Skip to primary navigation Skip to content Skip to footer
  • Most Popular!

Chicago Skyline Sail

Quick Details

Standard Boarding
Adult Ages 13+
Child Ages 2-12
Infant Ages 0-1
VIP Captains Boarding
Adult Ages 13+
Child Ages 0-12

Experience The Beautiful Chicago Lakefront With Three Sailing Options

Tall Ship Windy offers three exciting ways to enjoy the Chicago lakefront and skyline. Scroll down to learn more about our Skyline sails and book today!

Skyline Sail

Experience Breathtaking Views of Chicago from the Water! Leave the hustle and bustle behind and explore Chicago’s gorgeous 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. There’s no better place from which to watch the sun as it sets over our beautiful city. Don’t miss this scenic cruise from a traditional tall ship!

Architecture Sail

Head out on our traditional tall ship and explore 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 main deck and enjoy the lively and educational narration. From our historical maritime roots to modern science and technology, prepare to be delighted with interesting facts, unique stories, and a healthy dose of whimsy.

Tales of Real Pirates

Join us on our main deck for “True Stories of Piracy” on the Great Lakes! From epic battles to trickery and treasure, experience the incredible tales of real pirate adventure that happened right here on these magnificent inland seas. This Chicago sail is both educational and entertaining!

On this unforgettable sail, you also get to enjoy awe-inspiring views of the world-famous skyline of the Windy City while sailing the gentle waters of Lake Michigan. There’s something for everyone in the family on this fun tour.

Private Charters

Please visit our private charters page for more info or download our charters fact sheet here.

Skip to toolbar