Chicago Sailing

Skyline Sail - May to Sept
★ 4.6 (435) • $35-64 Person • 75 Minutes • 148 Passenger Max (all ages) • Pirate, Architecture, Happy Hour, Sunset Options
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Educational Sail: Tall Ship Discovery Sail
★ 4.6 (435) • $25-35 Person • 90 Minutes • 148 Passenger Max (all ages) • Educational Sail
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Skyline Sail - May to Oct 1

AVAILABLE NOW SAIL DAILY MAY THROUGH OCTOBER 1!
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.

  • 1pm Daily: Pirates and Maritime Stories

  • 3pm Daily: Architecture and Skyline Sail

  • 5pm Daily: Enjoy Happy Hour Specials during the Sunset and Skyline Sail

    7pm Daily: Late Summer Twilight Sail
    -- 7pm Thursdays: Special Pirate Storytelling Sail

Educational Sail: Tall Ship Discovery Sail

SHARE THE MARVEL of maritime heritage on the Great Lakes! History comes alive with an exciting educational adventure for curious minds of all ages. Join a local school or youth group, on their sail training mission, for hands-on sailing aboard Windy, and then muster for learning stations led by our crew-educators. This is approximately a 90 Minute sail.

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