Sail More, Pay Less


For those who are looking to make the most of their season of sailing, without breaking the bank we offer several seasonal sailing options.  Our programs offer a variety of options that meet your specific sailing and financial needs, save up to 80% over our traditional rental rates, with guaranteed boat availability.

Not Just Another Fractional Program

There are many fractional sailing providers out there, but Chicago Sailing prides itself on being a cut above the rest.  With our own commercial dock and full time on site staff there is always a team of people there to help you get out on the water.  Our maintenance team ensures that your boat is always clean and ready to go before your arrival, which means you never have to hassle with cleaning up, fueling, or pumping out.  Having catering delivered? No problem! Have your catering company drop off your food and beverage in our office and it will be placed on the boat before your arrival.

Sail’s Call

Ditch dryland and set sail all season long with our seasonal ownership program, Sail’s Call. Members enjoy 3 weekday sails for either a full season or half season, all for one low time fee.

Just walk down the dock and pick any available vessel in our fleet for up to three hours; No need for a reservation! Sails Call also includes free checkouts on all our sailboats from 22’ all the way up to the 40’. Share your passion for the water with our 15% friends and family discount on all instructional courses. Let us put the wind in your sails; breeze into Sails Call and start saving today.

Captain’s Club

Let the lake steal your breath away all season long without spending a fortune. Join our fractional ownership program, the Captain’s Club, and enjoy smooth sailing- from the docks to open water.

This is the perfect package if you are craving more time on the water. For a single seasonal payment, climb aboard for 35 weekday reservations and 15 weekend and holiday reservations where you will find one of our sailboats eagerly awaiting your arrival. You can even sail away from all of your troubles and enjoy a four day adventure.