The victim, who has been identified as 25-year-old Elliott Brown, was a former De La Salle High School basketball and football star.
According to police, the two victims were driving eastbound on the Skyway into Indiana in a BMW coupe when someone in a black SUV opened fire around 1:30 p.m. Police say the SUV continued driving into Indiana.
Police said a 23-year-old female victim was shot in the left arm and was taken to Northwestern Memorial Hospital where she is in stable condition. Brown was shot multiple times and killed.
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Police say they believe the victims and the people in the SUV had contact prior to the shooting, but the motive is unclear. No one is in custody.
A seven-mile stretch of the eastbound Skyway was shut down for more than four hours as police investigated, but all lanes reopened just before 5:30 p.m.