SEE CHICAGO LIKE NEVER BEFORE
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 land and onto the lake easier than ever. From lessons to captained charters, even rentals we can help you experience the city and the lake like you have never seen them before. With a fleet of over 20 vessels ranging from 22'-53' and a US Sailing certified staff we make it easier than ever to learn, rent, and charter in the windy city.
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!