Police said the shooting happened in the Belmont Central neighborhood's 6000-block of West Belden Avenue just before 2 a.m.
The men, 25 and 29 years old, were walking outside when someone shot at them, police said.
The 25-year-old, shot in the head, was transported to Loyola Hospital, where he was pronounced dead.
The 29-year-old, shot in the back and shoulder, is listed in good condition at Christ Hospital.
Police said the shooter may have been traveling in a red vehicle when the shooting happened.
There is no one in custody and Area Five detectives are investigating.
Police did not immediately provide further information about the shooting.
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