Police said the shooting happened in the South Shore neighborhood's 2100-block of East 71st Street just after 6:45 p.m.
Two men, 53 and 74 years old, were standing near an alley when someone fired shots, police said.
The 53-year-old man, shot in his back, was transported to the University of Chicago Medical Center, where he was pronounced dead.
The 74-year-old man, shot multiple times in his body, was transported to the same hospital in good condition.
No one is in custody and Area One detectives are investigating.
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