The attempted carjacking and shooting happened in the 6400-block of Cicero Avenue at about 7:45 p.m., police said.
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Police investigated the incident around a parking lot of a Lou Malnati's restaurant near Midway Airport.
Authorities say the 34-year-old victim was sitting in his vehicle when he was approached by multiple male offenders who took out guns and demanded his car.
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According to police, the victim and one of the offenders began to struggle outside the vehicle, then one of the offenders shot the victim several times. The car was not taken.
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The victim was transported to Advocate Christ Hospital in serious condition, police said.
No one is in custody in connection with the shooting.
A spokesperson for Lou Malnati's says that no employees were hurt. They say they are cooperating with the police as the investigation continues.