Around 12:48 a.m., the 38-year-old was driving eastbound in the 3100 block of West Roosevelt Road when a white Dodge Charger pulled up and someone inside started shooting at him, police said.
The man's car crashed into the bus stop where he exited the vehicle with multiple gunshot wounds, police said.
He was struck in the chest and bicep and entered a business where police applied a tourniquet before paramedics took him to Mount Sinai Hospital, police said. He was listed in critical condition, officials said.
The Charger drove away northbound on Kedzie Avenue.
No one is in custody as Area Four detectives investigate.