App

Customer support

SGD

Find bookings

Top Picks for Chicago Experiences

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

Trip.com offers 42 Experiences in Chicago

Q: What are the best Experiences in Chicago?

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

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 42 Experiences in Chicago on Trip.com, updated December 7, 2025, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From SGD 17.95 per person, with an average total of SGD 95.68. Choose the option that suits your plan.

With 80 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 79 reviews and a 4.7 rating.

Now on Trip.com: "Bite into Chicago: Discover the City’s Most Iconic Food", a 2-hour adventure in Chicago!

The next available day tour departs on December 8, 2025. Book now to secure your spot!

Chicago Experiences usually take about 2 hours — perfect for a relaxed, immersive experience!

75% of Chicago Experiences now offer English-speaking guides

December 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.

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

Search attractions or local attractions & tours



Trip.comChicago

Experiences

Experiences

Available Today

Available Tomorrow

42 Results for Chicago Experiences

Sort by

Recommended

Chicago River 45-min architecture cruise
Duration: 45–60 mins
English
FromSGD 17.95
Big Bus Chicago Hop-on Hop-off Bus Tour
English
30 booked
FromSGD 46.42
The Chicago Theatre Tour Experience
Duration: 1 hr
English
FromSGD 38.49
Chicago Seadog: Lakefront Speedboat Tour
Duration: 30 mins
FromSGD 54.87
Skyline lake boat tour from Navy Pier
Duration: 45 mins
English
5.0/5
Excellent· 1 review
FromSGD 23.34
Spirit of Chicago dinner cruise
English
FromSGD 149.67
Chicago Premier Lake Michigan brunch cruise
Duration: 120 mins
English
FromSGD 132.87
All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States
FromSGD 19.99
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 79 reviews
FromSGD 98.03
Architecture cruise on the Chicago River from Navy Pier
Duration: 75 mins
English
FromSGD 37.14
Chicago Odyssey dinner cruise
English
FromSGD 250.58
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
FromSGD 57.72
Chicago: Guided Food Tour + Bike or Kayak Rental
Duration: 150 mins
English
FromSGD 109.00
Chicago: Premier Dinner Cruise on Lake Michigan
Duration: 150 mins
FromSGD 226.13
Chicago: Food and Prohibition Architecture Guided Tour
Duration: 5 hrs
English
FromSGD 126.97
Chicago: Canine Cruise
Duration: 90 mins
English
FromSGD 53.87
Lake Michigan: Premier Brunch or Lunch Cruise
Duration: 2 hrs
FromSGD 138.47
Chicago: Chinatown Food & Culture Walking Tour
Duration: 3 hrs
English
FromSGD 102.59
Chicago: Guided Food Tasting + Bike Tour
Duration: 4 hrs
English
FromSGD 126.97
Chicago: Family & Food Guided Bike Tour
Duration: 4 hrs
English
FromSGD 102.59





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

Chicago: River North Walking Food Tour 'Spray Paint & Sip' urban art workshop in Chicago Chicago River 45-Minute Architecture Tour from Magnificent Mile Scenic Chicago Night Tour Chicago River 90-Minute Architecture Tour Chicago: Chinatown Food & Culture Walking Tour Chicago: 2-Hour Kayak Rental from Bridgeport Chicago: Moonlight Paddle Tour on the Chicago River Chicago Favorites Ultimate Food and Walking Tour Chicago: Highlights & Attractions Walking Tour Chicago: Field Museum of Natural History Ticket or VIP Tour Bite into Chicago: Discover the City’s Most Iconic Food Chicago: Loop Neighborhood Guided Walking Tour Millennium Park self-guided walking audio tour in Chicago Chicago: Museum of Ice Cream Entry Ticket

Chicago Activities Chicago Boat Tickets Chicago Group Tours Chicago Yacht Charter Boat Experiences in Chicago Chicago Sports & Adventure Chicago Travel Essentials Water Activities in Chicago Food & Drink in Chicago Chicago Connectivity Solutions Chicago Local Tour Guides Chicago City Pass Chicago Day Tours Chicago Walking Tours Chicago Surfing Guangzhou Spa & Massage Shanghai Activities China Bus Tickets Shenzhen Spa & Massage Shanghai Day Tours Istanbul Spa & Massage Pattaya Spa & Massage Beijing Day Tours Xiamen Spa & Massage Vietnam SIM Card Shanghai must-visit route: Oriental Pearl Radio & Television Tower + Huangpu River night cruise, Chinese group 1-day tour Bus Shared Tranfer From Huanglongjiuzhai Railway Station to Jiuzhaigou|Tikect is available Terracotta Army Tickets Shanghai Romance Park: Performance Ticket Beijing Mutianyu Great Wall 1-day tour · Daily departures at 8/9/10 AM · Round-trip ticket + admission ticket Forbidden City Ticket with Optional Private Guide Or Group Tour Bangkok Space Cube Chengdu city center - Bipenggou direct bus: Group tour with comfortable bus and entrance tickets for an easy and enjoyable visit to the scenic area.One-Day Zhangjiajie Private Tour of Fenghuang and Furong Old Town Private tour from Lijiang: Jade Dragon Snow Mountain + Glacier Park Cableway + Blue Moon Valley

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

★

Reviews: Skyline lake boat tour from Navy Pier

Guest User2025-06-25

When booking on line and getting tickets emailed, information about which doc the boat is on would be great. We live out of state and had no idea which boat it was, where the doc is located we missed our time for departure. Luckily my tickets were honored for a later time.