Chicago police said it happened early Saturday at 3:10 a.m. near 53rd Street.
A 20-year-old woman was driving a gray sedan with two other passengers, northbound in the southbound lane when they hit a white sedan with three people travelling southbound, police said.
The impact caused the white sedan to crash into another white sedan that was heading southbound, police said.
The female driver of the gray sedan died at the hospital, police said. She was later identified by the Cook County Medical Examiner's Office as 20-year-old Deja Palmer of Chicago.
A female passenger was transported to Provident Hospital in serious condition.
A male driver of the first white sedan is in serious condition at U of C hospital. His two male passengers are also hospitalized, police said.
The male driver of the third vehicle is hospitalized with head and neck injuries, CPD said.
The medical examiner later said one of the people injured died. They did not say which passenger.
Traffic citations are pending, police said.