The shooting took place at about 5:19 a.m. in the 3100-block of West 59th Street.
Police said 57-year-old man was driving when someone in a silver or gold sedan pulled alongside and someone inside opened fire.
Police said the victim was shot in the head and then crashed into a building. The victim was transported to Advocate Christ Hospital in critical condition.
A 24-year-old-man who was a passenger was not shot but was transported to Advocate Christ Hospital in good condition, police said.
Police said the suspect's vehicle fled in an unknown direction.
No one is in custody and Area One detectives are investigating.
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