The shooting took place 11:21 p.m. in the 7800-block of South Calumet Avenue.
Police said two men were outside when they were approached by five male suspects.
There was an encounter and the two victims were shot, police said. It is not known how many of the suspects were armed or fired.
A 37-year-old man was shot in the chest and pronounced dead at the scene, police said. A 44-year-old man was shot multiple times and was transported to the University of Chicago Medical Center, where he was pronounced dead.
The suspects fled on foot toward 79th Street, police said. Area Two detectives are investigating.
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