The men were outside about 9:30 p.m. when someone inside a vehicle fired shots in the 7000 block of South Vincennes Avenue, Chicago police said.
A 52-year-old man was shot in the arm and lower back and was taken to the University of Chicago Medical Center in critical condition, police said.
Two others, 44 and 57, were struck in the leg, police said. The 44-year-old was taken to University of Chicago Medical Center and the other was taken to St. Bernard Hospital, where they were in fair condition.
A fourth man, 65, was struck in the arm and also taken to the University of Chicago Medical Center, police said.
No one is in custody as Area One detectives investigate.