Welcome to Windy City Sailing, Chicago Sailing Charters

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


3 Responses to Welcome to Windy City Sailing, Chicago Sailing Charters

  1. Dee Harrison says:

    We went out yesterday for a three hour charter and had a fantastic time! The weather for FANTASTIC (for Chicago) and the yacht and captain from Windy City Sailing could not have been better! A+ with FOUR STARS! Will go again soon
    – Dee

  2. Elizabeth says:

    We took the family out with Windy City Sailing for an afternoon on the water to celebrate Grandma’s birthday. She was very nervous starting out but the whole trip was fantastic. The crew was hospitable, personable, and very knowledgeable. They took great care of us and we felt safe the whole time. The boat was amazing and the facilities fantastic. The grandkids are still talking about how much fun they had hanging out on the boat and grandma is ready to go back out again soon. Thank you.

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