CHICAGO SAILING LOGO

SCROLL

EXPERIENCE THE WINDY CITY

Escape the noise and the bustle of the city without leaving your zip code.  Chicago Sailing offers a variety of boats and activities that make getting off land and onto the lake easier than ever.  With lessons, charters, and rentals we can help you experience the city and the lake like you have never seen them before.  Our fleet of over 20 vessels ranging from 22'-53' and staff of US Sailing & USCG certified instructors and captains means you will always have a enjoyable and safe experience on Lake Michigan.

WHAT'S NEW?

SAILING OPTIONS

SAILING LESSONS

SAILBOAT CHARTERS

SAILBOAT RENTALS

LESSONS CHARTERS RENTALS

Learning to sail is fast, easy, and fun at Chicago Sailing. You will become an accomplished, confident skipper in just a few sessions of on-the-water training. Our classes are comprehensive and certified to the highest standard in the industry, those of US Sailing. We also have the largest fleet of training vessels in the greater Midwest, meaning that we offer the most opportunities for on-the-water training. Soon you will be joining the thousands of sailors who have launched their sailing adventure at Chicago Sailing.

​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.

Chicago Sailing is Chicago’s only public sailboat rental facility, providing a wide range of boats for you and your friends to enjoy. Rentals are available from morning til dusk, seven days a week, so you can enjoy sailing as often as you like. Take your friends sailing and show them the skyline!

Sign Up For Our Newsletter!
Chicago Sailing Gift Cards

SEE CHICAGO LIKE NEVER BEFORE

CHICAGO SAILING LOGO
INSTAGRAM BUTTON TWITTER FB
@chisail @chisail Like Us!
contactus@chicagosailing.com 773-871-SAIL