Jon Santarelli, of Chicago's Lincoln Park neighborhood, is an experienced sailor and one of more than 2,500 participants in this year's race through Lake Michigan to Mackinac Island.
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Rescue efforts were suspended before 10 p.m. after seven hours of searching.
According to the Chicago Yacht Club, which organizes the annual 333-mile race, the Imedi and its crew of thirteen were in the last wave of sailboats to start.
While there were strong winds and high waves reported on Lake Michigan on Saturday, race officials do not believe bad weather led to the accident.
"They're the fastest boats that go out and they're the most ocean-ready boats that sail this race. They're purpose built to compete in challenging conditions," said Jay Keyhoe, of the Chicago Yacht Club. "These sailors are trained. They practice man overboard. They practice sailing in big breeze. The conditions were not extremely challenging."
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It was immediately unclear how Santarelli fell into the water.
Authorities were called at about 2:45 p.m. about the person overboard located roughly 4-5 miles northeast of Navy Pier in Chicago.
The Chicago Fire Department's marine unit, the U.S. Coast Guard and civilian boats searched the area. Several of the competing boats suspended their race to help with the search and rescue, officials said.
The Coast Guard said Santarelli was reported to have been wearing a life vest and was last seen swimming towards a flotation device that was thrown into the water to try and help him.