The two men were on the street in the 4400-block of W. West End Avenue just before 12:30 p.m. when they both were shot by an unknown person, Chicago police say.
The first victim was shot in the right side and was transported to Mount Sinai Hospital in critical condition.
The other victim was shot in the head and also taken to Mount Sanai Hospital in critical condition.
No one is in custody and Area Four Detectives are investigating.