Police said the recruit was driving with one passenger westbound on Gunnison Street near Rockwell Street in Lincoln Square at about 12:13 a.m. when multiple shots were fired at them.
As the victims tried to escape, their vehicle careened into several parked cars at Talman Avenue.
"I just open the window to see what's going on. I see the Mustang crash into the SUV and I see how it turns around," said neighborhood resident Luis Mejia.
The police recruit, a 21-year-old man, suffered a graze wound to the back and was transported to Illinois Masonic Medical Center, police said.
The passenger, a 24-year-old man, was not injured.
Donicino Perez's Jeep was among the vehicles damaged in the crash.
"I hear 'boom,' and I wake up, and I listen to people running outside and talking, and that's why I go outside for what's going on and look at my car," Perez said.
Another man, who wanted to remain anonymous, found out his car was damaged, too.
"He did not want to show his face, but there is a shot of his back," he said. "He's a white guy with glasses and a beard. I heard a bunch of car horns going off last night, but I certainly didn't think my car was ruined."
It's unclear if the attack was random or targeted.
No one is in custody and Area Three detectives are investigating.
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