How Much Does it Cost to Have a Boat in Chicago?

Chicago and the Great Lakes offer cruising and racing grounds for all levels and budgets. Learn the cost specifics for a region with proper winters, robust regatta offerings and a buzzing yacht club scene.

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A Sabre 38 Mk I on a classic Chicago windy day in early June. One reef in the main and a fully furled genoa kept her balanced. (Photo/ Nick Van Antwerp)
A Sabre 38 Mk I on a classic Chicago windy day in early June. One reef in the main and a fully furled genoa kept her balanced. (Photo/ Nick Van Antwerp)

Sailing is a weather dependent sport. When I learned to sail, I would head out on Lake Michigan in heavy wind, light wind, rough seas and calm seas—the best conditions always seemed to elude the confines of class. The same is true for regattas and other large trips planed well in advanced. I worked in an office where I could see a sliver of the lake from our office conference room. I’d look out to see if there were ideal conditions—10 to 12 knots and calm seas. During this time, I had access to my yacht club’s fleet of keel boats so I’d look at the reservations for the fleet only to see, unfortunately, that all boats would be in use.

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Nick Van Antwerp
Nicholas is a licensed architect in Montana, where he works primarily on custom single-family homes and ranches. He grew up in the Midwest where he fell in love with sailing at a young age, learning from his dad on the family’s Hobie 16. He participated in a local sailing school where he learned to race in dinghies. He applied his knowledge to one design racing, sailing in the Farr 40, Melges 24 and J 70 classes. Outside of buoy racing, he has competed in offshore races such as a Chicago to Mackinac, Caribbean 600 and has completed a trans-Atlantic delivery. In addition to his personal sailing, Nick has been an instructor for adult keel boat classes and youth learn-to-sail and racing programs.