Sail Chicago

  • IL


P.O. Box 101069
United States

About Us

Sail Chicago is a community-based, all-volunteer sailing program providing sailing instruction and affordable access to sailing on Lake Michigan for adults 18+ in the Chicago area. We own and maintain a fleet of sailboats in the Chicago Harbor system. We have classes for beginner through advanced sailors, as well as ongoing educational activities throughout the year.

Visit our website to see upcoming news and events

Learn To Sail

Sail Chicago has taught thousands of adults to sail affordably since our program began in 1958. Basic, Intermediate, and Skipper Prep sailing lessons are aboard our small keelboats in many harbor locations in downtown Chicago. Our instructors are Sail Chicago-certified sailors instructors are experienced, many of who are US SAILING Basic Keelboat Instructors.


We keep our boats at Chicago's 2 premier harbors: Monroe Harbor and Belmont Harbor. Look below for information on how to find us there. Click under the maps to get more details and directions from Google.


The Sail Chicago fleet began with the purchase of a brand new Rhodes 19 design in the late 1950's. Today we and operate a sailboat fleet of 10 sailboats. Our fleet is comprised of Ideal 18s, Rhodes 19s, Colgate 26s, and a Hunter 34.

We are a non-profit, community-based sailing program that allows our members to cooperatively use and maintain a fleet of sailboats without the severe financial burden typical of individual ownership. The Sail Chicago program is designed to provide a reasonable cost alternative (or enhancement) to boat ownership on Lake Michigan.

New Members

You have 2 ways to sail with us this summer: either join our club with the New Member Package ($400) or take us for a test drive with the Sail Into Summer Package ($250).

Sail Into Summer Package: * A two-hour Pre-Sail orientation.

  • A four-session on-the-water sailing course geared to your level of sailing experience (basic, intermediate, or advanced).
  • This is a limited time opportunity, register now to reserve your space!

New Member Package: * With the new member package you get the same class instruction as the Sail Into Summer PLUS numerous opportunities to get out on the water for free. All of our members get unlimited access to free club sailing with our "Tiller Time."

  • You can also sail for free on our members only cruises.
  • You also will be invited to all of our club social events like barbeques down at the dock or dinners at the yacht club.