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

Trip.com offers 9 Experiences in Chicago

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

Chicago: Magnificent Mile Tour With Optional 360 Chicago BIG BUS Chicago hop-on hop-off bus tour Chicago: Secret Interiors Architecture Walking Tour

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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 9 Experiences in Chicago on Trip.com, updated February 28, 2026, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From CAD 10.80 per person, with an average total of CAD 64.66. Choose the option that suits your plan.

With 4.703k verified reviews, Experiences Chicago boast an average rating of 4.6.

This week's most popular Experiences: "Chicago Crime and Mob Bus Tour ", with 1.621k reviews and a 4.7 rating.

Now on Trip.com: "Chicago Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters", a 2-hour adventure in Chicago!

The next available day tour departs on March 1, 2026. Book now to secure your spot!

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

100% of Chicago Experiences now offer English-speaking guides

February is the perfect time to visit Chicago! Choose from Experiences available day tours, including seasonal favorites like Chicago Crime and Mob Bus Tour .

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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9 results for Chicago Experiences

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Chicago Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters
Duration: 2 hrs
English
FromCAD 66.79
City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise
Duration: 2–2.5 hrs
English
4.8/5
Very good· 18 reviews
5% off
Limited-time sale
FromCAD 109.90CAD 115.69
Chicago: Secret Interiors Architecture Walking Tour
Duration: 2 hrs
English
4.9/5
Excellent· 214 reviews
5% off
Limited-time sale
FromCAD 46.48CAD 48.93
Chicago: Signature Dishes Bike Tour
Duration: 4 hrs
English
FromCAD 122.65
Alinea, the popular restaurant in Chicago, USA - Restaurant Reservation Service
English
FromCAD 10.80
Reservation service for the popular Eleven Madison Park restaurant in Chicago, USA
English
FromCAD 10.80
Chicago: Food Tour + Bike or Kayak Rental
Duration: 5 hrs
English
FromCAD 148.83
Chicago: Magnificent Mile Tour With Optional 360 Chicago
Duration: 2–3 hrs
English
5.0/5
Excellent· 2 reviews
5% off
Limited-time sale
FromCAD 50.58CAD 53.25
Chicago Crime and Mob Bus Tour
Duration: 90–120 mins
English
4.7/5
Very good· 1.6k reviews
FromCAD 66.78
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
English
4.9/5
Excellent· 313 reviews
FromCAD 115.83
Chicago: 48-hour Hop-on Hop-off Tour and 360 CHICAGO Deck
English
4.4/5
Good· 5 reviews
5% off
Limited-time sale
FromCAD 108.93CAD 114.67
Original Chicago Prohibition Tour
Duration: 4 hrs
English
FromCAD 75.01
Big Bus Chicago: Hop-on Hop-off Bus Tour
English
FromCAD 61.37
Book after inquiry/Route 66 Willis Tower Robie House Lincoln Park Airport in Chicago, USA/Point-to-point car service/Tour guide and driver/Private car service
English
FromCAD 131.64
Restaurant Reservation Service for the Trendy Addison Restaurant in Chicago, USA
English
FromCAD 10.80
Studio W.I.P. - Uptown Chicago: Spray Paint & Sip Urban Art Workshop
Duration: 90 mins
English
FromCAD 61.37
BIG BUS Chicago hop-on hop-off bus tour
English
5.0/5
Excellent· 3 reviews· 64 booked
FromCAD 45.81
Chicago: Craft Brewery Barrel Bus Tour
Duration: 225 mins
English
FromCAD 135.82
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromCAD 40.88
Trip.Select
Carnival Magic Phuket Standard Seat|Royal Seat|Dinner Buffet|Multiple Option available
English
4.8/5
Very good· 8 reviews· 430 booked
FromCAD 79.07
Pattaya Chang Thai Thappraya Safari Elephant Village|Elephant riding|ATV|Horseback riding|Live shooting|Off-road vehicle|Jungle flying
Duration: 2 hrs
English
4.5/5
Satisfied· 4 reviews· 149 booked
FromCAD 15.49
Phang Nga Province Khao Lak Sky Rock Adventure: Jungle Zipline/Sky Roller Coaster Experience
English
FromCAD 40.82
Bangkok Chao Phraya River Cruise - Buffet + Music Performance-Luxury cruise tour
Duration: 4 hrs
English
4.4/5
Good· 254 reviews· 7.3k booked
FromCAD 37.24
Sofitel Macau at Ponte 16 Buffet | Mistral Restaurant Lunch/Dinner Buffet
English
4.4/5
Good· 666 reviews· 5.4k booked
FromCAD 29.35
JW Marriott Hotel Macau Urban Kitchen Lunch/Dinner Buffet
English
4.6/5
Satisfied· 794 reviews· 6.8k booked
FromCAD 43.55
Trip.Select
The Luxury White Dinner Cruise New Boat Departs from ICONSIAM Pier Bangkok
English
4.4/5
Good· 113 reviews· 3.7k booked
FromCAD 55.61
Trip.Select
Harbour Grand Hong Kong | Harbour Grand Café | Buffet lunch/ Buffet dinner
Duration: 2 hrs
English
4.3/5
Good· 631 reviews· 4.2k booked
FromCAD 48.47
Trip.Select
Shanghai Palace Banquet: Immersive experience of a royal feast thousands of years ago (fine Food and Beverages+ dance performance + Qin Dynasty historical and cultural experience + optional Clothes & Accessories and makeup)
Duration: 80 mins
English
4.6/5
Satisfied· 50 reviews· 1.9k booked
FromCAD 39.71

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Frequently asked questions about Chicago Experiences

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

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What are the best Experiences in Chicago?

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What are the top-rated Experiences in Chicago?

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How can I contact Trip.com customer support?

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Can I change or cancel my booking?

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How can I get discounted prices?

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Reviews/Trip Moments

★

Reviews: City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise

Guest User2026-02-02

Great experience, receiving a voucher due to us not being able to go out. But just the experience, food, staff and captain were amazing! Our server Jamie gave us the best experience. We will be visiting again in the summer!

★

Reviews: Chicago: Secret Interiors Architecture Walking Tour

Guest User2026-02-16

The tour was incredibly fun!!! Our guide, Annie, has an unbelievable amount of detailed knowledge; I learned so much about the wonderful city of Chicago! The two hours were packed with new impressions of the city's history and architecture. I highly recommend it!!!