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Top picks for Chicago Experiences

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

Trip.com offers 9 Experiences in Chicago

Q: What are the best Experiences in Chicago?

Chicago CityPASS Go City: Chicago Explorer Pass (Discover over 30 top attractions | 360 CHICAGO, Skydeck Chicago & more) Chicago Crime and Mob Bus Tour

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

Chicago: Magnificent Mile Tour With Optional 360 Chicago Chicago: Taste of Chinatown Food and Cultural Walking Tour BIG BUS Chicago hop-on hop-off bus 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.

Discover 9 Experiences in Chicago on Trip.com, updated February 5, 2026, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From HKD 61.15 per person, with an average total of HKD 436.00. Choose the option that suits your plan.

With 3.54k verified reviews, Experiences Chicago boast an average rating of 4.7.

This week's most popular Experiences: "Chicago Crime and Mob Bus Tour ", with 1.597k reviews and a 4.7 rating.

Now on Trip.com: "Chicago: Mob and Crime Bus Tour", a 1-hour adventure in Chicago!

The next available day tour departs on February 6, 2026. Book now to secure your spot!

Chicago Experiences usually take about 1 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.

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9 results for Chicago Experiences

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Chicago CityPASS
English
4.9/5
Excellent· 25 reviews· 256 booked
FromHK$1,093.84
Go City: Chicago Explorer Pass (Discover over 30 top attractions | 360 CHICAGO, Skydeck Chicago & more)
English
4.0/5
Good· 2 reviews· 77 booked
FromHK$656.30
Chicago Crime and Mob Bus Tour
Duration: 90–120 mins
English
4.7/5
Very good· 1.6k reviews
FromHK$382.85
Chicago: Mob and Crime Bus Tour
Duration: 1.5 hrs
English
4.7/5
Very good· 54 reviews
5% off
Limited-time sale
FromHK$363.82HK$382.97
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
English
4.9/5
Excellent· 313 reviews
FromHK$664.04
Chicago: Magnificent Mile Tour With Optional 360 Chicago
Duration: 2–3 hrs
English
5.0/5
Excellent· 2 reviews
5% off
Limited-time sale
FromHK$289.58HK$304.83
Chicago: Field Museum of Natural History Ticket or VIP Tour
English
4.7/5
Very good· 42 reviews
5% off
Limited-time sale
FromHK$215.35HK$226.69
Original Chicago Architecture Interiors Tour: Dazzling Interiors
Duration: 2 hrs
English
4.9/5
Excellent· 1.5k reviews
FromHK$273.46
Chicago: Taste of Chinatown Food and Cultural Walking Tour
Duration: 3 hrs
English
5.0/5
Excellent· 17 reviews
5% off
Limited-time sale
FromHK$630.99HK$664.2
Chicago Explorer Pass: 2 to 7 Attractions including SkyDeck
English
4.7/5
Very good· 13 reviews
5% off
Limited-time sale
FromHK$586.52HK$617.39
BIG BUS Chicago hop-on hop-off bus tour
English
5.0/5
Excellent· 3 reviews· 61 booked
FromHK$282.65
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
FromHK$745.93
Chicago: Craft Brewery Barrel Bus Tour
Duration: 225 mins
English
FromHK$697.83
Alinea, the popular restaurant in Chicago, USA - Restaurant Reservation Service
English
FromHK$61.15
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromHK$234.32
Chicago: Signature Dishes Bike Tour
Duration: 4 hrs
English
FromHK$631.95

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Day tours (104)Travel photography (3)Wi-Fi & SIM cards (27)City pass (8)Visas (8)Transport (2)

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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Trip.com Picks

Popular Chicago Tours

Best Chicago Experiences

Popular Activities

Chicago River 90-Minute Architecture Tour Original Chicago Prohibition Tour Chicago Loop District Food Tour with Deep Dish & Beef Sandwich Chicago: Field Museum of Natural History Ticket or VIP Tour Big Bus Chicago: Hop-on Hop-off Bus Tour Chicago: Museum of Ice Cream Entry Ticket iFLY Chicago Lincoln Park: First Time Flyer Experience Chicago: 45 Minute Architectural Sightseeing Cruise Chicago: Classic Food & Walking Tour with Free Bike or Kayak Chicago: Loop Neighborhood Guided Walking Tour Chicago Favorites Ultimate Food and Walking Tour Chicago Mobs and Haunts Walking Tour Chicago River 45-Minute Architecture Tour from Magnificent Mile Chicago: Highlights & Attractions Walking Tour Chicago: Architecture River Cruise from Michigan Avenue

Chicago Surfing Chicago Connectivity Solutions Chicago Local Tour Guides Food & Drink in Chicago Chicago Group Tours Chicago City Pass Chicago Day Tours Chicago Yacht Charter Chicago Sports & Adventure Boat Experiences in Chicago Chicago Activities Water Activities in Chicago Chicago Boat Tickets Chicago Walking Tours Chicago Travel Essentials Hainan SIM Card China Bus Tickets Guangzhou Spa & Massage Phu Quoc Island SIM Card Sri Lanka SIM Card Shanghai Spa & Massage Xiamen Spa & Massage Chongqing Day Tours Vietnam SIM Card Pattaya Spa & Massage Bus Shared Tranfer From Huanglongjiuzhai Railway Station to Jiuzhaigou Beijing Mutianyu Great Wall 1-day tour · Daily departures at 8/9/10 AM · Round-trip ticket + admission ticket Mutianyu Great Wall With English Speaking Driver Service 2026 Gyeongju Cherry Blossom Marathon Registration Pattaya 6996 Show Kyoto Tango Railway Spirited Away Sea Train Amanohashidate and Ine Boat Houses 1-day Tour with Tickets Included Zhangjiajie Private Tour Day Trip: Fenghuang Ancient Town & Furong Town Beijing Mutianyu Great Wall + Summer Palace 1-Day Tour | No-shoping | In-depth Commentary | Experienced Guide | Round-trip Transfer National Museum of China The Wake Up Club Adult Show Ticket Phuket

Reviews/Trip Moments

★

Reviews: Chicago CityPASS

Guest User2026-01-03

This citypass is good idea for tourist easy to manage. We can visit Chicago in a short time with good memories. I will recommend to my relatives and friends if they visit Chicago.

★

Reviews: Go City: Chicago Explorer Pass (Discover over 30 top attractions | 360 CHICAGO, Skydeck Chicago & more)

Guest User2024-12-07

Easy to use and good choice and savings for short trips

★

Reviews: Chicago Crime and Mob Bus Tour

Guest User2025-12-06

Great tour. Very knowledgeable guide. Highly recommend. I really enjoyed learning so much about the crime history of Chicago.

★

Reviews: Chicago: Mob and Crime Bus Tour

Guest User2026-01-23

My wife and I had an amazing time learning about Chicago's history. And our tour guide was very entertaining and informative. I would highly recommend this activity to anyone visiting Chicago!

★

Reviews: Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

Guest User2024-07-19

Sue was an excellent guide and host…highly recommend. In addition to the food knowledge, Sue showed us some great architectural and unique information about the great city of Chicago.

★

Reviews: Chicago: Magnificent Mile Tour With Optional 360 Chicago

Guest User2025-06-18

Our Mag Mile Tour was great. We learned about the architecture of buildings, design details and history of the area. Our guide Ben was knowledgeable, friendly, full of facts and anecdotes. It was a perfect distance - enough to see the major sites without being too long. We followed with the 360 Chicago at the Hancock. Great tour would highly recommend.

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