The five victims remained in critical condition Friday morning.
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Lorenzo Matthews, 11, and Michael Smith, 12, were at the barbershop. The boy's mother said her younger son was shot three times.
Chicago police said two men fired shots into the Gotcha Faded barbershop in the 200-block of North Pulaski Road Thursday at around 6:15 p.m. Barbershop owner Isaac Trenell said he remembers seeing the men come in his shop and thinking they looked suspicious.
"I had like an eerie feeling so when I was talking to the young boy I'm saying, when these two guys leave out I'm going to lock the door behind them because I didn't like how they were looking toward the back," Trenell said.
Police said two men walked into the packed shop, then walked out, pointed guns into the doorway and just started shooting. Trenell said there were close to three dozen people, including a lot of kids, in the shop at the time.
"As I was going to lock the door that's when the shots rang out," he said.
Three boys, ages 11, 12, and 16, were hit by bullets and two other men also wounded.
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Cierra Mobley, the mother of two of the boys injured in the shooting, is still in disbelief.
"It's their first time at the barbershop and it's somewhere that they really wanted to go. They were only there for like an hour before I got that phone call," Mobley said.
Mobley said Lorenzo had surgery late Thursday night.
An unidentified 16-year-old boy was shot in the hip and taken to Stroger Hospital, where he stabilized, police said.
Chicago police also said a 30-year-old man was shot in the arm. He took himself to Loretto Hospital, where he has stabilized.
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A 40-year-old man is stable at Mount Sinai Hospital after being shot in the thigh.
The corner barbershop is a popular spot for neighborhood families and children.
Customer Nicky Triplet said, "Kids always get their haircuts. Three kids got shot? That's, that's ... it's senseless."
A local community activist took this moment to talk about the ongoing violence.
"It's all of our problems and everyone has to take and be invested to make the change in our community and that community change starts today," said Rabbi Michael Ben Yosef.
Police said detectives are poring over video from the barbershop and surrounding blocks, trying to identify the gunmen. A motive for the shooting remains unclear.