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Top picks for Chicago Experiences

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

Trip.com offers 38 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?

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Discover 38 Experiences in Chicago on Trip.com, updated February 6, 2026, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From IDR 126,391.00 per person, with an average total of IDR 1,119,959.30. Choose the option that suits your plan.

With 3.579k verified reviews, Experiences Chicago boast an average rating of 4.8.

This week's most popular Experiences: "Chicago Crime and Mob Bus Tour ", with 1.602k 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 7, 2026. Book now to secure your spot!

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

86% 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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38 results for Chicago Experiences

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Recommended

Chicago CityPASS
English
4.9/5
Excellent· 25 reviews· 256 booked
FromIDR 2,369,483
Go City: Chicago Explorer Pass (Discover over 30 top attractions | 360 CHICAGO, Skydeck Chicago & more)
English
4.0/5
Good· 2 reviews· 77 booked
FromIDR 1,421,690
Chicago Crime and Mob Bus Tour
Duration: 90–120 mins
English
4.7/5
Very good· 1.6k reviews
FromIDR 829,320
Chicago: Mob and Crime Bus Tour
Duration: 1.5 hrs
English
4.7/5
Very good· 54 reviews
5% off
Limited-time sale
FromIDR 786,500IDR 827,895
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
English
4.9/5
Excellent· 313 reviews
FromIDR 1,438,446
Chicago: Field Museum of Natural History Ticket or VIP Tour
English
4.7/5
Very good· 42 reviews
5% off
Limited-time sale
FromIDR 465,457IDR 489,955
Chicago: Magnificent Mile Tour With Optional 360 Chicago
Duration: 2–3 hrs
English
5.0/5
Excellent· 2 reviews
5% off
Limited-time sale
FromIDR 625,978IDR 658,925
Original Chicago Architecture Interiors Tour: Dazzling Interiors
Duration: 2 hrs
English
4.9/5
Excellent· 1.5k reviews
FromIDR 592,371
Chicago: Taste of Chinatown Food and Cultural Walking Tour
Duration: 3 hrs
English
5.0/5
Excellent· 17 reviews
5% off
Limited-time sale
FromIDR 1,364,151IDR 1,435,949
Chicago Explorer Pass: 2 to 7 Attractions including SkyDeck
English
4.7/5
Very good· 13 reviews
5% off
Limited-time sale
FromIDR 1,267,876IDR 1,334,607
BIG BUS Chicago hop-on hop-off bus tour
English
5.0/5
Excellent· 3 reviews· 61 booked
FromIDR 597,013
City Cruises Chicago: Christmas Eve Gourmet Dinner Cruise
Duration: 2.5 hrs
4.6/5
Satisfactory· 5 reviews
5% off
Limited-time sale
FromIDR 3,125,179IDR 3,289,663
Chicago River 45-min architecture cruise
Duration: 45–60 mins
English
FromIDR 231,261
Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier
Duration: 1.5 hrs
English
FromIDR 960,567
Architecture cruise on the Chicago River from Michigan Ave
Duration: 75 mins
English
FromIDR 478,544
Chicago Odyssey Lake Michigan dinner cruise
English
FromIDR 2,145,767
Festive Chicago food and walking tour
English
FromIDR 165,021
Architecture cruise on the Chicago River from Navy Pier
Duration: 75 mins
English
FromIDR 483,004
Restaurant Reservation Service for the Trendy Addison Restaurant in Chicago, USA
English
FromIDR 126,391
Reservation service for the popular Eleven Madison Park restaurant in Chicago, USA
English
FromIDR 126,391
Alinea, the popular restaurant in Chicago, USA - Restaurant Reservation Service
English
FromIDR 126,391
Chicago Odyssey dinner cruise
English
FromIDR 3,229,388
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
FromIDR 1,541,861
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromIDR 495,393
Chicago ultimate food experience
Duration: 120 mins
English
FromIDR 1,238,896
River North food tour
English
FromIDR 1,304,970
Chicago Premier Lake Michigan brunch cruise
Duration: 120 mins
English
FromIDR 1,928,878
Chicago favorites food walking tour
Duration: 180 mins
FromIDR 1,321,324

Explore top experiences

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Day tours (102)Travel photography (2)Wi-Fi & SIM cards (23)City pass (11)Visas (3)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: Classic Food & Walking Tour with Free Bike or Kayak Chicago Mobs and Haunts Walking Tour iFLY Chicago Lincoln Park: First Time Flyer Experience Original Chicago Prohibition Tour Chicago: Loop Neighborhood Guided Walking Tour Chicago: Field Museum of Natural History Ticket or VIP Tour Chicago: Highlights & Attractions Walking Tour Chicago: 45 Minute Architectural Sightseeing Cruise Chicago River 45-Minute Architecture Tour from Magnificent Mile Chicago: Architecture River Cruise from Michigan Avenue Chicago: Museum of Ice Cream Entry Ticket Chicago Loop District Food Tour with Deep Dish & Beef Sandwich Big Bus Chicago: Hop-on Hop-off Bus Tour Chicago River 90-Minute Architecture Tour Chicago Favorites Ultimate Food and Walking Tour

Chicago Activities Chicago Day Tours Chicago Connectivity Solutions Water Activities in Chicago Chicago Yacht Charter Chicago Group Tours Chicago Boat Tickets Chicago Surfing Food & Drink in Chicago Chicago City Pass Chicago Sports & Adventure Chicago Walking Tours Chicago Local Tour Guides Chicago Travel Essentials Boat Experiences in Chicago 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: Field Museum of Natural History Ticket or VIP Tour

Guest User2026-01-26

The Field Museum was definitely exciting and fun. It was pretty cool seeing dinosaurs up close and learning about different cultures as well as animals. The weekends get pretty crowded with families in attendance. I would recommend visiting during the week for a quieter visit.

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