Private Sailing Yacht Charters on the Chicago Lakefront

Windy City Sailing provides World-Class recreational, romantic and educational experiences to individuals and small groups. Experience the thrill of sailing, with United States Coast Guard certified captains on our custom sailing yachts.

~Windy City Sailing Provides the Following Services~

Private Sailboat Charters for 1 – 6 Passengers

Bed and Breakfast Service on Luxury Sailing Yachts

Private Firework Charters at Navy Pier

Special Events on Chicago’s Lakefront- Jazz Fest, Blues Fest and Taste of Chicago

July 4th Fireworks – Chicago Air & Water Show

Celebrations and Once-in-a-Lifetime Events

Specializing in Proposals

Gift Certificates for All Events

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