It happened at about 3:20 a.m. in the 1200 block of S. Loomis Street, police said.
CPD officers were on foot dispersing a large gathering when they were struck by a driver in a blue car heading westbound in the eastbound lane, police said.
After striking five police officers, the driver drove over the curb, crashed into a CPD squad car, a pole and a fence.
The 18-year-old man driving the car was not injured and was taken into custody.
CPD said they found a gun in the car.
All five officers were taken to local hospitals and are expected to be OK.
Charges are pending.
Ald. Gardiner said police were addressing a so-called "teen takeover."
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About 30 minutes later, a 19-year-old man was shot in the 1100-Block of West Roosevelt Road, police said.
Chicago police did not say if the shooting was related to the large gathering.
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