"CYC" is well known as being the Organizing Authority for the Chicago Yacht Club Race to Mackinac held each July.

CYC also organizes dozens of other sailboat races and regattas throughout the boating season, which is usually considered May 1 to October 31 in the Chicago area.

Among those who have sailed for the club is Robert Halperin, Richard Stearns and William Parks who won an Olympic bronze medal in 1960.

Halperin also won a Pan American Games gold medal in 1963 in yachting, and was also a football player at Notre Dame, Wisconsin, and in the NFL, one of Chicago's most-decorated World War II heroes, and Chairman of Commercial Light Co.[4] As part of the club's centennial celebrations in 1975, Richard and Wendy Van Mell edited The First hundred years : a history of the Chicago Yacht Club, 1875–1975.

In June, the club hosts the SAILING WORLD Magazine's National Offshore One Design (NOOD) Regatta which draws several hundred competitors from around North America.