Police say the victims were standing in a parking lot in the 7100 block of North Clark Street around 1:30 a.m. when they were shot at.
A 37-year-old man was dropped off at St. Francis with gunshot wounds to the chest and was pronounced dead.
A 36-year-old man was also taken to St. Francis in critical condition with gunshot wounds to the abdomen and back.
There is no one in custody. Area Three detectives are investigating.