery. Thank you so much

Lake Michigan Skyline Cruise in Chicago

Anisha_S, Jun 2026

Relaxing Ride

The skyline tour was exactly what I needed after a day of eating and walking about. I was able to book the tour an hour before, which worked for my itinerary and it was affordable. I liked that it is a double decker boat and got to experience the tour from top deck. The day was beautiful and perfect for a tour. The boat was clean, looked presentable, offered cocktails and small snacks(for purchase) and staff were friendly. The tour offered ok views. I was able to capture pictures of the Chicago skyline. My fav part of the ride was how relaxing it was. I would do it again and be sure to nap the next time lol.

Chicago Lake and River Architecture Tour

Clint_W, Apr 2026

Perfect Chicago Experience — River + Lake Views in One Trip

Absolutely loved this architecture boat cruise! Getting to see both the Chicago River and Lake Michigan in one trip was the perfect combo. The views of the skyline from the water are incredible, and the guide did a great job sharing interesting history without it feeling overwhelming. Super relaxing, well-organized, and a great way to experience the city—highly recommend!