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Officials said conditions on the water were "pretty nice" in the morning, but the wind picked up later in the day.
Chicago authorities say two people are dead, another is injured and divers are searching for a fourth, following two separate boating accidents.
Authorities say fishing boat capsized around 9:30 a.m. Sunday on the Little Calumet River on the city's South Side.
A 62-year-old man was pronounced dead just before noon. His name wasn't immediately available.
Divers were searching for the second person who was on the 15-foot fishing boat that capsized about 300 feet from shore.
In the other incident, Chicago police spokeswoman Gabrielle Lesniak says a sailboat overturned around 10:15 a.m. on Lake Michigan near DuSable Harbor.
One person is dead and another was transported to Northwestern Memorial Hospital.
Further details weren't immediately available.