The crash occurred at 55th Street and Central Avenue near Midway.
Police said a Ford Fusion was driving eastbound when the driver made a U-turn and struck a westbound Hyundai Palisade.
The 28-year-old man driving the Ford Fusion was transported to Stroger Hospital, where he later died, police said.
A 31-year-old passenger in the Ford Fusion was transported to Advocate Christ Hospital in critical condition, police said.
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The 29-year-old man driving the Palisade was transported to Advocate Christ Hospital in fair condition, police said.
Three passengers in the Palisade were also transported to hospitals, a 20-year-old woman in unknown condition, a 32-year-old woman in fair condition and a 17-year-old girl in fair condition, police said.
No other injuries were reported and the Chicago Major Accident Investigation Unit is investigating.