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Top Chicago Attractions & Tours

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Chicago Lakeside Architecture Tour

clock 1 hour 15 minutes
  • Leave the hustle and bustle behind, and enjoy a leisurely Skyline Sail aboard Chicago’s Official Tall Ship.

    Our crew today will be EXPLORING Chicago's architectural majesty while Windy sails across our beautiful lakefront skyline. To learn about the people, plans, and persistence that shaped Chicago's most famous sights, join us on the...Read more

Chicago Skyline Tall Ship Cruise

clock 1 hour 15 minutes
  • Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. This sail is approximately 75 minutes, with no guide...Read more

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

clock 2 hours
  • Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline.  Make the experience your own.  The flexibility of a private charter allows customization of virtually any aspect...Read more

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

clock 2 hours
  • Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline.  Make the experience your own.  The flexibility of a private charter allows customization of virtually any aspect...Read more
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