Be Your Own Captain

Chicago Sailing is Chicago’s only public sailboat rental facility, providing a wide range of boats for you and your friends to enjoy. Rentals are available from morning til dusk, seven days a week, so you can enjoy sailing as often as you like. Take your friends sailing and show them the skyline!

We use J/22 and J/30 keelboats for their quality, design, and ease of handling. J/22s offer large, open cockpits and room for up to five adults. The J/30 is our entry level keelboat offering more space than the J/22s. Designed in the 1980s, the J/30 is a proven racer-cruiser that handles well in all conditions.  Our T-10 is one of Lake Michigan’s most popular racing vessels. It’s open, flat deck provides plenty of space for all of your passengers.

The Hunter-326s are cruising oriented with all imaginable conveniences for the discerning sailor. These boats offer additional creature comforts with ample seating, dry storage down below and a head onboard.

Imp & Bangarang, our two Beneteau yachts offer cruising comfort with speed and agility. At 36’, each yacht offers ample space and a lush interior for food and beverage staging as well as a comfortable refuge on hot days. The Oceanis 352 also offers a furling main for ease and comfort.

Our Catalina-400 is a cruising sailor’s dream boat with a huge cockpit, double wheels, and furling sails. The cockpit is large with lots of room to entertain friends. The interior boasts an enormous aft cabin with it’s own head and a spacious salon with forward head.

All of these vessels are available to skippers with appropriate sailing experience.

Your First Rental:

New renters are required to submit a sailing resume prior to their first rental. You can fill out our form online here, or email your current sailing resume to

Before your first rental, you will need to complete a checkout with our professional staff, in which you review the boat and our policies and safety procedures. Checkouts on our J/22s take place in the 15-20 minutes prior to your rental reservation. Checkouts on boats 30’ or larger can take an hour, and must be completed on a weekday. Once you have passed a checkout, you will be free to head out and enjoy the beauty of Lake Michigan. You may add a checkout to your cart while booking, or call the office to schedule your checkout.

Rental Policies

  • All rentals between 9am and 6pm have a 3 hour minimum
  • A 9% city tax is applied to all rental reservations
  • All rentals must be back 15 minutes prior to end of reservation so that the boat is clean and ready for the next customer.
  • All rentals must be back in the harbor before dusk.
  • Rentals may be canceled due to weather concerns at the discretion of Chicago Sailing.
  • Chicago Sailing requires at least 2 people to be on board all rentals.
  • All rental reservations are subject to Chicago Sailing’s 72-hour cancellation policy.

Rental Blocks

Rentals are broken into 4 daily blocks:
Block 1: 8:00am – 11:00pm (3hrs)
33% discount on all rentals during Block 1
Block 2: 11:00am – 2:00pm (3hrs)
Block 3: 2:00pm – 5:00pm (3hrs)
Block 4: 5:00pm – 8:00pm (3hrs)

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J/22 Rental Rates


Catalina 27

Catalina 27 Rental Rates

Weekday Rate: $90/hr
Weekend Rate: $105/hr
Capacity: 6
Quantity: 1
Size: 27′

Hunter 326

Hunter 326 Rental Rates

Weekday Rate: $145/hr
Weekend Rate: $165/hr
Capacity: 8
Quantity: 3
Size: 32′

J/30 & T-10

J/30 & T-10 Rental Rates

Weekday Rate: $105
Weekend Rate: $125
Capacity: 6
Quantity: 1 J/30 & 1 T-10
Size: 30′

Beneteau Oceanis 352

Beneteau Oceanis 352

Weekday Rate: $165/hr
Weekend Rate: $185/hr
Capacity: 10
Quantity: 1
Size: 36′

Catalina 400

Catalina 400 Rental Rates

Weekday Rate: $200/hr
Weekend Rate: $225/hr
Capacity: 10
Quantity: 1
Size: 40′