Welcome to Go Sailing Chicago

Whether you want a romantic sailboat charter for two underneath the stars, to sail along the Chicago skyline with friends, learn to sail with the best instructors in the city, Go Sailing Chicago has a Chicago sailboat charter or sailing lesson for you. You can choose from a range of sailboats including cruisers, racers, luxury sailboats in 3 Chicago locations. 

We sail in Chicago from the break of dawn through the late hours of the night 7 days a week. The schedule is always right for your Chicago sailing needs. We sail with the friendliest United States Coast Guard Master Captains and US Sailing/ASA Certified Instructors the city has to offer ensuring your safety. Our downtown Chicago locations can’t be beat.

Use the links at the top of the page to take a look at our Chicago Sailboat Charters, Chicago Sailing Lessons, or our ALL NEW Helm Time! You can then call, text, or book now to secure your reservation.  Note: Online reservations must be made at least 7 days in advance. If you have immediate needs, please email or text us. contact us. One of our staff will be sure to do whatever we can to meet your needs.

Now let’s Go Sailing Chicago!

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Book any of our Chicago sailboat charters or sailing lessons by April 1 and receive $50 off! 

Use promotion code 4113 at checkout.

“We were able to easily schedule, plan and charter the sailboat of our choice for the time we wanted all online and via e-mail. We arrived, met Captain Ben and had a really relaxing day on the Lake. Ben was highly knowledgeable and very patient in showing us the ropes of sailing (in a casual way, as this was not a lesson, but a pleasure cruise).  We asked him lots of questions and he was very patient with us in teaching us whatever we wanted to know. He actually gave each of us a chance to steer the boat while he manned the sails. It was a gorgeous day on the water and we had so much fun. We'd highly recommend Go Sailing Chicago to anyone looking to do something exciting in the city, yet different and memorable.”   - Adam C., Chicago, IL

Counting down to the first sail!