The crash occurred at Jackson Boulevard and Francisco Avenue, involving an unmarked police vehicle and a marked squad car. The unmarked vehicle crashed through a fence before striking a tree and coming to a stop.
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Both vehicles were apparently in pursuit of a suspect who reportedly fired several shots a few blocks away in the area of Ferdinand Street and Drake Avenue, at about 10:19 a.m.
A number of officers joined the police pursuit until it was called off.
Four of the five officers involved in the crash were able to walk to ambulances. While two are listed in critical condition, police said none of the injuries are considered life-threatening.
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Two of the officers were transported to Stroger Hospital in critical condition and three others were transported to Rush Medical Center in fair condition, authorities said.
Police said the suspect's vehicle was later found empty and abandoned in the 2600-block of West Adams Street with an extended magazine inside. No one is in custody.