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

Trip.com offers 45 Experiences in Chicago

Q: What are the best Experiences in Chicago?

BIG BUS Chicago hop-on hop-off bus tour Chicago Architecture Sightseeing Cruise Experience [Departing from Michigan Avenue]|Depart from Navy Pier All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States

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

BIG BUS Chicago hop-on hop-off bus tour Chicago Loop District Food Tour with Deep Dish & Beef Sandwich Bite into Chicago: Discover the City’s Most Iconic Food

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.

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Discover 45 Experiences in Chicago on Trip.com, updated December 7, 2025, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From JPY 2,359.00 per person, with an average total of JPY 11,960.25. Choose the option that suits your plan.

With 403 verified reviews, Experiences Chicago boast an average rating of 4.7.

This week's most popular Experiences: "Chicago Loop District Food Tour with Deep Dish & Beef Sandwich", with 313 reviews and a 4.9 rating.

Now on Trip.com: "Chicago Architecture Sightseeing Cruise Experience [Departing from Michigan Avenue]|Depart from Navy Pier", a 1-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 1 hours — perfect for a relaxed, immersive experience!

60% of Chicago Experiences now offer English-speaking guides

December is perfect for visiting Chicago! Choose from Experiences available day tours, including seasonal hits like Chicago Loop District Food Tour with Deep Dish & Beef Sandwich.

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

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45 Results for Chicago Experiences

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BIG BUS Chicago hop-on hop-off bus tour
English
5.0/5
Excellent· 1 review· 41 booked
FromJPY 5,475
Chicago Architecture Sightseeing Cruise Experience [Departing from Michigan Avenue]|Depart from Navy Pier
Duration: 1.5 hrs
English
FromJPY 8,768
All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States
FromJPY 2,359
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.3/5
Good· 6 reviews
FromJPY 4,538
Chicago: 90-Minute Architecture Tour on the Lake & River
Duration: 90 mins
FromJPY 6,814
Chicago Seadog: Lakefront Speedboat Tour
Duration: 30 mins
FromJPY 6,478
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
Duration: 75 mins
English
FromJPY 24,027
Chicago: Premier Dinner Cruise on Lake Michigan
Duration: 150 mins
FromJPY 30,836
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
FromJPY 6,814
Chicago: Food and Prohibition Architecture Guided Tour
Duration: 5 hrs
English
FromJPY 13,491
Chicago: Skyline Lake Tour
Duration: 45 mins
English
FromJPY 5,120
Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch
Duration: 2 hrs
FromJPY 14,714
Lake Michigan: Premier Brunch or Lunch Cruise
Duration: 2 hrs
FromJPY 20,488
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
4.9/5
Excellent· 313 reviews
FromJPY 13,466
Chicago: Chinatown Food & Culture Walking Tour
Duration: 3 hrs
English
FromJPY 10,901
Chicago: Guided Food Tasting + Bike Tour
Duration: 4 hrs
English
FromJPY 13,491
Chicago: Guided Food Tour + Bike or Kayak Rental
Duration: 150 mins
English
FromJPY 12,868
Chicago: Family & Food Guided Bike Tour
Duration: 4 hrs
English
FromJPY 12,111
Chicago: Food Tour + Bike or Kayak Rental
Duration: 5 hrs
English
FromJPY 14,874
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 83 reviews
FromJPY 11,572

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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?

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How can I contact Trip.com customer support?



Can I change or cancel my booking?



How can I get discounted prices?

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Trip.com Picks

Popular Chicago Tours

Best Chicago Experiences

Popular Activities

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

Chicago Day Tours Chicago Local Tour Guides Chicago Yacht Charter Chicago Group Tours Chicago Travel Essentials Chicago Boat Tickets Chicago Activities Chicago Connectivity Solutions Chicago Walking Tours Boat Experiences in Chicago Chicago Surfing Water Activities in Chicago Chicago City Pass Chicago Sports & Adventure Food & Drink in Chicago 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 User2025-09-21

The app was very convenient as it told me where the bus was. It said the bus was every 30 minutes, but it seemed to come a little earlier.

★

Reviews: Chicago Full Day Bike Rental

Guest User2024-09-02

Very well organized! Well located for access to Lakefront Trail! We took the Confort Hybrid bikes and 4 very happy adults! I recommend without hesitation:-)