The crash occurred at about 2:56 a.m. in the 3600-block of North Racine Avenue.
Police said a marked CPD squad car was driving southbound on Racine Avenue when a Hyundai Elantra which was previously reported stolen disregarded a stop sign and crashed into the squad car.
The Hyundai then hit three parked cars while the squad car was pushed into a tree, police said.
Two police officers were transported to a hospital with serious injuries, police said.
The driver of the Hyundai, an 18-year-old man, was transported to Illinois Masonic Medical Center in critical condition and was subsequently taken into custody, police said. Charges are pending.
No other injuries were reported.