It happened in the Englewood neighborhood near West 59th Street and South Ashland Avenue. Police officers were fired upon, but were not injured, CPD said.
A Chicago Fire Department spokesperson said a 16-year-old boy walked into a firehouse at West 59th Street and South Ashland Avenue after being shot at about 7:22 p.m. He was transported to the University of Chicago Medical Center in fair to serious condition.
A few minutes later, CFD responded to a 16-year-old boy and a 25-year-old man, who had been shot, in a vehicle at West 59th Street and South Wells Street.
CPD said the two male victims were in a vehicle that fired shots at a marked squad car after the initial shooting.
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The vehicle crashed in the 5900-block of South Wells Street, and all five in the car were taken into custody.
CFD said the second teen boy was taken to the University of Chicago Medical Center in critical condition. The man was taken to the same hospital in good condition.
Police did not fire any shots, according to CPD.
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