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The woman was sitting in a parked vehicle early Sunday when someone opened fire, striking her in the head.
The man was walking Saturday night in the 2900 block of West Devon Avenue when someone approached him on foot and fired shots.
The male suffered a gunshot wound to the chest about 5:15 p.m. Saturday in the 6600 block of South Rhodes Avenue.
About 12:20 a.m., two men, 31 and 40, were inside the restaurant in the 100 block of North Wabash Avenue when someone fired into the restaurant and struck them both, Chicago police said.