Quick Details
Experience breathtaking views of Chicago from the waters of Lake Michigan! Leave the hustle and bustle behind and explore Chicago’s gorgeous shores and skyline with a leisurely trip around Lake Michigan.
There’s no better place to view Chicago or Lake Michigan than aboard 148′ S/V Windy; the Official Tall Ship Ambassador for the City of Chicago. Don’t miss these scenic and educational cruises from Chicago’s famous traditional tall ship! Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tours at 3pm and 5pm and Sunset and Skyline Sails at 7pm.
Experience The Beautiful Chicago Lakefront With Three Sailing Options
Tall Ship Windy offers three exciting ways to enjoy the Chicago lakefront and skyline. Learn more about our Skyline sails and book today!
1pm. Pirates and Maritime Stories
Join us on our main deck for “True Stories of Piracy” on the Great Lakes and the Caribbean! 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 will also 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 on this fun tour.
3pm & 5pm. Architecture and Skyline Sails
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. The 3pm and 5pm tours feature the history of Chicago and its world-famous architecture. 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.
5PM: Happy Arr-our Chicago Skyline Sail
Enjoy onboard happy hour drink specials every night at 5pm! All ages welcome. Happy hour specials for guests 21+, with valid ID.
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Our sailing schedule changes with the season. Beginning September 3, enjoy a Sunset Skyline sail at 5pm and a Late Summer Twilight Sail at 7pm.
7pm. Sunset and Skyline Sail
Head out on our traditional tall ship and explore the majesty of Lake Michigan while Windy sails across our beautiful lakefront Chicago skyline. From the world-famous Tall Ship Windy, experience the phenomenal sun setting across the Chicago Skyline. A perfect Sunset Skyline Sail for individuals, family and friends.
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Our sailing schedule changes with the season. Beginning September 3, enjoy a Sunset Skyline sail at 5pm and a Late Summer Twilight Sail at 7pm.
On our Twilight Sail, enjoy the beautiful colors splashed across the post-sunset sky. You’ll enjoy an evening sail on Lake Michigan aboard Tall Ship Windy and take in the world-famous Chicago skyline as day transitions to night.
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All seating on board Tall Ship Windy is first come, first served. Guests with VIP Captains Boarding tickets board first before General Admission ticket holders. A limited number of VIP tickets are available and are likely to sell out. Board first to choose your seat on one of Windy’s three decks: the forward, middle or aft.
All VIP Captains Boarding tickets also include trip insurance. Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.
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$8.00 Per Guest | Add to your ticket at checkout
Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. Refunds for cancelled charters are less the $8.00 cost of insurance and 3% booking fees.
General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.
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- RAIN OR SHINE EVENT: In the unlikely event that your tour is cancelled, you may exchange your ticket for another day or receive a refund.
- No-shows will not be eligible for rescheduling or refund. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture.
- The Captain reserves the right to postpone a sail for up to 15 minutes in the case of passing inclement weather.
- General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.
- Add-on Trip Insurance: Allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time.