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The man ran into traffic before being struck by a Toyota Prius, police said.
The man was found unresponsive in the water then taken to University of Chicago Medical Center in critical condition.
The boat, carrying 16 people, capsized about 7:30 p.m. Officials are searching Lake Michigan for one person who was unaccounted for.
A 16-year-old boy and a 40-year-old man died after being shot about 10:40 a.m. Friday in the 2500 block of West 46th Street, police said.