Learn, Charter, Rent

See Chicago Like Never Before

Who We Are

On behalf of everyone here at Chicago Sailing, Welcome!  We pride ourselves on being Chicago’s premier sailing school and charter facility.  With our wide array of offerings we are a complete one stop shop for all of your sailing needs.  No matter what your sailing goals are we will work with you to get you out on the water!

The Chicago Sailing Team

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Our Services

From learning to sail, to fractional ownership we have all of your sailing needs covered. Let us help you experience the city and the lake like you have never seen them before. Our fleet of more than 20 vessels ranging from 22'-53' and full time on site staff will make sure you and your guests have the best sailing experience possible!

Sailing Lessons
Learn to master the wind and the waves with our sailing lessons. Options range from beginner to advanced levels
Sailing Vacations
Set sail for a new port with one of our sailing vacations! With options in the midwest and the British Virgin Islands, we have the perfect trip for you!
Seasonal Memberships
Get out on the water more while paying less! We have several seasonal sailing options that make sailing more accessible.
Captained Charters
Want to sit back and relax while the skyline goes by? No problem! Enjoy the ride as one of our USCG licensed captains takes the wheel.
Group Outings
Want to make a splash with your next client meeting? Looking for a fun bachelorette/bachelor party idea? We have you covered!
Multi-Day Adventures
Set sail for a change of scenery. Join us on a trip back from the scenic waters of Mackinac Island, or how about a weekend trip to Michigan?

Latest News

Few cities embrace St. Patricks day like Chicago does, and even less companies embrace it like Chicago Sailing does! We have a strong passion for all things Irish here at Chicago Sailing, represented in our annual Irish J-1 staff, and our passion for Guinness 🙂 We deiced to take some friends and Family of the...

Chicago is the perfect Bachelorette party destination in the summer, so why not take advantage of it’s most beautiful feature, Lake Michigan! Make your outing stress free and relax on the waters of Lake Michigan on one of our luxury charter boats! Kick back in the sunshine and enjoy some cocktails onboard while you and...

Well the boat show is over, that means we are creeping closer to the 2018 sailing season!  It’s hard to believe that we are only 58 days away from moving the houseboat back to Belmont, and only 93 days from our opening day for 2018!  We have a lot of exciting events & opportunities planned...

It is with great excitement that we announce the newest addition to our fleet, Naida!  Built in 1935 on the banks of the North Branch of the Chicago River by Henry Grebe Boatworks, she is a real classic Chicago yacht.  Our Dir. Of Ops. Graham found her outside Seattle in Olympia, WA and knew she...

Our updated Gift Card portal is now live!  It’s never been easier to give the gift of sailing, gifts are available for specific offerings like lessons & events, or for a custom monetary amount. Delivery is instant via email, which makes it a perfect solution for last minute gift giving. Check it out here!

Here at Chicago Sailing we are always looking for ways to make your sailing experience with us more enjoyable.  With that in mind we have updated the sheet rigging on the Hunter 326s! By adding two winches to the back of the cockpit surround, and re-locating the mainsheet to the bimini arch, the captain now...

Contact Us

Questions? No problem! We are here to help you get the most out of your time on the water. Feel free to drop us a line at the email below, or give us a call!

2 W Belmont Harbor Dr, Chicago, IL 60657
(773) 871-7245

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