Top Illinois Sailing
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3 results | All Illinois Tours
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Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side.
…More
From
$427.28
per group
From
$427.28
per group
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.
…More
From
$427.28
per group
From
$427.28
per group
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Real Pirates of the Inland Seas: Chicago Pirate-Themed Sailboat Tour
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.
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From
$40.46
From
$40.46
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