The 38-year-old driver was driving eastbound in the 3100-block of West Roosevelt at about 12:48 a.m. when a white car approached and someone inside fired multiple shots at the victim's vehicle, police said.
The victim was wounded multiple times and then crashed into a bus stop, police said.
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The victim was transported to Mt. Sinai Medical Center in critical condition with wounds to the chest and bicep, police said.
The suspect's vehicle fled northbound on Kedzie Avenue.
No one is in custody and Area Four detectives are investigating.