Captained Charters

Sit back and relax while one of out USCG licensed captains shows you and your guests the ropes, and the skyline.

Sit Back and Enjoy The Ride

​Would you like to get away from it all for a few hours? What about a charter sailing adventure on the lake with a professional captain as your sailing master and host? At Chicago Sailing we provide you and your guests with the opportunity to enjoy a personal holiday. You choose the route of your adventure and your professional captain will make your sailing dreams come true. Sailing offers a creative alternative for everything from a family reunion to entertaining important clients, all in a casual, outdoor setting. Sailing is easy for everyone to enjoy, regardless of his or her sailing experience. It is a great way to involve all members of your group in an activity that requires no level of proficiency.

Choose Your Perfect Vessel

With over 20 vessels ranging from 22′-53′, we have the perfect boat for your outing.

Due to USCG regulations a standard charter can have no more than 6 passengers, if your group is larger than 6 we can still accomodate you through a bareboat charter. Click below to find out more.

More Than 6 Passengers?

Hunter 326

Weekday Rate: $175/hour
Weekend Rate: $200/hour
Capacity: 6*
Available for larger groups as a bareboat charter*

IMP

Weekday Rate: $195/hour
Weekend Rate: $230/hour
Capacity: 6*
*Available for larger groups as a bareboat charter

Bangarang

Weekday Rate: $195/hour
Weekend Rate: $230/hour
Capacity: 6*
*Available for larger groups as a bareboat charter

Alize

Weekday Rate: $230/hour
Weekend Rate: $265/hour
Capacity: 6*
*Available for larger groups as a bareboat charter

Bumblebee

Weekday Rate: $245/hour
Weekend Rate: $275/hour
Capacity: 6*
*Available for larger groups as a bareboat charter

Contact Us

Questions about our Charters? Fire away! We are here to get you and your guests out on the water.


Dock B, 2 W Belmont Harbor Dr, Chicago IL 60657
contactus@chicagosailing.com
773-871-7245

Say Hello!