Among those who have sailed for the club is Robert Halperin, who won an Olympic bronze medal in 1960 and a Pan American Games gold medal in 1963 in yachting, and who 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.
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In addition to the Mackinac race, the Club will host the National Offshore One Design (NOOD) Regatta June 11–13, 2010, the 505 North American Championship June 23–26, 2010, and many other competitive sailboat races.
Mackinac Island is the destination of both the annual Chicago to Mackinac Sailboat Race, run by the Chicago Yacht Club, and the annual Port Huron to Mackinac Boat Race, sponsored by the Bayview Yacht Club of Detroit, Michigan.
Sheldon Clark (1877 - August 15, 1952) was commodore of the Chicago Yacht Club and chairman of the Sinclair Refining Company.
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In 2006 twenty-five T-10s participated in the Chicago Yacht Club's Race to Mackinac (see Chicago to Mackinac Boat Race), a popular 333-mile race along the length of Lake Michigan from Chicago, IL to Mackinac Island, MI.