The 53-year-old was arguing with another male around 12:27 a.m. in the 5800 block of West Madison Street when they both pulled out handguns and exchanged gunfire, police said.
The 53-year-old was struck multiple times in the torso and was transported to Stroger Hospital where he was pronounced dead, officials said. He has not yet been identified by the Cook County medical examiner's office.
The other gunman fled the scene on foot.
A 23-year-old man who was nearby suffered two gunshot wounds to the back, police said. He was taken to Mount Sinai Hospital in fair condition.
A 42-year-old woman was also outside during the shooting and was struck by gunfire in the arm, police said. She was taken to Stroger Hospital where she was listed in fair condition.
No one is in custody as Area Four detectives investigate.