Top Picks for Chicago Experiences

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

Trip.com offers 36 Experiences in Chicago

Q: What are the best Experiences in Chicago?

BIG BUS Chicago hop-on hop-off bus tour City Cruises Chicago: Christmas Eve Gourmet Dinner Cruise Chicago River 45-min architecture cruise

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

BIG BUS Chicago hop-on hop-off bus tour Chicago: Classic Food and Walking Tour with Free Bike/Kayak Chicago in a Day: Food, History & Architecture Walking Tour

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Discover 36 Experiences in Chicago on Trip.com, updated November 25, 2025, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From NZD 13.64 per person, with an average total of NZD 120.99. Choose the option that suits your plan.

With 44 verified reviews, Experiences Chicago boast an average rating of 4.8.

This week's most popular Experiences: "Chicago in a Day: Food, History & Architecture Walking Tour", with 24 reviews and a 4.8 rating.

Now on Trip.com: "City Cruises Chicago: Christmas Eve Gourmet Dinner Cruise", a 2-hour adventure in Chicago!

The next available day tour departs on November 26, 2025. Book now to secure your spot!

Chicago Experiences usually take about 2 hours — perfect for a relaxed, immersive experience!

80% 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 in a Day: Food, History & Architecture Walking Tour.

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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36 Results for Chicago Experiences

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󱩳Enjoy the beautiful scenery of Chicago on a convenient open-top double-decker bus.
BIG BUS Chicago hop-on hop-off bus tour
English
5.0/5
Excellent· 3 reviews· 61 booked
FromNZD 64.52
󱩳Admire city landmarks such as Navy Pier and Willis Tower while cruising.
City Cruises Chicago: Christmas Eve Gourmet Dinner Cruise
Duration: 2.5 hrs
4.6/5
Satisfactory· 5 reviews
5% off
Limited-time sale
FromNZD 337.05NZD 354.79
󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Chicago River 45-min architecture cruise
Duration: 45–60 mins
English
FromNZD 24.95
󱩳Board the Chicago Architecture River Cruise and admire the stunning skyline
Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier
Duration: 1.5 hrs
English
FromNZD 103.61
󱩳Admire Chicago's amazing urban architecture from the Chicago River
Architecture cruise on the Chicago River from Michigan Ave
Duration: 75 mins
English
FromNZD 51.62
󱩳Admire the skyline of Chicago
Chicago Odyssey Lake Michigan dinner cruise
English
FromNZD 231.45
󱩳Wander through Millennium Park, State Street and The Loop
Festive Chicago food and walking tour
English
FromNZD 17.80
󱩳Exquisite flavors with consistently high quality
Restaurant Reservation Service for the Trendy Addison Restaurant in Chicago, USA
English
FromNZD 13.64
󱩳Exquisite flavors with consistently high quality
Reservation service for the popular Eleven Madison Park restaurant in Chicago, USA
English
FromNZD 13.64
󱩳Exquisite flavors with consistently high quality
Alinea, the popular restaurant in Chicago, USA - Restaurant Reservation Service
English
FromNZD 13.64
󱩳Enjoy panoramic skyline views from along the Chicago River
Architecture cruise on the Chicago River from Navy Pier
Duration: 75 mins
English
FromNZD 51.62
󱩳Enjoy delicious and sophisticated lakefront dining
Chicago Odyssey dinner cruise
English
FromNZD 348.33
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromNZD 53.44
󱩳Tease your taste buds and join this tour in the River North and Wicker Park neighborhoods
River North food tour
English
FromNZD 140.76
󱩳Get a taste of Chicago's most famous food in one of the city's most historic neighborhoods
Chicago ultimate food experience
Duration: 120 mins
English
FromNZD 133.63
󱩳Chinese-speaking driver at a fixed price (services available in Chinese and English)
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
FromNZD 166.31
󱩳Enjoy a buffet-style brunch with freshly prepared entrees, salads and desserts
Chicago Premier Lake Michigan brunch cruise
Duration: 120 mins
English
FromNZD 208.06
󱩳Taste your way through the Windy City's finger-licking food scene
Chicago favorites food walking tour
Duration: 180 mins
FromNZD 142.52
󱩳Explore Chicago's iconic architecture on foot,
Chicago in a Day: Food, History & Architecture Walking Tour
Duration: 4.5 hrs
4.8/5
Great· 24 reviews
5% off
Limited-time sale
FromNZD 167.72NZD 176.55
󱩳Enjoy a classic Chicago Italian Beef sandwich and original recipe brownie
Chicago: Classic Food and Walking Tour with Free Bike/Kayak
Duration: 3 hrs
5.0/5
Excellent· 5 reviews
5% off
Limited-time sale
FromNZD 135.51NZD 142.65