The crash occurred at about 9:15 p.m. in the 3600-block of West Columbus Avenue, police said.
A black Nissan was traveling north on Columbus when police said it struck a Mazda head-on in the intersection at 83rd Street. Investigators said the Nissan was attempting to make a left turn.
A third vehicle was also involved in the crash when it was rear-ended by the Nissan, police said. A fourth vehicle traveling southbound then also hit the vehicles, police said.
Two men in the Mazda were transported to Advocate Christ Hospital in critical condition, where one of them later died.
The man driving the Nissan was transported to Advocate Christ Hospital in serious condition.
Two women inside of the third vehicles suffered minor injuries and were transported to the University of Chicago Medical Center in fair condition. The driver of the fourth vehicle suffered minor injuries and was taken to Little Company of Mary Hospital in good condition, police said.
Area One detectives are investigating.
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