Schooner Windy - Private Chartrers

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Times shown are "cast-off" times. Please arrive 30-45 minutes early.

For all event descriptions


For specific sail, select the events name below.

Lakeside Architecture
Real Pirates
It's a Sailor's Life for Me!
Spirit Ships & Haunted Harbors
5:45p"Whale Watching" - Every Friday
Skyline Sail
Captain's Choice
9:15pm Wednesday Fireworks
9:15pm Saturday Fireworks

Sailing options:

Weddings and Wedding Parties

Field Trips


Educational Adventures


City of Chicago Resolution

Private Charters - Windy

Make your next gathering unique with a private cruise on a real tall ship!

Set sail on Windy for weddings, parties, corporate functions, reunions, church outings, tour groups, team building, and more! Windy can be chartered for a maximum of 150 guests.


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!


Prices start at $2,400 (taxes included) for your private event.

For a basic rates schedule, click here


Caterers generally set up buffet-style in the grand salon, adjacent to the galley area, with guests free to move in and out. Seating is informal on the Windy, so "picnic-style" meals work best. Our preferred caterers include:


Private charters include the option of a docent aboard for historical interpretation and Windy's exciting signature programming. Choose from Lakeside Architecture, Piracy on the Great Lakes, maritime ghost stories, and more.

Live music is also available.

Contact us at 312.451.2700 to have a quote sent to you, and to schedule your cruise!