One of the drivers fled from the scene while the other stayed, police said.
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The incident occurred at about 12:58 a.m. in the 4100-block of West Irving Park Road, right near the Kennedy Expressway and the CTA train and bus stops.
Police said the 55-year-old man was crossing the street when he was struck by a gray pick-up truck that left the scene. He was then struck by a black Jeep, which stopped at the scene, police said.
The man was transported to Illinois Masonic Hospital in critical condition, police said.
No citations are pending against the Jeep driver, police said.
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This stretch of road has a CTA Blue Line stop, a Metra platform and the expressway, leading to a dangerous combination of drivers and pedestrians.
"I mean it's crazy over here," said Gail Arciniega. "Every time I'm here. I've done it myself."
"It makes me sad, because I feel like there are signs for a reason. This is city living," said Rosette Cordero. "I just try to make sure I follow the rules, because sometimes drivers do not."
Area detectives are searching for the driver of the pick-up truck and any surveillance video in the area.
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