A male victim was pulling into a garage parking lot just before 3:40 a.m. in the 1100-block of South Delano Court when a black Jeep and white sedan followed him into the structure, CPD said.
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A total of five male suspects exited the Jeep and sedan and pulled out guns, according to CPD.
The victim, a concealed-carry holder, also pulled out a gun, and a shootout ensued, police said.
The suspects then ran back to their vehicles and drove away.
The victim was shot in the right leg and suffered a graze wound to the head.
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He was taken to Northwestern Memorial Hospital in good condition.
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No one was in custody later Monday morning, and Area Three detectives are investigating.
Several minutes earlier, three male suspects in a black Jeep got out of the vehicle and struck a 48-year-old woman in the back of the head in the 700-block of South Wells Street and demanded her property, CPD said.
They took her Chrysler 300 and other belongings.
No one is in custody, and Area Three detectives are investigating.
CPD would not confirm if the incidents were connected.