The shooting happened at about 2:46 a.m. on Sunday in the 2800-block of N. Normandy Avenue.
Two men, 45 and 25, were arguing with four people, Chicago police said.
The altercation became physical when the offenders began shooting at the victim's before fleeing in different vehicles.
The 45-year-old was shot multiple times in the head. He was taken to the hospital in critical condition.
The 25-year-old was shot twice in the head. He was rushed to the hospital in critical condition.
There is no one in custody.
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