Chicago fire officials said the incident happened just after 9 p.m. at Cicero and Devon avenues in the Sauganash neighborhood.
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Chicago police said the 5-year-old was in the street when he was struck by a red SUV Jeep that was driving north on Cicero. He was then struck a second time by the driver of a 2013 Volvo also driving north on Cicero, CPD said.
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The driver of the Jeep fled the scene, but the driver of the Volvo stopped and stayed at the scene after the incident.
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CFD would only say that the boy was struck by a vehicle and taken to St. Francis Hospital in grave condition.
Chicago police later said the boy was transported in critical condition.
Major Accidents is investigating, CPD said. It was not clear why the child was in the street at the time of the incident.