The shooting took place at about 10:40 p.m. in the 10-100-block of North Western Avenue.
Police said two men, ages 24 and 49, were standing outside when a suspect shot at them from a vehicle driving by.
The 24-year-old man was shot in the legs and the head and transported to Stroger Hospital in critical condition, police said.
The 49-year-old man was shot in the abdomen and buttocks and transported to Stroger Hospital in fair condition, police said.
No one is in custody and Area Three detectives are investigating.
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