The two were standing in the 3500-block of West 61st Place in the city's Chicago Lawn neighborhood just after 4:20 p.m. when a gray vehicle pulled up and two male suspects started shooting at them, police said.
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The man was shot and taken to Advocate Christ Medical Center in Oak Lawn in critical condition. He later died.
The 14-year-old was shot and pronounced dead on the scene, police said.
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The Cook County Medical Examiner's Office identified them as 14-year-old Juan A. Medina Jr. and 65-year-old Mario Medina. They both lived in the same block where the shooting took place, the medical examiner's office said.
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The suspects drove west on 61st Place after the incident, CPD said.
No one was in custody later Tuesday, and Area One detectives are investigating.
Crisis responder and victim advocate Andrew Holmes said the victims are related.
Red crime scene tape draped in front of a festive light display marked the heartbreak for one Southwest Side family ahead of the holiday season.
"We have lost two family members here on this block," Holmes said. "Detectives are going block-to-block trying to see and figure out if they can get a license plate or surveillance footage."
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Nearly 20 evidence markers with bullet shell casings were scattered on the street Tuesday.
"There was some type of altercation here. Some individual came to visit another individual, gray car pulled up; they discharged that weapon, striking the 14-year-old," Holmes said. "We don't know if he knew the individuals or what was the relationship between the people that was coming to visit him, just don't know."
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