ChicagoExperiences
ChicagoExperiences

Top Picks for Chicago Experiences

Discover 45 Experiences in Chicago on Trip.com, updated September 21, 2025, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From COP 54,173.16 per person, with an average total of COP 304,260.43. Choose the option that suits your plan.

With 83 verified reviews, Experiences Chicago boast an average rating of 4.9.

This week's most popular Experiences: "Bite into Chicago: Discover the City’s Most Iconic Food", with 81 reviews and a 4.7 rating.

Now on Trip.com: "Bite into Chicago: Discover the City’s Most Iconic Food", a 2-hour adventure in Chicago!

The next available day tour departs on September 22, 2025. Book now to secure your spot!

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

75% of Chicago Experiences now offer English-speaking guides

September is perfect for visiting Chicago! Choose from Experiences available day tours, including seasonal hits like Bite into Chicago: Discover the City’s Most Iconic Food.

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

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45 Results for Chicago Experiences

  • Chicago River 45-min architecture cruise
    󱩳Navigate all three branches of the Chicago River in a fully equipped vessel

    Chicago River 45-min architecture cruise

    Duration: 45–60 mins
    English
    FromCOP 54,173.16
  • Big Bus Chicago Hop-on Hop-off Bus Tour
    󱩳See the best of Chicago from the convenience and comfort of an open-top, double-decker bus. Hop on and hop off at any designated bus stop to explore major attractions at your own pace. Learn about the city's rich history from the informative commentary of a multilingual audio guide.

    Big Bus Chicago Hop-on Hop-off Bus Tour

    English
    5.0/5
    Excellent· 1 review· 34 booked
    FromCOP 139,899.90
  • Chicago Seadog: Lakefront Speedboat Tour

    Chicago Seadog: Lakefront Speedboat Tour

    Duration: 30 mins
    FromCOP 165,521.05
  • The Chicago Theatre Tour Experience

    The Chicago Theatre Tour Experience

    Duration: 1 hr
    English
    FromCOP 116,105.68
  • Skyline lake boat tour from Navy Pier
    󱩳Learn about Chicago's world-famous skyline cityscape and the history of Navy Pier

    Skyline lake boat tour from Navy Pier

    Duration: 45 mins
    English
    5.0/5
    Excellent· 1 review
    FromCOP 70,463.80
  • Spirit of Chicago dinner cruise
    󱩳Admire the skyline of Chicago

    Spirit of Chicago dinner cruise

    English
    FromCOP 451,842.79
  • Chicago Premier Lake Michigan brunch cruise
    󱩳Enjoy a buffet-style brunch with freshly prepared entrees, salads and desserts

    Chicago Premier Lake Michigan brunch cruise

    Duration: 120 mins
    English
    FromCOP 401,113.50
  • Bite into Chicago: Discover the City’s Most Iconic Food

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

    Duration: 2 hrs
    4.7/5
    Great· 81 reviews
    FromCOP 295,940.20
  • Chicago Odyssey dinner cruise
    󱩳Enjoy delicious and sophisticated lakefront dining

    Chicago Odyssey dinner cruise

    English
    FromCOP 756,489.38
  • Big Bus Chicago: Hop-on Hop-off Bus Tour

    Big Bus Chicago: Hop-on Hop-off Bus Tour

    Duration: 2 hrs
    English
    FromCOP 174,113.05
  • 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.

    All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States

    FromCOP 60,386.53
  • Chicago: Premier Dinner Cruise on Lake Michigan

    Chicago: Premier Dinner Cruise on Lake Michigan

    Duration: 150 mins
    FromCOP 682,268.58
  • Chicago: Food and Prohibition Architecture Guided Tour

    Chicago: Food and Prohibition Architecture Guided Tour

    Duration: 5 hrs
    English
    FromCOP 383,094.17
  • Chicago: Canine Cruise

    Chicago: Canine Cruise

    Duration: 90 mins
    English
    FromCOP 162,566.13
  • Lake Michigan: Premier Brunch or Lunch Cruise

    Lake Michigan: Premier Brunch or Lunch Cruise

    Duration: 2 hrs
    FromCOP 417,825.86
  • Chicago: Chinatown Food & Culture Walking Tour

    Chicago: Chinatown Food & Culture Walking Tour

    Duration: 3 hrs
    English
    FromCOP 309,539.37
  • Chicago: Guided Food Tasting + Bike Tour

    Chicago: Guided Food Tasting + Bike Tour

    Duration: 4 hrs
    English
    FromCOP 383,094.17
  • Chicago: Guided Food Tour + Bike or Kayak Rental

    Chicago: Guided Food Tour + Bike or Kayak Rental

    Duration: 150 mins
    English
    FromCOP 328,860.00
  • Chicago: Family & Food Guided Bike Tour

    Chicago: Family & Food Guided Bike Tour

    Duration: 4 hrs
    English
    FromCOP 309,539.37
  • Chicago: Food Tour + Bike or Kayak Rental

    Chicago: Food Tour + Bike or Kayak Rental

    Duration: 5 hrs
    English
    FromCOP 422,371.89
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