About Chicago Sailing

Welcome Aboard!

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, J/24 and a J/30. One T10 and four Hunter 326's and some larger boats for luxury charters ('Parvenu') and group charters ('Bumblebee'). 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!

Our Mission

Chicago Sailing’s mission is to make sailing universally fun, safe and achievable. We firmly believe that sailing is more than just sport; it is a way of life and an opening to a bigger world. We intend to share our passion for this lifestyle and support your lifetime of adventure.

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.

Rentals and Charters

Choose from the wide array of 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 Chicago Sailing its unique spirit. Regularly scheduled events include 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.

Continuing Maintenance - Proper Yacht, Inc.

Wouldn't it be great to have a boat valet to handle the many chores associated with making your boat ready for guests or for sea? We will design a maintenance plan suited to the needs of busy boaters. This service includes a power wash of the hull's exterior, chamois wipe-down and engine fluid check. You can also choose from a variety of optional services that meet your needs. Call to set up a program that suits your needs.” It is just flat and we can do more that wash the boat.

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