Police said the shooting happened on the sidewalk in the Austin neighborhood's 500-block of North Leamington Avenue just after 11:30 p.m.
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Two people took out guns, and one fired shots, police said.
Police said a 44-year-old man dropped a handgun after he suffered a gunshot wound to his eye. He was transported in critical condition to Stroger Hospital, where he was pronounced dead.
A 50-year-old man suffered a gunshot wound to his back and three more to his arm, police said. He was transported to Stroger Hospital in good condition.
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Police said a 27-year-old woman later walked into Loretto Hospital with a graze wound to her cheek. She was listed in good condition before being treated and released.
Officers found a handgun on the scene. No one is in custody and Area Four detectives are investigating.
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