Book Now  Specials
"BIG BOAT" - up to 36 people
REWARDS         Pricing / Availability

Rewards Program

Yes, boating rewards! Earn 10% credit on future charters for the same or larger class of boat. No blackout dates or times, and you already earned rewards with your 2022 private charters. Rewards Program

Chicago Sailboat Charters (it’s more than a name)

We must be doing something right… If you search “Chicago Sailboat Charters”, all the second and third rate charter operations out there have paid for ADs that put our name in some kind of awkward sentence somewhere in their text. So they are PAYING to show THEIR AD with OUR NAME, hoping that people carelessly […]