The three men were outside when someone fired shots about 5:40 a.m. in the 3800 block of South Wentworth Avenue, Chicago police said in a statement.
One man, 24, was shot several times and died at the University of Chicago Medical Center, police said.
Another man, 22, was shot twice in his chest and taken to the same hospital, where he was listed in critical condition, police said.
A third man, 25, was in serious condition at the University of Chicago Medical Center with gunshot wounds to his neck and back and a graze wound to the forehead.
No arrest was made, police said.