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Top Picks for Chicago Tours

Discover 99 Tours in Chicago on Trip.com, updated September 18, 2025, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From GBP 7.32 per person, with an average total of GBP 58.80. Choose the option that suits your plan.

With 5.529k verified reviews, Tours Chicago boast an average rating of 4.8.

This week's most popular Tours: "Chicago Favorites Ultimate Food and Walking Tour ", with 1.753k reviews and a 4.8 rating.

Now on Trip.com: "1-day tour of Chicago, USA", a 5-hour adventure in Chicago!

The next available day tour departs on September 19, 2025. Book now to secure your spot!

Chicago Tours usually take about 5 hours — perfect for a relaxed, immersive experience!

75% of Chicago Tours now offer English-speaking guides

September is the perfect time to visit Chicago! Choose from Tours available day tours, including seasonal favorites like Chicago Favorites Ultimate Food and Walking Tour .

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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99 Results for Chicago Tours

  • 1-day tour of Chicago, USA

    1-day tour of Chicago, USA

    Duration: 5.7 hrs
    English
    4.5/5
    Satisfactory· 4 reviews
    From£106.63
  • Chicago architectural sightseeing cruise (departing from Michigan Avenue or Navy Pier) 83929

    Chicago architectural sightseeing cruise (departing from Michigan Avenue or Navy Pier) 83929

    Duration: 1 hr
    English
    From£36.81
  • Lake Michigan Skyline Cruise in Chicago

    Lake Michigan Skyline Cruise in Chicago

    Duration: 45 mins
    4.5/5
    Satisfactory· 246 reviews
    From£24.00
  • Chicago Loop: Art, Skyscrapers, Millennium Park & "The Bean"

    Chicago Loop: Art, Skyscrapers, Millennium Park & "The Bean"

    Duration: 2 hrs
    5.0/5
    Excellent· 6 reviews
    From£36.30
  • Hidden In Plain Sight: Chicago Prohibition Tour

    Hidden In Plain Sight: Chicago Prohibition Tour

    Duration: 210 mins
    English
    From£33.34
  • Chicago: Guided Food Tour + Bike or Kayak Rental

    Chicago: Guided Food Tour + Bike or Kayak Rental

    Duration: 150 mins
    English
    From£62.96
  • Chicago Favorites Ultimate Food and Walking Tour

    Chicago Favorites Ultimate Food and Walking Tour

    Duration: 3 hrs
    4.8/5
    Great· 1.8k reviews
    From£62.74
  • Chicago in a Day: Explore Food, History, and Iconic Architecture

    Chicago in a Day: Explore Food, History, and Iconic Architecture

    Duration: 5 hrs
    4.9/5
    Excellent· 1.1k reviews
    From£74.52
  • Art Institute of Chicago Private Expert Guided Tour

    Art Institute of Chicago Private Expert Guided Tour

    Duration: 2 hrs
    From£291.58
  • Chicago City Minibus Tour

    Chicago City Minibus Tour

    Duration: 2 hrs
    4.9/5
    Excellent· 298 reviews
    From£35.40
  • Chicago Crime and Mob Bus Tour

    Chicago Crime and Mob Bus Tour

    Duration: 90–120 mins
    4.7/5
    Great· 1.4k reviews
    From£36.18
  • Chicago City Tour with Architecture River Cruise Option

    Chicago City Tour with Architecture River Cruise Option

    Duration: 2–4 hrs
    4.8/5
    Great· 655 reviews
    From£36.14
  • Explore Chicago’s Hidden Past: Prohibition Culture & Architecture

    Explore Chicago’s Hidden Past: Prohibition Culture & Architecture

    Duration: 150 mins
    4.8/5
    Great· 89 reviews
    From£36.88
  • Chicago: Food Tour + Bike or Kayak Rental

    Chicago: Food Tour + Bike or Kayak Rental

    Duration: 5 hrs
    English
    From£80.86
  • Chicago Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters

    Chicago Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters

    Duration: 2 hrs
    English
    From£36.28
  • Chicago Night Crimes Bus Tour: Criminals, Mobsters and Gangsters

    Chicago Night Crimes Bus Tour: Criminals, Mobsters and Gangsters

    Duration: 150 mins
    English
    From£40.72
  • Chicago: Craft Brewery Barrel Bus Tour

    Chicago: Craft Brewery Barrel Bus Tour

    Duration: 225 mins
    English
    From£73.79
  • Chicago: Food and Prohibition Architecture Guided Tour

    Chicago: Food and Prohibition Architecture Guided Tour

    Duration: 5 hrs
    English
    From£73.34
  • Chicago: Highlights & Attractions Walking Tour

    Chicago: Highlights & Attractions Walking Tour

    Duration: 2 hrs
    English
    From£36.75
  • Chicago: Chinatown Food & Culture Walking Tour

    Chicago: Chinatown Food & Culture Walking Tour

    Duration: 3 hrs
    English
    From£59.26
  • Chicago: Downtown TV and Film Walking Tour

    Chicago: Downtown TV and Film Walking Tour

    Duration: 2 hrs
    English
    From£29.64
  • Chicago: Signature Dishes Bike Tour

    Chicago: Signature Dishes Bike Tour

    Duration: 4 hrs
    English
    From£66.67
  • Chicago: 48-Hour Hop-on Hop-off Bus + Architecture Cruise

    Chicago: 48-Hour Hop-on Hop-off Bus + Architecture Cruise

    English
    From£73.34
  • Original Chicago Prohibition Tour

    Original Chicago Prohibition Tour

    Duration: 4 hrs
    English
    From£40.75
  • Chicago: Guided Highlights Tour + SkyDeck + Architecture Cruise

    Chicago: Guided Highlights Tour + SkyDeck + Architecture Cruise

    Duration: 4 hrs
    English
    From£95.51
  • Scenic Chicago Night Tour

    Scenic Chicago Night Tour

    Duration: 210 mins
    English
    From£125.12
  • Chicago: Culture & Architecture Guided Tour

    Chicago: Culture & Architecture Guided Tour

    Duration: 150 mins
    English
    From£36.31
  • Chicago Bus Tour: 90-Min Sunset Tour

    Chicago Bus Tour: 90-Min Sunset Tour

    Duration: 90 mins
    English
    From£36.07
  • Signature dishes of Chicago bike tour

    Signature dishes of Chicago bike tour

    English
    From£65.87
  • Chicago lakefront neighbourhood bike tour

    Chicago lakefront neighbourhood bike tour

    English
    From£7.32
  • Chicago: Creepy Cruise

    Chicago: Creepy Cruise

    English
    From£30.91
  • Ultimate city bike tour in Chicago

    Ultimate city bike tour in Chicago

    English
    From£8.05
  • Chicago: Guided Haunted Tour

    Chicago: Guided Haunted Tour

    Duration: 1 hr
    English
    From£19.14
  • Chicago Pizza Bus Tour Ticket

    Chicago Pizza Bus Tour Ticket

    Duration: 210 mins
    English
    From£65.11
  • Chicago Downtown: 3-Hr Guided Pizza Tour

    Chicago Downtown: 3-Hr Guided Pizza Tour

    Duration: 3 hrs
    English
    From£50.48
  • Chicago Film and Television Tour: Skyscraper Fantasy Light and one-day tour

    Chicago Film and Television Tour: Skyscraper Fantasy Light and one-day tour

    Duration: 3 hrs
    English
    From£91.90
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