The shooting occurred at 51st Street and Michigan Avenue at about 12:10 a.m., police said.
The victims were standing on the sidewalk when someone in a gray vehicle fired shots.
A 26-year-old man was transported to University of Chicago Medical Center in critical condition after being wounded in the head.
Four others wounded in the shooting were transported to hospitals in stable condition: A 15-year-old boy was wounded in the leg and transported to St. Bernard Hospital; a 50-year-old man was wounded in the back and taken to Stroger Hospital; a 33-year-old man was wounded in the lower back and taken to University of Chicago Medical Center and a 31-year-old man was wounded in the body and transported to University of Chicago Medical Center.
No one is in custody. Area Central detectives are investigating.