Police said the shooting happened in the Englewood neighborhood's 6100-block of South Justine Street just after 9:10 p.m.
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Officers responded to a call of shots fired and found the victims in the alley.
A 35-year-old man, shot twice in the head, was pronounced dead on the scene.
A 60-year-old woman, shot once in the head, was transported to Holy Cross Hospital in critical condition.
A 52-year-old person, shot in the thigh, was transported to Stroger Hospital in critical condition. CPD did not immediately provide information about that victim's gender.
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A 64-year-old man, shot in the arm, was transported to the University of Chicago Medical Center in good condition.
Witnesses told police they saw a male suspect shooting at the mouth of the alley and fleeing the scene.
Chicago Street Pastor Donovan Price said he is tired of all the violence.
"Another mass shooting. Of the many things that have been going on, children shot, mass shootings, all in a matter of four days or so and it's not summer and it's not even winter yet, but it's still killing going on," Price said.
No one is in custody and Area One detectives are investigating.
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