The group was standing near the street in the 200 block of East 35th Street around 3:14 p.m. when someone approached them, fired shots and fled the scene, Chicago police said.
A 44-year-old man who was shot in the arm and a 65-year-old man who was struck in the arm and leg were both taken to the University of Chicago Medical Center in good condition, police said.
Police said another male suffered a graze wound to the hand and was transported to Mercy Hospital in good condition.
A fourth male was struck on the body but refused treatment, police said.
No one is in custody and Area Detectives were investigating.