Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail.
- 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!
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!
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.
- VIP boarding
- Trip insurance
These optional items are available for purchase when you book:
- Windy Drink Tickets: 20% off a full price drink. $10 value redeemable for drinks only. No cash value.
- Trip Insurance: $3.50 per person—gives you the ability to cancel your reservation and receive a full refund. This applies if you need to cancel up to 24 hours before your scheduled sail time or if Tall Ship Windy cancels your sail due to weather.
- No-shows will be charged the full price. Guests must arrive at least 45 minutes before the scheduled departure time or risk forfeiture.
- The captain reserves the right to postpone the sail for up to 120 minutes; if the sail is cancelled, tickets may be exchanged for another time.
- All sales are final.
- No refunds and no exchanges are available without the purchase of additional Trip Insurance. The Windy sails rain or shine.