App

Customer support

USD

Find bookings

Top picks for Chicago Experiences

Q: How many Experiences are available in Chicago on Trip.com?

Trip.com offers 41 Experiences in Chicago

Q: What are the best Experiences in Chicago?

Chicago River 45-min architecture cruise The Chicago Theatre Tour Experience Big Bus Chicago Hop-on Hop-off Bus Tour

Q: What are the top-rated Experiences in Chicago?

Skyline lake boat tour from Navy Pier Bite into Chicago: Discover the City’s Most Iconic Food Chicago River 45-min architecture cruise

Q: How can I contact Trip.com customer support?

Get help anytime, anywhere within 30 seconds Contact customer support

Q: Can I change or cancel my booking?

Change and cancellation policies vary by attractions and tours. Please check the product details page for more information.

Q: How can I get discounted prices?

Ticket prices may vary between weekdays and weekends, as well as during peak and off-peak seasons. When booking with Trip.com, you can also use Trip Coins to get extra savings. For more tips on booking discounted tickets, please visit Trip.com for the latest information.

Discover 41 Experiences in Chicago on Trip.com, updated March 22, 2026, with experiences lasting from 1 to 2 hours. Find the perfect adventure for your day!

With 73 verified reviews, Experiences Chicago boast an average rating of 4.8.

This week's most popular Experiences: "Bite into Chicago: Discover the City’s Most Iconic Food", with 72 reviews and a 4.7 rating.

The next available day tour departs on March 23, 2026. Book now to secure your spot!

Chicago Experiences usually take about 1 hours — perfect for a relaxed, immersive experience!

March is the perfect time to visit Chicago! Choose from Experiences available day tours, including seasonal favorites like Bite into Chicago: Discover the City’s Most Iconic Food.



Search attractions or local attractions & tours

Experiences

Available Today

Available Tomorrow

41 results for Chicago Experiences

Sort by:

Recommended

Chicago River 45-min architecture cruise
Duration: 45–60 mins
English
FromUS$14.00
The Chicago Theatre Tour Experience
Duration: 1 hr
English
FromUS$30.02
Big Bus Chicago Hop-on Hop-off Bus Tour
English
FromUS$36.31
Chicago Seadog: Extreme Thrill Ride
Duration: 30 mins
FromUS$39.30
Chicago Lakefront Fireworks Cruise
Duration: 1 hr
FromUS$44.07
Chicago 2-hour sunset cruise
English
FromUS$20.00
Chicago Seadog: Lakefront Speedboat Tour
Duration: 30 mins
FromUS$42.81
Chicago Premier Lake Michigan brunch cruise
Duration: 120 mins
English
FromUS$103.66
Spirit of Chicago dinner cruise
English
FromUS$116.77
All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States
FromUS$757.34
Chicago Odyssey dinner cruise
English
FromUS$195.50
Skyline lake boat tour from Navy Pier
Duration: 45 mins
English
5.0/5
Excellent· 1 review
FromUS$18.21
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
English
4.7/5
Great· 72 reviews
FromUS$76.48
Architecture cruise on the Chicago River from Navy Pier
Duration: 75 mins
English
FromUS$28.97
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
FromUS$45.04
Chicago: 90-Minute Architecture Tour on the Lake & River
Duration: 90 mins
FromUS$45.04
Architecture cruise on the Chicago River from Michigan Ave
Duration: 75 mins
English
FromUS$28.97
Chicago: Guided Food Tour + Bike or Kayak Rental
Duration: 150 mins
English
FromUS$85.06
Chicago: Canine Cruise
Duration: 90 mins
English
FromUS$42.11
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
Duration: 75 mins
English
FromUS$121.73

Frequently asked questions about Chicago Experiences

How many Experiences are available in Chicago on Trip.com?



What are the best Experiences in Chicago?



What are the top-rated Experiences in Chicago?



How can I contact Trip.com customer support?



Can I change or cancel my booking?



How can I get discounted prices?



Trip.com Picks

Popular Chicago Tours

Best Chicago Experiences

Popular activities

More Popular Destinations

Chicago: Loop Neighborhood Guided Walking Tour Chicago River 45-Minute Architecture Tour from Magnificent Mile Chicago River 90-Minute Architecture Tour Chicago: Museum of Ice Cream Entry Ticket Chicago Favorites Ultimate Food and Walking Tour iFLY Chicago Lincoln Park: First Time Flyer Experience Original Chicago Prohibition Tour Chicago: Field Museum of Natural History Ticket or VIP Tour Chicago: Canine Cruise Chicago: 2-Hour Kayak Rental from Bridgeport Chicago: Moonlight Paddle Tour on the Chicago River Chicago: 45 Minute Architectural Sightseeing Cruise Chicago: Architecture River Cruise from Navy Pier Chicago: Classic Food & Walking Tour with Free Bike or Kayak Chicago: Architecture River Cruise from Michigan Avenue

Chicago Yacht Charter Chicago Travel Essentials Chicago Surfing Chicago Connectivity Solutions Chicago Walking Tours Chicago Group Tours Food & Drink in Chicago Chicago Boat Tickets Chicago Local Tour Guides Boat Experiences in Chicago Chicago Sports & Adventure Water Activities in Chicago Chicago Day Tours Chicago City Pass Chicago Activities Beijing Travel Essentials Sapporo Day Tours Forbidden City Tickets Shanghai Disneyland Tickets Universal Studios Beijing Tickets Shanghai Tower Tickets Canton Tower Tickets Western Australia Esport Events in Feb 2026 Independence day Events in North Sarasota 2025 Kansas City Camps Events in Mar Lake Tōya + Lakeside Farm + Noboribetsu Jigokudani Valley Bazhong Round-Trip: A Day's Stroll Through Encounters with Guangwu Micang La Candelaria Bogotá: Guided Graffiti Tour + Drinks Sintra, Pena Palace & Winery: Day Trip from Lisbon + Wine Tasting & Tapas Colonia Roma: Culinary Experience Discovery Hydra, Poros and Aegina: Full-Day Guided Cruise Tour with Lunch from Athens Delphi: Full-Day Small Group Guided Tour from Athens Mallorca Island Tour: Bus, Train, Tram and Boat Flavors of Philly Food Tour Lisbon: Sintra, Pena Palace, Regaleira, and Cascais Tour Things to do in Hoa Lu District Things to do in Seogwipo Things to do in Jilin Things to do in Atlanta Things to do in Goreme Things to do in Hurghada Things to do in Palma de Mallorca Things to do in Sapa Things to do in Johor Things to do in Indonesia Things to do in Guilin Things to do in Dalat Things to do in Da Nang Things to do in Guangzhou Things to do in Kundasang

Reviews/Trip Moments

★

Reviews: Big Bus Chicago Hop-on Hop-off Bus Tour

Guest User2025-11-06

It’s a nice experience for those who have a short visit to Chicago. One can see the main attractions and city highlights in 24 hrs ticket. 48 hrs ticket only recommended if wishing to use the cruise, otherwise 24 hrs are enough to see the city