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ChicagoExperiences
ChicagoExperiences

Top Picks for Chicago Experiences

Discover 44 Experiences in Chicago on Trip.com, updated September 28, 2025, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From NZD 24.24 per person, with an average total of NZD 133.98. Choose the option that suits your plan.

With 396 verified reviews, Experiences Chicago boast an average rating of 4.9.

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

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

The next available day tour departs on September 29, 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

September is the perfect time to visit Chicago! Choose from Experiences available day tours, including seasonal favorites like Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More.

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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44 Results for Chicago Experiences

  • Chicago Architecture Sightseeing Cruise Experience [Departing from Michigan Avenue]|Depart from Navy Pier

    Chicago Architecture Sightseeing Cruise Experience [Departing from Michigan Avenue]|Depart from Navy Pier

    Duration: 1.5 hrs
    English
    FromNZD 84.39
  • The Chicago Theatre Tour Experience

    The Chicago Theatre Tour Experience

    Duration: 1 hr
    English
    FromNZD 51.94
  • Chicago: Food Tour + Bike or Kayak Rental

    Chicago: Food Tour + Bike or Kayak Rental

    Duration: 5 hrs
    English
    FromNZD 188.96
  • Skyline lake boat tour from Navy Pier

    Skyline lake boat tour from Navy Pier

    Duration: 45 mins
    English
    5.0/5
    Excellent· 1 review
    FromNZD 31.53
  • Chicago favorites food walking tour

    Chicago favorites food walking tour

    Duration: 180 mins
    FromNZD 138.47
  • Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More

    Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More

    Duration: 3 hrs
    4.9/5
    Excellent· 313 reviews
    FromNZD 154.06
  • Chicago: 90-Minute Architecture Tour on the Lake & River

    Chicago: 90-Minute Architecture Tour on the Lake & River

    Duration: 90 mins
    FromNZD 77.92
  • Architecture cruise on the Chicago River from Michigan Ave

    Architecture cruise on the Chicago River from Michigan Ave

    Duration: 75 mins
    English
    FromNZD 50.15
  • Chicago River 45-min architecture cruise

    Chicago River 45-min architecture cruise

    Duration: 45–60 mins
    English
    FromNZD 24.24
  • Chicago: Chinatown Food & Culture Walking Tour

    Chicago: Chinatown Food & Culture Walking Tour

    Duration: 3 hrs
    English
    FromNZD 138.49
  • Chicago Odyssey dinner cruise

    Chicago Odyssey dinner cruise

    English
    FromNZD 345.01
  • Big Bus Chicago Hop-on Hop-off Bus Tour

    Big Bus Chicago Hop-on Hop-off Bus Tour

    English
    5.0/5
    Excellent· 1 review· 34 booked
    FromNZD 62.69
  • Chicago Premier Lake Michigan brunch cruise

    Chicago Premier Lake Michigan brunch cruise

    Duration: 120 mins
    English
    FromNZD 179.44
  • Chicago Seadog: Lakefront Speedboat Tour

    Chicago Seadog: Lakefront Speedboat Tour

    Duration: 30 mins
    FromNZD 74.07
  • 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
    FromNZD 132.39
  • Chicago: Premier Dinner Cruise on Lake Michigan

    Chicago: Premier Dinner Cruise on Lake Michigan

    Duration: 150 mins
    FromNZD 305.23
  • Big Bus Chicago: Hop-on Hop-off Bus Tour

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

    Duration: 2 hrs
    English
    FromNZD 77.92
  • Chicago: Food and Prohibition Architecture Guided Tour

    Chicago: Food and Prohibition Architecture Guided Tour

    Duration: 5 hrs
    English
    FromNZD 171.39
  • Chicago: Canine Cruise

    Chicago: Canine Cruise

    Duration: 90 mins
    English
    FromNZD 72.71
  • Lake Michigan & Chicago River: 75 Minute Speedboat Cruise

    Lake Michigan & Chicago River: 75 Minute Speedboat Cruise

    Duration: 75 mins
    English
    FromNZD 234.27
  • Lake Michigan: Premier Brunch or Lunch Cruise

    Lake Michigan: Premier Brunch or Lunch Cruise

    Duration: 2 hrs
    FromNZD 163.29
  • Chicago: Guided Food Tasting + Bike Tour

    Chicago: Guided Food Tasting + Bike Tour

    Duration: 4 hrs
    English
    FromNZD 171.39
  • Chicago: Guided Food Tour + Bike or Kayak Rental

    Chicago: Guided Food Tour + Bike or Kayak Rental

    Duration: 150 mins
    English
    FromNZD 147.14
  • Chicago: Family & Food Guided Bike Tour

    Chicago: Family & Food Guided Bike Tour

    Duration: 4 hrs
    English
    FromNZD 138.49
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Reviews/Trip Moments

★
★
★
★
★
Reviews: Skyline lake boat tour from Navy Pier
Guest User2025-06-25
When booking on line and getting tickets emailed, information about which doc the boat is on would be great. We live out of state and had no idea which boat it was, where the doc is located we missed our time for departure. Luckily my tickets were honored for a later time.
★
★
★
★
★
Reviews: Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More
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.

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