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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Discover 25 Experiences in Chicago on Trip.com, updated November 21, 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 November 22, 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

November 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