We firmly believe that sailing is more than just sport, it's a way of life. Sailing opens up a whole new world for you, your friends and family. Our focus is to provide you with easy access to every phase of the sport without requiring boat ownership.

Since 1987, Chicago Sailing has been providing lessons, rentals, charters and racing programs to sailors of all skill levels in and around the Chicago area.

Whether your interests lie in learning to sail, refining your racing skills or just spending an afternoon soaking up the sun, we have a program for you.

At Chicago Sailing, you learn from professionals. You can choose from a well-maintained fleet of J/22s and J/30s, Hunter 326's and some larger boats. You can be certified to bareboat charter anywhere in the world. And you connect with a great group of like-minded enthusiasts at social activities and special events. It's a fun place to hang around. We charge no membership fees or dues. To join, come sail with us!

Certified Sailing Instruction

As a US Sailing certified school, Chicago Sailing is the ideal source to hone your skills whether you're a rank novice or an experienced yacht racer. Our modular program consists of a progressive ladder of individual classes, clearly defined expectations and certifications. Bring your sunglasses and a sense of adventure; we supply the rest.

Great Instructors

The men and women who make up Chicago Sailing's instructional staff are all sailing addicts with strong credentials. Most are US Sailing certified professionals and US Coast Guard licensed. Each has been thoroughly screened for outstanding seamanship and communication skills. You'll find our instructors to be patient, caring guides who will share your enthusiasm and excitement about sailing and each new skill you master.

Choose from the any of the yachts in our fleet. You may rent bareboat and set your own course, or charter a boat so you can relax while one of our Coast Guard licensed captains takes you where you want to go.

Full Services

We love sailing and want to share it with as many people as possible. It's this dedication and passion that gives the club its spirit. Regularly scheduled events include racing leagues, social club sails, firework cruises, barbecues and exciting live-aboard cruises. We're not about bells & whistles, definitely not a fancy clubhouse - just a simple, easy, inexpensive way to get out and enjoy sailing's magic.

Yacht Service - Proper Yacht, Inc.

We're proud to introduce our new marine service venture - Proper Yacht, Inc. Our staff of technicians understands that boat ownership is much more of a marriage than a pastime. And that the care you give your boat is reciprocated. We promise to bring uncompromising quality and care to both Chicago Sailing Club's fleet and the discriminating clients of Proper Yacht.

This year get involved in the action and try something altogether more refreshing with Chicago Sailing.