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 25 weekday reservations and 11 weekend and holiday reservations where you will find one of our sailboats eagerly awaiting your arrival. During the workweek, take a load off and grab ahold of the helm (offered once a week) or sail away from all of your troubles and enjoy a four day adventure. This is not included in your 25 weekday and 11 weekend and holiday reservations.


With a wide range of sailing opportunities and an attractive seasonal fee, Captain’s Club’s value is hard to beat.

Captain’s Club includes our support to make your sailing days fun and easy.   From the moment you step on the dock, our professional staff will be there to help.   Our talented office, dock, and sailing staffs make your experience fun and enjoyable.

Captains Club Members Enjoy:

  • One-time seasonal fee. No initiation or membership charges.
  • 40+ reserved sailing dates per season
  • Weekday sailing with no reservation - once a week
  • Premium getaway days - 4 day trip
  • 15% Friends and Family discount for instructional courses
  • Active, vibrant social activities
32' Vessel
36' Vessel
40' Vessels

Call For Pricing

Call For Pricing

Call For Pricing

Call For Pricing

Terms and Conditions:

  • Each Captain's Club program requires a security deposit that is due upon signing of agreement.
  • Captain's Club Sessions:   0900-1500, 1500-2000 daily.
  • Weekday reservations need to be confirmed 48 hours prior to reserved time slot.
  • All vessels must be back 15 minutes prior to end of reservation so that the boat is clean and ready for the next customer.
  • Captain's Club reservations may be canceled due to weather concerns at the discretion of Chicago Sailing staff.
  • Chicago Sailing requires at least 2 people to be on board for all rentals. If you are a solo sailor, we can match you with other sailors through Skipper Connection.
Interested? Let chat.
Or Call Us: 773-871-SAIL x3



@chisail @chisail Like Us! 773-871-SAIL