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Top Chicago Activities and Things to Do

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 Loop District Food Tour with Deep Dish & Beef Sandwich

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 Chicago's Original Dazzling Architectural Interiors Tour

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Q: Can I change or cancel my booking?

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

From TRY 341.82 per person, with an average total of TRY 2,573.69. Choose the option that suits your plan.

With 3.977k verified reviews, Experiences Chicago boast an average rating of 4.7.

This week's most popular Experiences: "Chicago Crime and Mob Bus Tour ", with 1.602k reviews and a 4.7 rating.

Now on Trip.com: "Chicago Loop District Food Tour with Deep Dish & Beef Sandwich", a 3-hour adventure in Chicago!

The next available day tour departs on February 10, 2026. Book now to secure your spot!

Chicago Experiences usually take about 3 hours — perfect for a relaxed, immersive experience!

95% 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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Recommended

Chicago CityPASS
󱲌
25 consecutive positive reviews
English
4.9/5
Excellent· 25 reviews· 256 booked
FromTRY 6,107.35
Go City: Chicago Explorer Pass (Discover over 30 top attractions | 360 CHICAGO, Skydeck Chicago & more)
󱩳Save up to 50% vs buying individual tickets Go at your own pace with 30 days validity from your first attraction visit Perfect for ticking a few firm favourites off your bucket list
Book now for today
English
4.0/5
Good· 2 reviews· 77 booked
FromTRY 3,664.41
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
󱲌
79 consecutive positive reviews
Free cancellation
Duration: 3 hrs
4.9/5
Excellent· 313 reviews
FromTRY 3,707.60
Alinea, the popular restaurant in Chicago, USA - Restaurant Reservation Service
󱩳Exquisite flavors with consistently high quality
English
FromTRY 341.82
Reservation service for the popular Eleven Madison Park restaurant in Chicago, USA
󱩳Exquisite flavors with consistently high quality
English
FromTRY 341.82
Restaurant Reservation Service for the Trendy Addison Restaurant in Chicago, USA
󱩳Exquisite flavors with consistently high quality
English
FromTRY 341.82
Chicago Crime and Mob Bus Tour

91.4% of travelers recommend
Free cancellation
Book now for today
Duration: 90–120 mins
4.7/5
Very good· 1.6k reviews
FromTRY 2,137.58
Chicago: Magnificent Mile Tour With Optional 360 Chicago
󱩳Admire Art Deco, Beaux-Arts, and neoclassical architecture.
Free cancellation
Duration: 2–3 hrs
5.0/5
Excellent· 2 reviews
5% off
Limited-time sale
FromTRY 1,616.77TRY 1,701.87
Chicago: Field Museum of Natural History Ticket or VIP Tour

