Officers were conducting a traffic stop in the 1400-block of South Michigan Avenue at about 8 p.m., police said.
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A Hyundai Sonata made a sudden U-turn as officers approached and hit two other vehicles, police said.
The driver of the Hyundai, a 22-year-old man, was transported to Northwestern Memorial Hospital, where he was pronounced dead. Authorities have not released his identity.
Two passengers in the Hyundai, an 18-year-old woman and a 21-year-old man, were transported to Stroger Hospital in fair condition.
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A 32-year-old woman driving an SUV and a 13-year-old girl and 14-year-old boy who were passengers in her vehicle were transported to Stroger Hospital in fair condition, police said.
An 18-year-old man driving an Infiniti was also transported to Stroger Hospital in fair condition.
The Chicago Police Major Accidents Unit is investigating the crash.