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 dreams are we will work with you to accomplish your goal and get you out on the water!

The Chicago Sailing Team

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
Already an old salt? Skipper your own boat and show your guests the ropes while you cruise along the beautiful Chicago Skyline
Fractional Ownership
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!
Break the mold of what a team outing should be! Sailboat racing is an exciting and unique way to get your team to bond and learn new skills together!
Wine Tastings & Events
What's better than a sunset sail? A sunset sail with a carefully curated selection of wines! Our Wind & Wine events make perfect date nights, vacation outings, or even gifts!
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

Brrrrrrrr. It sure has been cold these past few weeks here in Chicago, that must mean one thing…. The boat show is near! For those who have never attended before, the Chicago Boat, RV, and Sail show marks the beginning of the downhill run towards the start of the sailing season, it is a great...

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...

What a year 2017 has been for Chicago Sailing and our customers.  Looking back on the summer it is hard not to feel sentimental, here at CS we made many new friends & customers, not to mention we saw many new staff members who joined our team.  We had lots of fun and enjoyed every...

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...

Learn More

Learn more about Chicago Sailing and our wide variety of offerings!


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

Say Hello!