The men were standing on a sidewalk about 7:10 a.m. in the 800 block of North Drake Avenue when a male exited a dark color sedan and opened fire in their direction, Chicago police said.
One man, 50, was struck multiple times in the upper thigh and transported to Stroger Hospital in critical condition, police said.
The second man, 25, was also struck in the thigh and taken to the same hospital in good condition, police said.
The shooter returned to the sedan after the attack and fled the scene, according to police.
There is no one in custody.