Best Boats & Yachts 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: Private Yacht Charter

Discover the magic of Chicago's waterways with a private yacht charter. Blend the thrill of the open lake with the iconic skyline of the city as a backdrop.

$1,820.00

~~From $2,275.00~~

Chicago River: 1.5-Hour Guided Architecture Riverboat Tour

45 Reviews

Chicago River: 1.5-Hour Guided Architecture Riverboat Tour

Climb aboard a unique 90-minute architecture riverboat tour of the famous Chicago River. Pass by over 50 significant Chicago buildings learning about their architecture and history via a live docent.

$49.00

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Chicago: Thanksgiving Gourmet Lunch Cruise on Chicago River

3 Reviews

Chicago: Thanksgiving Gourmet Lunch Cruise on Chicago River

Embark on a Premier Chicago Thanksgiving Lunch Cruise for an elegant afternoon celebrating on the Chicago River.

$136.54

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Chicago: Gourmet Brunch, Lunch, or Dinner River Cruise

70 Reviews

Chicago: Gourmet Brunch, Lunch, or Dinner River Cruise

Enjoy views of Chicago's riverfront architecture as you cruise along the Chicago River. Admire the scenery from the ship's glass-enclosed dining area. Choose between a lunch, dinner, or weekend brunch.

$110.57

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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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Chicago: Fireworks Gourmet Dinner Cruise on Lake Michigan

16 Reviews

Chicago: Fireworks Gourmet Dinner Cruise on Lake Michigan

Dine aboard our unique boat, the Odyssey, feasting on a gourmet three course meal served at your private table, then dance the night away to the live band and watch the beautiful fireworks over the Chicago skyline.

$153.94

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Chicago: Fireworks Cruise with Lake or River Viewing Options

248 Reviews

Chicago: Fireworks Cruise with Lake or River Viewing Options

Get up-close and personal to the epic Navy Pier fireworks display every Wednesday & Saturday during the Summer. Choose between viewing from either the Chicago River or Lake Michigan.

$28.00

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Best Seller

Chicago: 45-Minute Family-Friendly Architecture River Cruise

1146 Reviews

Chicago: 45-Minute Family-Friendly Architecture River Cruise

Cruise down the Chicago River and see the city’s most spectacular landmarks on a boat cruise with live, family-friendly commentary and a full-service bar on board.

$28.00

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Chicago: Wine & Cheese or Beer & BBQ Thursday Evening Cruise

11 Reviews

Chicago: Wine & Cheese or Beer & BBQ Thursday Evening Cruise

Enjoy a relaxing cruise on the Chicago River and Lake Michigan. Take in the skyline while enjoying a wine and cheese or a beer and BBQ tasting supplied by local purveyors.

$65.00

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Chicago River: Best 90-Min Architecture Boat Tour

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome.

$32.00

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Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour

33 Reviews

Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour

Climb aboard Windy, Chicago's official Tall Ship Ambassador, and experience breathtaking views from the water on this tall ship cruise. Sail along Lake Michigan and learn about Chicago's architecture.

$49.99

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Chicago: 75-Minute Architecture Cruise by Speedboat

361 Reviews

Chicago: 75-Minute Architecture Cruise by Speedboat

Enjoy Chicago's iconic skyline with an exciting speedboat tour departing from Navy Pier. View Chicago's unique architecture and famous landmarks from the water as you listen to the live narration.

$59.44

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