Tall Ship Windy, Chicago

About Tall Ship Windy

Tall Ship Windy is a 148-foot, four-masted schooner offering public sailing tours and special event cruises from Navy Pier in Chicago. Visitors board the vessel for Chicago Skyline Sails lasting approximately two and a half hours, viewing the city's lakefront. The ship also hosts Navy Pier Fireworks Cruises for evening viewing of the fireworks display, as well as specialty sails featuring live blues music during the Monday Night Concert Series and experiences during the Chicago Air and Water Show. The schooner's deck offers multiple vantage points for observing the skyline and waterfront. Group outings and private charters are available for occasions like weddings. Season pass memberships grant access to eligible Skyline Sails throughout the sailing season, with options for weekday-only or full-week access and priority boarding on select tiers. Tickets are sold online on the venue's site.