Welcome to Go Sailing Chicago

Whether you want a romantic sailboat charter for two under the stars, to sail along the Chicago skyline with friends, to learn sailing with the friendliest instructors in the city, or enjoy quality time with family while the sun sets, Go Sailing Chicago has the right Chicago sailboat charter or sailing lesson option for you.  We offer a range of sailboats including cruisers, racers, and luxury boats.

We sail in Chicago from the break of dawn until the deep of the night 7 days a week, so the schedule is always right.  We sail only with the top United States Coast Guard Master Captains and US Sailing and ASA Certified Instructors the city has to offer, which ensures your safety. And our downtown Chicago location can’t be beat. 

We love sailing so much that if by the time you are done looking through our site and don’t find the sailboat charter or sailing lessons option you want, contact us so we can refer you to another Chicago sailing site or company to help out.  That’s what we do here at Go Sailing Chicago, we go sailing and we want you to join us.   

Use the links to the right to take a look at our Chicago sailboat charter options and our Chicago sailing lessons options, then call or use the online reservation request to secure your reservation.  Now you can text us your request too.  Just text us at 773.710.7245 (SAIL) and request your reservation today.  Don’t forget about our weekday sailing special!

Now let’s Go Sailing Chicago!

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counting down to the first sail!