Value and Semi-Private Sailboat Charters



2023: Semi-Private 6-person voucher makeup sails.

Please click here for information about expired vouchers and extensions.

Morning Sails
Sat/Sun- 9am (times may vary)

Sunset Sails

Mon/Tue/Thu : 6:30pm or 7:00pm (times may vary)



First-Class sailing

One of our beautiful sailboats.


As of July 14, 2022, there will be no availability for 2-person vouchers and only 6-person reservations will be offered. Please click here for details.

Chicago Sailboat Charters offers Semi-Private sails so that groups of 2 or 4 can share a First-Class sailboat on an economy class budget. Sail on our fantastic sailboats that are 36′-39′ long. These boats can very comfortably hold 6 people, so you know you will be cruising in comfort and style.
All Semi-Private sails are 2 hours (fireworks upgrades are 3 hours), and take place Saturday, Sunday, and many Holiday Mornings, as well as Monday, Tuesday, Thursday evenings. Some other sailings, such as weekend afternoons and evenings, Friday nights, and Wednesday and Saturday fireworks, are offered for an upgrade fee when possible.

Children must be at least 12 years old to sail on semi-private sails (unless you are a group of 6 – which means only your group is on the boat, in which case you must have at least 1 adult per child under 12 in your group). Seats are only sold in multiples of 2.

Semi-Private sails may not be offered around July 4th and Air Show weekend.

Click here for information about expired vouchers.