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Top Picks for Chicago Experiences

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

Trip.com offers 25 Experiences in Chicago

Q: What are the best Experiences in Chicago?

BIG BUS Chicago hop-on hop-off bus tour Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States

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

BIG BUS Chicago hop-on hop-off bus tour Chicago: River North Walking Food Tour Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

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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 25 Experiences in Chicago on Trip.com, updated December 2, 2025, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From AUD 15.29 per person, with an average total of AUD 111.44. Choose the option that suits your plan.

With 431 verified reviews, Experiences Chicago boast an average rating of 4.8.

This week's most popular Experiences: "Chicago Loop District Food Tour with Deep Dish & Beef Sandwich", with 313 reviews and a 4.9 rating.

Now on Trip.com: "Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier", a 1-hour adventure in Chicago!

The next available day tour departs on December 3, 2025. Book now to secure your spot!

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

70% of Chicago Experiences now offer English-speaking guides

December is the perfect time to visit Chicago! Choose from Experiences available day tours, including seasonal favorites like Chicago Loop District Food Tour with Deep Dish & Beef Sandwich.

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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25 Results for Chicago Experiences

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BIG BUS Chicago hop-on hop-off bus tour
󱩳Enjoy the beautiful scenery of Chicago on a convenient open-top double-decker bus.
English
5.0/5
Excellent· 3 reviews· 60 booked
FromAU$ 55.33
Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier
󱩳Board the Chicago Architecture River Cruise and admire the stunning skyline
Duration: 1.5 hrs
English
FromAU$ 89.01
All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States
󱩳Global language translation allows you to communicate without worries no matter where you are, and start your health journey with peace of mind.
FromAU$ 23.95
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromAU$ 45.89
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
4.9/5
Excellent· 313 reviews
FromAU$ 136.17
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 86 reviews
FromAU$ 117.02
Chicago River 45-min architecture cruise
󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Duration: 45–60 mins
English
FromAU$ 21.42
Architecture cruise on the Chicago River from Navy Pier
󱩳Enjoy panoramic skyline views from along the Chicago River
Duration: 75 mins
English
FromAU$ 44.33
Chicago favorites food walking tour
󱩳Taste your way through the Windy City's finger-licking food scene
Duration: 180 mins
FromAU$ 122.39
Chicago Premier Lake Michigan brunch cruise
󱩳Enjoy a buffet-style brunch with freshly prepared entrees, salads and desserts
Duration: 120 mins
English
FromAU$ 178.66
Chicago Odyssey dinner cruise
󱩳Enjoy delicious and sophisticated lakefront dining
English
FromAU$ 299.11
River North food tour
󱩳Tease your taste buds and join this tour in the River North and Wicker Park neighborhoods
English
FromAU$ 120.87
Chicago ultimate food experience
󱩳Get a taste of Chicago's most famous food in one of the city's most historic neighborhoods
Duration: 120 mins
English
FromAU$ 114.75
Architecture cruise on the Chicago River from Michigan Ave
󱩳Admire Chicago's amazing urban architecture from the Chicago River
Duration: 75 mins
English
FromAU$ 44.33
Festive Chicago food and walking tour
󱩳Wander through Millennium Park, State Street and The Loop
English
FromAU$ 15.29
Chicago Odyssey Lake Michigan dinner cruise
󱩳Admire the skyline of Chicago
English
FromAU$ 198.75
Chicago:Milwaukee City Highlights Day Trip with Brewery Tour
󱩳Immerse yourself in the world of motorcycles at the Harley-Davidson Museum
Duration: 8 hrs
English
FromAU$ 191.25
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
󱩳Chinese-speaking driver at a fixed price (services available in Chinese and English)
English
FromAU$ 142.87
Chicago: Taste of Chinatown Food Walking Tour
󱩳Learn about the vibrant history of Chicago's Chinatown
Duration: 2.5 hrs
4.8/5
Great· 21 reviews
5% off
FromAU$ 123.50AU$ 130.01
Chicago: River North Walking Food Tour
󱩳Explore the best hidden gourmet gems and off-the-beaten path spots
Duration: 3 hrs
5.0/5
Excellent· 1 review
5% off
FromAU$ 143.85AU$ 151.43

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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

Popular Chicago Tours

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Chicago Favorites Ultimate Food and Walking Tour Bite into Chicago: Discover the City’s Most Iconic Food Chicago: Moonlight Paddle Tour on the Chicago River Chicago: 2-Hour Kayak Rental from Bridgeport Chicago: Chinatown Food & Culture Walking Tour Chicago: Field Museum of Natural History Ticket or VIP Tour Chicago: Museum of Ice Cream Entry Ticket Chicago: River North Walking Food Tour Scenic Chicago Night Tour Chicago: 360 Chicago Observation Deck Sip and View Ticket 'Spray Paint & Sip' urban art workshop in Chicago Millennium Park self-guided walking audio tour in Chicago Chicago River 90-Minute Architecture Tour Chicago: Loop Neighborhood Guided Walking Tour Chicago River 45-Minute Architecture Tour from Magnificent Mile

Chicago Walking Tours Chicago Group Tours Chicago Travel Essentials Chicago Local Tour Guides Chicago Activities Chicago SIM Card Food & Drink in Chicago Chicago Boat Tickets Chicago Restaurant Discounts Chicago Visa Application Services Chicago Shopping Discounts Chicago Bus Tickets Boat Experiences in Chicago Chicago Connectivity Solutions Shanghai Activities China Bus Tickets Shanghai Day Tours Istanbul Spa & Massage Pattaya Spa & Massage Shenzhen Spa & Massage Beijing Day Tours Vietnam SIM Card Chongqing Day Tours Japan SIM Card Shanghai must-visit route: Oriental Pearl Radio & Television Tower + Huangpu River night cruise, Chinese group 1-day tour Bus Shared Tranfer From Huanglongjiuzhai Railway Station to Jiuzhaigou|Tikect is available Forbidden City Ticket with Optional Private Guide Or Group Tour 6996 Show,79 Show,89 Show,99 Show Pattaya Ticket Mutianyu Great Wall With English Speaking Driver Service Xi'an "THE GREAT QIN" Stage Show Ticket - An Epic Artistic Feast Featuring the Terracotta Warriors Terracotta Army Tickets Private tour from Lijiang: Jade Dragon Snow Mountain + Glacier Park Cableway + Blue Moon Valley Shanghai Romance Park: Performance Ticket From Khao Sok: Private Longtail Boat Tour at Cheow Lan Lake

Reviews/Trip Moments

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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: Chicago Full Day Bike Rental

Guest User2025-10-18

Easy process, great communication, rode the 7 speed city comfort bikes to Evanston and back. A very enjoyable ride. Appreciated the locks included in the rental.

★

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: Bite into Chicago: Discover the City’s Most Iconic Food

Guest User2025-07-29

The walking food tour was so great. Love the city views of the Chigao food scene. Rich, our tour guide was amazing. We kept a gggood walking pace while privvibg some city history info. He was entertaining, funny and knowledgeable about the city, the restaurants we visited and the foods we ate. He was better than Google! He made us feel welcomed and part of the Chicago family. Thank you Rich, Cinnamon, Erik, Tyler and Maria

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