A delivery driver was sitting in his car near 45th Street and Ashland Avenue when he was shot in the face and ear, police said.
He was transported to Mt. Sinai Hospital initially in good condition.
The other victim, an 18-year-old who was standing on a sidewalk, was also shot in the thigh. He was transported to Stroger Hospital, also initially in good condition.
Police said no one is in custody and area detectives are investigating.
At least 25 people have been shot, six fatally, in Chicago weekend violence.