The first attack happened about 10:05 p.m. in the 11600 block of South Yale Avenue also in West Pullman when a 30-year-old man was on the sidewalk, police said.
An assailant fired multiple shots at the 30-year-old who ran into a nearby yard where he collapsed while the shooter jumped into a black car and sped away.
The 30-year-old, who suffered a gunshot wound to the right side of his chest, was taken to the University of Chicago Medical Center, where he was pronounced dead a short time later, police said.
No one was in custody for any of the attacks and detectives are investigating.
When the 53-year-old approached another person, that person fatally shot him and ran away, police said.
The 53-year-old was dead on the scene, according to police.
Separately, about 12:20 a.m. in the West Pullman neighborhood, a 25-year-old man was shot in the abdomen by a gunman who fled the scene, police said.
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