The pair was standing in the parking lot of a gas station around 9:16 p.m. in the 3600 block of West Grand Avenue when a gunman walked up and started shooting, police said.
A 25-year-old was shot in the abdomen and leg. The other man, 24, suffered gunshot wounds to the groin and leg.
They were both taken by paramedics to Stroger Hospital where they were listed in critical condition, police said.
No one is in custody as Area Four detectives investigate.