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′ including a selection of power boats and sailboats, we have the perfect boat for your outing.

Looking for catering options? No problem, we work with several local catering companies and can provide you with “boat friendly” menu options.

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?

J/22

Weekday Rate: $100/hour
Weekend Rate: $125/hour
Capacity: 4

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

Naida

Weekday Rate: $450/hour
Weekend Rate: $500/hour
Capacity: 6*
*Available for larger groups as a bareboat charter

J/30 & T-10

Weekday Rate: $140/hour
Weekend Rate: $165/hour
Capacity: 6

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!