90.5% of travelers recommend
Free cancellation
English
4.7/5
Very good· 42 reviews
5% off
Limited-time sale
FromTRY 1,202.29TRY 1,265.57
Chicago: Taste of Chinatown Food and Cultural Walking Tour
󱩳Discover the traditions, symbols, and stories behind Chinatown's rich heritage.
Free cancellation
Book now for today
Duration: 3 hrs
5.0/5
Excellent· 17 reviews
5% off
Limited-time sale
FromTRY 3,523.58TRY 3,709.04
Chicago's Original Dazzling Architectural Interiors Tour
󱩳Explore unknown beautiful spaces that even locals walk by every day
Free cancellation
Book now for today
Duration: 2 hrs
5.0/5
Excellent· 8 reviews
5% off
Limited-time sale
FromTRY 1,451.18TRY 1,527.56
Chicago Explorer Pass: 2 to 7 Attractions including SkyDeck
󱩳Discover the secrets of the universe at Adler Planetarium, and more!
Free cancellation
English
4.7/5
Very good· 13 reviews
5% off
Limited-time sale
FromTRY 3,275.19TRY 3,447.57
Original Chicago Architecture Interiors Tour: Dazzling Interiors
󱲌
39 consecutive positive reviews
Free cancellation
Book now for today
Duration: 2 hrs
4.9/5
Excellent· 1.5k reviews
FromTRY 1,526.84
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
󱩳Flat rate for Chinese-speaking or English-speaking drivers (bilingual service provided)
Free cancellation
English
FromTRY 4,169.82
Chicago: Signature Dishes Bike Tour
Free cancellation
Duration: 4 hrs
FromTRY 3,534.21
Chicago: Craft Brewery Barrel Bus Tour
Free cancellation
Duration: 225 mins
FromTRY 3,911.72
Detroit Pistons Tickets
󱩳Guaranteed entry, genuine and reliable.
Duration: 3 hrs
FromTRY 2,597.76
Paula Deen's Lumberjack Feud Supper Show- ALL U CAN EAT
Free cancellation
Duration: 90 mins
4.0/5
Good· 284 reviews
FromTRY 2,630.09
Turtle Beach Power Snorkeling Adventure
󱲌
100 consecutive positive reviews
Free cancellation
Duration: 2 hrs
5.0/5
Excellent· 189 reviews
FromTRY 5,801.55
BIG BUS Chicago hop-on hop-off bus tour
󱩳Enjoy the beautiful scenery of Chicago on a convenient open-top double-decker bus.
Book now for today
English
5.0/5
Excellent· 3 reviews· 61 booked
FromTRY 1,465.70

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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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Trip.com Picks

Top Tours in Chicago

Best Experiences in Chicago

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Instituto de Arte de Chicago: Entrada sin colas + Visita guiada semiprivada Chicago: Crucero al atardecer con guía de 90 minutos Chicago: Visita sin colas al Instituto de Arte con guía Chicago: Guided Food Tasting + Bike Tour Chicago: Food and Prohibition Architecture Guided Tour Chicago: Crucero turístico arquitectónico de 45 minutos Chicago Night Crimes Bus Tour: Criminals, Mobsters and Gangsters Chicago: Recorrido guiado a pie por el barrio Loop Chicago round-trip|Dubuque Town + Galena Town + Grant Park Chicago: American Writers Museum Flexible Date Entry Ticket Chicago River 45-Minute Architecture Tour from Magnificent Mile Chicago: Underground Pedway & the Loop Guided Walking Tour Chicago: Tapas & Flamenco Dinner in Ukrainian Village Recorrido gastronómico y a pie definitivo por los lugares favoritos de Chicago iFLY Chicago Lincoln Park: First Time Flyer Experience

Wellness & Spa in Chicago Chicago Travel Essentials Chicago Day Tours Chicago Classes Chicago Local Tour Guides Chicago Spa & Massage Chicago Airport Services Food & Drink in Chicago Boat Experiences in Chicago Chicago Cultural Experience Chicago Travel Services Chicago Visa Application Services Chicago Transportation Chicago Shopping Discounts Chiang Mai City Pass Food & Drink in Hua Hin Hua Hin Travel Essentials Bangkok Local Tour Guides Thailand City Pass Nagoya Sports & Adventure Nagoya Travel Essentials Xi'an Shopping Discounts Fujikawaguchiko Visa Application Services Boat Experiences in Osaka Excursión de un día al Parque Nacional Hell's Gate y paseo opcional en barco por el lago Naivasha.3 Hour shared Cinque Terre tour + Swim Stops at Secluded Beaches!Tzoumerka villages tour All in One Day Konorchek Canyon Issyk Kul Lake and Burana Tower Isla Tortuga, paraíso con snorkel incluido Excursión de un día a las cascadas de Materuni y a las aguas termales de Chemka Galveston Mansions and Murder Walking Tour MÁS VENDIDO: Excursión de lujo de un día en crucero por la bahía de Ha Long - Todo Incluido St Louis Premium Driving Tour With St Louis Arch & River Cruise Rome Golf Cart Tour: Highlights of the Eternal City

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 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.