Private Sailing Yacht Charters on the Chicago Lakefront
Windy City Sailing provides World-Class Chicago sailboat rental for recreational, romantic and educational experiences to individuals and small groups. Experience the thrill of sailing and Chicago sightseeing with United States Coast Guard certified captains on our custom sailing yachts.
Windy City Sailing Provides the Following Services on Lake Michigan:
- Private Sailboat Charters for 1 – 6 Passengers, our lakefront is the number one “Chicago tourist attraction”
- Bed and Breakfast Service on Luxury Sailing Yachts, romantic accommodations paired with sailing in Chicago!
- Private Firework Charters at Navy Pier, go sailing off the beaten path and end the day with a spectacular overhead fireworks display.
- Special Events on Chicago’s Lakefront- Jazz Fest, Blues Fest and Taste of Chicago, rent a yacht and arrive in style!
- July 4th Fireworks – Chicago Air & Water Show both are major Chicago attractions best enjoyed on a Lake Michigan cruise!
- Celebrations and Once-in-a-Lifetime Events, birthdays, anniversaries, proposals, family reunions, and other very special occasions .
Specializing in Proposals | Gift Certificates for All Events