The pair was sitting in a parked car around 12:14 a.m. in the 7400 block of North Wolcott Avenue when a gunman walked up and started shooting, according to police.
A 21-year-old man was shot in the head and body and was taken by paramedics to St. Francis Hospital where he was pronounced dead, police said. He has not yet been identified by the Cook County Medical Examiner's Office.
A 20-year-old man suffered gunshot wounds to the abdomen and leg and was taken to St. Francis Hospital where he was listed in fair condition, officials said.
No one is in custody as Area Three detectives investigate.