The crash happened on Saturday at about 10:25 p.m. near the intersection of 64th and Cottage Grove Avenue in Woodlawn.
Three vehicles were involved in the crash; an SUV, a Volkswagen sedan and a Chevy SUV, police said.
The drivers of the SUV and Volkswagen were involved in a previous crash and were driving to the police station to make a report when they crashed with the Chevy.
A 44-year-old woman was driving the Chevy. Chicago fire took her to the hospital where she later died.
The Chevy passenger, a 43-year-old woman, was taken to the hospital with critical injuries.
The man driving the SUV was also taken to the hospital with serious injuries.
The woman driving the Volkswagen was taken to the hospital, she is expected to be okay.
CPD's Major Accidents unit is investigating.