Police said the shooting happened in the Bronzeville neighborhood's 4500-block of South Evans Avenue just before 12:30 a.m.
A 35-year-old man, shot in his head, was transported to the University of Chicago Medical Center, where he was pronounced dead.
Another man, 38, was shot in his chest. He was transported to the same hospital in critical condition.
A 26-year-old woman, shot in her buttocks, was also taken to the University of Chicago Medical Center in good condition.
Police believe multiple shooters fired at the victims before fleeing the scene.
There is no one in custody and Area One detectives are investigating.
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