The incident occurred at about 10:25 p.m. in the 5700-block of North Washtenaw Avenue in West Ridge.
Police said tactical officers were investigating a stolen sedan that was parked and unoccupied when a dark-colored sedan with two men and a woman pulled alongside it.
The two men got out of the dark-colored sedan and attempted to enter the stolen sedan, which appeared to be a white BMW, when officers approached, police said.
One man fled on foot while the other got back into a sedan, police said. After directing him to get out of the vehicle, police said the man refused and there was a struggle.
During the struggle, police said the man accelerated the car, dragging the officer. The officer fired their gun and struck the man in the head while the vehicle crashed into an unoccupied parked car, police said.
The wounded man was taken to Illinois Masonic Medical Center, where he was pronounced dead.
He has not yet been identified.
An officer suffered minor injuries and was taken to a hospital, police said.
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The stolen vehicle was towed away Wednesday.
"I'm glad the cop wasn't hurt," neighbor David said. "I'm glad the cop got the guy. I'm glad I wasn't outside when it happened, but what are you going to do?"
David said the stolen vehicle has been in the area for the past couple days, coming and going at different times. He said he didn't recognize the man behind the wheel.
"The last three days I think," David said. "It was parked cockeyed. It took my spot that I just shoveled out, so."
Those who woke up to gunshots were thankful police were nearby.
"My wife woke up and saw it," David said.
A woman was taken into custody and two firearms were recovered at the scene, police said.
The Civilian Office of Police Accountability is investigating the shooting.
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