The crash happened in the Back of the Yards neighborhood's 4700 block of South Ashland Avenue at about 6 a.m., police said.
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A 56-year-old man was driving a passenger van southbound when he tried to turn left, police said. A 71-year-old man was driving a Toyota Camry northbound on Ashland Avenue, and the two vehicles collided.
A 58-year-old man, who was a passenger in the van, was transported to Stroger Hospital in critical condition, police said. Five other passengers were taken to area hospitals with minor injuries. The Toyota Camry's driver was transported to Mt. Sinai Hospital in fair condition.
No citations have been issued and the investigation is ongoing, police said.