Police say Kavan Collins was holding a gun when it went off in a home in the city's South Chicago neighborhood.
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Investigators are still working to figure out how Collins got his hands on the weapon.
Police said they questioned one man, who was home when the gun went off, just before 6:30 p.m. Tuesday.
The 5-year-old boy was transported to the hospital for treatment.
Collins was taken to the same hospital in June 2016, after he was shot in the face by a stray bullet and suffered a broken jaw.
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He was walking with his mom in the city's Parkway Gardens neighborhood when he was shot.
Charges have not yet been filed in the latest shooting incident.
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