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?

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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 PHP 589.12 per person, with an average total of PHP 4,293.64. Choose the option that suits your plan.

With 432 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 perfect for visiting Chicago! Choose from Experiences available day tours, including seasonal hits 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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󱩳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
FromPHP 2,132.98
󱩳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
FromPHP 3,424.91
󱩳Global language translation allows you to communicate without worries no matter where you are, and start your health journey with peace of mind.
All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States
FromPHP 921.33
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromPHP 1,768.52
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
4.9/5
Excellent· 313 reviews
FromPHP 5,248.35
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 87 reviews
FromPHP 4,510.04
󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Chicago River 45-min architecture cruise
Duration: 45–60 mins
English
FromPHP 825.59
󱩳Enjoy panoramic skyline views from along the Chicago River
Architecture cruise on the Chicago River from Navy Pier
Duration: 75 mins
English
FromPHP 1,708.37
󱩳Taste your way through the Windy City's finger-licking food scene
Chicago favorites food walking tour
Duration: 180 mins
FromPHP 4,717.03
󱩳Enjoy a buffet-style brunch with freshly prepared entrees, salads and desserts
Chicago Premier Lake Michigan brunch cruise
Duration: 120 mins
English
FromPHP 6,885.95
󱩳Enjoy delicious and sophisticated lakefront dining
Chicago Odyssey dinner cruise
English
FromPHP 11,528.67
󱩳Tease your taste buds and join this tour in the River North and Wicker Park neighborhoods
River North food tour
English
FromPHP 4,658.65
󱩳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
FromPHP 4,422.77
󱩳Admire Chicago's amazing urban architecture from the Chicago River
Architecture cruise on the Chicago River from Michigan Ave
Duration: 75 mins
English
FromPHP 1,708.37
󱩳Wander through Millennium Park, State Street and The Loop
Festive Chicago food and walking tour
English
FromPHP 589.12
󱩳Admire the skyline of Chicago
Chicago Odyssey Lake Michigan dinner cruise
English
FromPHP 7,660.23
󱩳Immerse yourself in the world of motorcycles at the Harley-Davidson Museum
Chicago:Milwaukee City Highlights Day Trip with Brewery Tour
Duration: 8 hrs
English
FromPHP 7,371.27
󱩳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
FromPHP 5,497.52
󱩳Learn about the vibrant history of Chicago's Chinatown
Chicago: Taste of Chinatown Food Walking Tour
Duration: 2.5 hrs
4.8/5
Great· 21 reviews
5% off
FromPHP 4,754.84PHP 5,005.1
󱩳Explore the best hidden gourmet gems and off-the-beaten path spots
Chicago: River North Walking Food Tour
Duration: 3 hrs
5.0/5
Excellent· 1 review
5% off
FromPHP 5,538.23PHP 5,829.72