The males, whose ages were unknown, were standing on the sidewalk just after midnight in the 3500 block of South Indiana Avenue when a red sedan pulled up and someone started shooting from inside the car, police said.
One male suffered two gunshot wounds to the right leg and was transported by paramedics to the University of Chicago Medical Center where he was listed in good condition, police said.
The other victim was shot once in his leg and refused medical attention at the scene.
Police said both victims refused to answer any questions about the shooting.
No one is in custody as Area One detectives investigate.