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Top Chicago Sailing Trips

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

Chicago Lakeside Architecture Tour

Get views of Chicago's famous architecture from the deck of a boat during this sailing excursion. Learn about the people, plans, and persistence that shaped Chicago's architecture along the shoreline. Hear about the city's historical maritime roots to modern science and technology through your guide's commentary while taking advantage of great photo ops. Choose between an afternoon or early evening departure and relax as you enjoy the sights. 
  • Duration: 1 hour 15 minutes
  • Duration: 1 hour 15 minutes
From  
$37.00
From  
$37.00
See Details

Real Pirates of the Inland Seas Sail

Experience Lake Michigan from a perspective rare to visitors and locals alike on a pirate–themed sailboat tour. Your guides tell true but little–known stories about pirates, battles, and treasure hunts as you cruise past sweeping views of the Chicago skyline. Relax on deck while or join your guides for an interactive experience—the flexibility of the tour makes this a popular choice for families with children.
  • Duration: 1 hour 15 minutes
  • Free Cancellation
  • Duration: 1 hour 15 minutes
  • Free Cancellation
From  
$37.00
From  
$37.00
See Details

Chicago Skyline Sightseeing Cruise

Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs.
  • Duration: 1 hour 15 minutes
  • Free Cancellation
  • Duration: 1 hour 15 minutes
  • Free Cancellation
From  
$33.60
From  
$33.60
See Details


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