The Waukegan Yacht Club was founded in 1927 to promote yachting, yacht racing and good fellowship among yachtsmen on Lake Michigan. The club has grown from its original home, a 20 ft x 60 ft houseboat, to its present one-story, full-service facility in Waukegan Harbor.

The Waukegan Yacht Club offers many boating and social events to its members. All events are organized and run by volunteer member committees and typically include: a New Year's Eve Party, St. Patrick's Day Party, Blessing of the Fleet, Chicago to Waukegan Sailboat Race, WYC Invitation Regatta, Commodore's Ball and the Children's Christmas Party. Other events fill out a full schedule of activities for the participation and enjoyment of the membership and their families.

The Waukegan Yacht Club is well known for its sailing program which runs all year except when the harbor is frozen over. The club promotes a Junior Sail Program for children ages nine through eighteen years. Participants in this program learn sailing theory, seamanship, self-reliance and sportsmanship. The adult sail program includes Wednesday night, JY15 on Thursday night and Saturday race programs as well as participation in various association regattas. Frostbiting in Waukegan Harbor during the winter rounds out the program.