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Windy City Sailing, Chicago

#4 of 10 in Transportation in Chicago
Boat Rental · Boat Tour
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


- July 4th Fireworks - Chicago Air & Water Show

- Celebrations and Once-in-a-Lifetime Events

- Specializing in Proposals

- Gift Certificates for All Events
For travelers who use our custom trip planner, Chicago holidays become easier to arrange, with trips to the Windy City Sailing and other attractions mapped out and timetabled.
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Windy City Sailing reviews

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TripAdvisor traveler rating 5.0
52 reviews
  • Windy City Sailing always exceeds expectations. My family and I look forward to our annual sailing trip w/ Captain Joe and his crew. Even just unplugging on a three hour tour beats some week long...  more »
  • We had such a great time with Captain Marty and his first mate. We had two kids with us, and they made it so much fun for them while keeping everyone safe. They both taught the kids a lot about...  more »

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