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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?

iFLY Rosemont (Chicago) Chicago: Signature Dishes Bike Tour Chicago: Craft Brewery Barrel Bus Tour

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

BIG BUS Chicago hop-on hop-off bus tour Sydney Wollongong Newcastle coastal skydiving [with transfers/includes tax + free skydiving certificate/professional 1-on-1 instructor guidance] [Skydive Dubai Official] Dubai Palm Island/Desert Skydiving | Instructor Tandem + Photo/Video Coverage by Photographer & Optional Transfer

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Discover 9 Experiences in Chicago on Trip.com, updated January 18, 2026, with experiences lasting from 1 to 48 hours. Find the perfect adventure for your day!

From MYR 31.62 per person, with an average total of MYR 550.25. Choose the option that suits your plan.

With 161 verified reviews, Experiences Chicago boast an average rating of 4.8.

This week's most popular Experiences: "Skydiving experience in Bangkok, Pattaya, Chiang Mai, and Phuket, Thailand - Skydive Thailand/Dropzone/ThaiSky/Skydive Chiang Mai at 13,000 feet", with 95 reviews and a 4.9 rating.

Now on Trip.com: "Chicago: Signature Dishes Bike Tour", a 4-hour adventure in Chicago!

The next available day tour departs on January 19, 2026. Book now to secure your spot!

Chicago Experiences usually take about 4 hours — perfect for a relaxed, immersive experience!

85% of Chicago Experiences now offer English-speaking guides

January is the perfect time to visit Chicago! Choose from Experiences available day tours, including seasonal favorites like Skydiving experience in Bangkok, Pattaya, Chiang Mai, and Phuket, Thailand - Skydive Thailand/Dropzone/ThaiSky/Skydive Chiang Mai at 13,000 feet.

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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iFLY Rosemont (Chicago)
FromMYR 392.55
Chicago: Signature Dishes Bike Tour
Duration: 4 hrs
English
FromMYR 328.39
Chicago: Craft Brewery Barrel Bus Tour
Duration: 225 mins
English
FromMYR 363.15
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
FromMYR 385.74
BIG BUS Chicago hop-on hop-off bus tour
English
5.0/5
Excellent· 3 reviews· 61 booked
FromMYR 146.76
Cairns Sunlover Reef Cruises 1-day tour [double reef + Ferris wheel/variety show same style/glass bottom boat/diving and snorkeling/buffet lunch/semi-submarine/helicopter sightseeing]
Duration: 4 hrs
4.7/5
Very good· 14 reviews· 309 booked
FromMYR 686.53
Alinea, the popular restaurant in Chicago, USA - Restaurant Reservation Service
English
FromMYR 31.62
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromMYR 121.65
Studio W.I.P. - Uptown Chicago: Spray Paint & Sip Urban Art Workshop
Duration: 90 mins
English
FromMYR 182.47
Restaurant Reservation Service for the Trendy Addison Restaurant in Chicago, USA
English
FromMYR 31.62
Reservation service for the popular Eleven Madison Park restaurant in Chicago, USA
English
FromMYR 31.62
iFLY Chicago (Lincoln Park)
FromMYR 415.08
Chicago CityPASS
English
4.9/5
Excellent· 25 reviews· 261 booked
FromMYR 567.89
SapaParagliding/ParamotorFlight Experience [Highest Adventure with Round-trip Transfer and GoPro]
Duration: 2 hrs
English
FromMYR 385.36
Skydiving experience in Bangkok, Pattaya, Chiang Mai, and Phuket, Thailand - Skydive Thailand/Dropzone/ThaiSky/Skydive Chiang Mai at 13,000 feet
Duration: 8 hrs
English
4.9/5
Excellent· 95 reviews· 845 booked
FromMYR 283.92
Sydney Wollongong Newcastle coastal skydiving [with transfers/includes tax + free skydiving certificate/professional 1-on-1 instructor guidance]
English
5.0/5
Excellent· 3 reviews· 128 booked
FromMYR 887.25
Byron Bay high-altitude ocean view skydiving [Brisbane/Gold Coast transfer + tax included/free skydiving certificate/optional photos and videos]
English
4.6/5
Satisfied· 8 reviews· 125 booked
FromMYR 962.89
[Skydive Dubai Official] Dubai Palm Island/Desert Skydiving | Instructor Tandem + Photo/Video Coverage by Photographer & Optional Transfer
English
5.0/5
Excellent· 3 reviews· 82 booked
FromMYR 3,198.75
Trip.Select
Pattaya Skydiving Experience with FLY WITH DREAM
English
5.0/5
Excellent· 2 reviews· 45 booked
FromMYR 1,121.21
2-Day Explore All Ninh Binh Highlights from Hanoi with local experts
Duration: 48 hrs
English
5.0/5
Excellent· 1 review· 25 booked
FromMYR 480.59

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Frequently asked questions about Chicago Experiences

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

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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 iFLY Chicago Lincoln Park: First Time Flyer Experience Chicago: Loop Neighborhood Guided Walking Tour Chicago: 45 Minute Architectural Sightseeing Cruise Chicago: Museum of Ice Cream Entry Ticket Chicago: Moonlight Paddle Tour on the Chicago River Big Bus Chicago: Hop-on Hop-off Bus Tour Chicago Favorites Ultimate Food and Walking Tour Millennium Park self-guided walking audio tour in Chicago Chicago Mobs and Haunts Walking Tour Original Chicago Prohibition Tour Chicago: Field Museum of Natural History Ticket or VIP Tour Chicago River 45-Minute Architecture Tour from Magnificent Mile Chicago: 2-Hour Kayak Rental from Bridgeport Chicago River 90-Minute Architecture Tour

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Reviews/Trip Moments

★

Reviews: BIG BUS Chicago hop-on hop-off bus tour

Guest User2025-11-06

It’s a nice experience for those who have a short visit to Chicago. One can see the main attractions and city highlights in 24 hrs ticket. 48 hrs ticket only recommended if wishing to use the cruise, otherwise 24 hrs are enough to see the city

★

Reviews: Cairns Sunlover Reef Cruises 1-day tour [double reef + Ferris wheel/variety show same style/glass bottom boat/diving and snorkeling/buffet lunch/semi-submarine/helicopter sightseeing]

Guest User2025-06-03

It's pretty good, including round-trip boat tickets to Emerald Island, lunch and snorkeling. There is plenty of time to play and the service is also very good!