The men, 43 and 46, were outside just before 1 p.m. when someone started shooting at them in the 4800 block of West Washington Boulevard, according to Chicago police.
The 46-year-old was shot multiple times across the body and was transported to Mount Stroger Hospital where he was pronounced dead. His identity has not yet been released by the Cook County medical examiner's office.
The 43-year-old was also struck several times in shooting. He was taken to Mount Sinai Hospital where he was listed in critical condition.
A witness told police the shooter fled the scene on foot.
No one is in custody as Area Four detectives investigate.