Police said the shooting happened in the Homan Square neighborhood's 3700 block of West Roosevelt Road just before 11:20 p.m.
A 33-year-old man was pumping gas there when a white Infiniti pulled up, police said. Three people got out and fired gunshots and rifle rounds at the man before fleeing the scene.
Police said the victim, shot nine times in his body, then drove himself to Mount Sinai Hospital, where he is in critical condition.
A 31-year-old woman, who was in the man's vehicle, was shot in her shoulder, police said. She is also in critical condition at Mount Sinai Hospital.
No one is in custody and Area Four detectives are investigating.
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