The group was standing on the sidewalk around 1:43 a.m. in the 9100 block of South Harper Avenue when someone in a black sedan started shooting, according to police.
A 57-year-old woman was struck in the head and a 77-year-old man suffered a gunshot wound to the back, police said. They were both transported by paramedics to the University of Chicago Medical Center where they were listed in critical condition.
A third victim, a 59-year-old man was shot in the arm and taken to Advocate Christ Medical Center. He was listed in good condition.
No one is in custody as Area Two detectives investigate.