Group Sales and Discounts Aboard the Windy!

Group Discounts

Make your next group outing unique with a real tall ship sailing adventure! Tall Ship Windy is a majestic 148-foot, four-masted gaff topsail schooner. Modeled after a traditional Great Lakes trading ship, she is built of modern materials but boasts all the character and charm of the Golden Age of Sail.

Bring your family trip, reunion, retreat, happy hour, or celebration to one of Windy’s regular sails! Whether you’re looking for hands-on adventure, intriguing history, or a leisurely cruise, Windy has something for you!

Download small group sales fact sheet: Small group sales inquiry

Download private charter fact sheet: Windy charter inquiry document


20-39 group size: 10% discount

40-59 group size: 15% discount

60 or more: 20% discount

Private Charters

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


Contact us at 312-451-2700 for private charter pricing, scheduling, and more information.


Windy boasts three spacious decks, a grand salon, pressurized “heads” (marine toilets), and a bar for your enjoyment. Plenty of deck seating is available on benches and boxes. The bar is stocked with soda, water, beer, wine, liquor, and snacks. Ask about our bar packages! We feature brands from local distilleries and wineries.


Windy’s signature programming combines exciting Great Lakes history with interactive storytelling for curious minds of all ages. Our knowledgeable docents bring the history to life, so you can experience Chicago like never before!

On Windy, explore Chicago architecture, piracy on the Great Lakes, Chicago, and more. Navigate the site to see our daily sailing schedule and to find a program that fits your group!

Cancellation Policy:

No refunds, no exchanges without the purchase of additional trip insurance: Rain or shine event. 

No-shows will be charged the full price. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture.

All sales are final. The captain reserves the right to postpone a sail for up to 120 minutes; if the sail is canceled, tickets may be exchanged for another time.

No refunds, no exchanges without the purchase of additional trip insurance. Sailing on the Windy is a Rain or shine event.