The crash occurred at about 2:56 a.m. in the 3600-block of North Racine Avenue.
Police said Orlando Matos III, 18, was in a stolen Hyundai and ran a stop sign, crashing into the CPD SUV.
The Hyundai then hit three parked cars while the squad SUV was pushed into a tree, police said.
Two police officers were transported to a hospital with serious injuries, police said.
Matos is facing several felony counts. including aggravated reckless driving and possessing a stolen car.
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