Best Cruises & boat tours in Chicago

Local Recommendations from our My Guide Chicago team

Book Top Experiences and Tours in Chicago:

If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!

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Chicago District: A Self-Guided Audio Tour

1 Reviews

Chicago District: A Self-Guided Audio Tour

Breeze through the captivating art and architecture in the iconic Windy City on this self-guided audio tour. Experience the magic of GPS-playback on this immersive stroll through Chicago.

$11.99

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Chicago: Architecture Boat Tour with Drinks

73 Reviews

Chicago: Architecture Boat Tour with Drinks

Experience the iconic scenery, skyscrapers, and architecture of Chicago on a guided boat cruise through the heart of the city. Pass by the Willis Tower, Wrigley Building, Tribune Tower, and more.

$35.00

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Chicago: 1.5-Hour Lake and River Architecture Cruise

1380 Reviews

Chicago: 1.5-Hour Lake and River Architecture Cruise

Skip the ticket line for Chicago’s only architecture cruise on both Lake Michigan and the Chicago River. Learn about Chicago's internationally-known architecture from expert local guides as you discover the city from riverfront to shoreline.

$44.00

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Chicago River Architecture and History by Private Boat Tour

Discover Chicago by private boat with a local Chicagoan to highlight its fascinating history and architectural marvels along the way!

$695.00

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Walkin' with Colin: Chicago Tour du Jour

1 Reviews

Walkin' with Colin: Chicago Tour du Jour

Walkin'W/Colin is a one of a kind feet on the street experience recommended by 100% of travelers on Trip Advisor! Chicago History-Mystery-Comedy-Tragedy on a tour du jour in the heart of the city!

$29.48

~~From $44.00~~

Chicago eSIM: Instant Activation USA 4G/5GB

Experience seamless connectivity throughout USA with our eSIM, and enjoy savings of up to 90% on roaming charges. Enjoy a hassle-free mobile data plan with the flexibility to top up as needed.

$3.20

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Chicago: Architecture River Cruise Skip-the-Ticket Line

3880 Reviews

Chicago: Architecture River Cruise Skip-the-Ticket Line

Cruise along the Chicago River on a boat tour and discover hidden architectural gems among the city’s renowned landmarks, with live narration.

$53.00

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Best Seller

Chicago: Taste of Chinatown Food Walking Tour

58 Reviews

Chicago: Taste of Chinatown Food Walking Tour

Discover the delicious, multiregional cuisine on this wonderful Chinatown Food & Culture Tour. Expand your culinary horizons with unique dishes while learning about the fascinating Chinese culture.

$79.99

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Discovering Chicago with Walking In App Audio Tour

Join In App Audio tour in Chicago and imagine yourself being on a film set

$6.00

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Chicago River: Guided Sunset Cocktail & Architecture Tour

52 Reviews

Chicago River: Guided Sunset Cocktail & Architecture Tour

Climb aboard a 90 passenger historic riverboat & sip cocktails while cruising the Chicago River! Relax and learn about the history & architecture of the city via live narration with a drink in hand.

$59.00

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Chicago: Lake Michigan Educational 'Tall Ship Windy' Cruise

8 Reviews

Chicago: Lake Michigan Educational 'Tall Ship Windy' Cruise

Take an exciting educational adventure aboard Tall Ship Windy with this cruise from Navy Pier in Chicago. Watch as Great Lakes history and maritime traditions come to life.

$29.00

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Chicago: City Minibus Tour with Optional Architecture Cruise

108 Reviews

Chicago: City Minibus Tour with Optional Architecture Cruise

Discover downtown Chicago, as well as some nearby neighborhoods on a minibus tour. Choose to add an architectural cruise of Chicago for the best way to see Chicago from both land and water.

$47.95

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