Semi-Private Sailboat Charters



2021 Semi-Private sailing season has ended.

Please click here for information about expired vouchers and extensions.


Semi-Private Sailboat Charters First-Class Sailing for 2 – $199

Wed and Sat Fireworks as well as other upgrades are frequently available.

Semi-Private Season: 5/15-9/15


 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.


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. We put small groups together to share our fantastic sailboats that are 36′-39′ long, and limit the group sizes to 6. 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.

<div “style=”clear:both” “=””>

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

Click here for information about expired vouchers.