It happened Saturday night in the 1900-block of Lincoln Avenue where the man reportedly was trying to break into an apartment.
The man has been identified as Rickey Rozelle. Police say the 28-year-old convicted felon has a criminal record that is over 20 pages long and it includes over 50 arrests.
Rozelle was seen by the off duty officer at an apartment that was in the process of being renovated.
Some crime tape is still visible, a sign something went wrong in a Lincoln Park alley, something many in this neighborhood don't see or hear too often.
"This is in the cusp of Lincoln Park and Old Town, you kind of get the best of both worlds, you wouldn't expect this to happen," said resident Samy Elgazzar.
"I was coming back from a delivery as this was happening," said Jason Caruso. "I knew something was wrong. I didn't know this is what had happened."
What had happened was a man was shot to death by an off duty Chicago police officer. Police say the cop lives in the area and was returning home from work when he noticed a man with a flashlight trying to break into the 2nd floor apartment of this Lincoln Avenue building.
"The officer knows the apartment that he is standing at is vacant," said Pat Camden, Fraternal Order of Police spokesman. "He yells, 'What are you doing?' The guy shouts back, 'You don't want to mess with me.'"
Camden says the officer identified himself as a police officer and showed his badge. He talked the suspect into coming down stairs.
"He's carrying a backpack over his right hand and other tucked into waste of pants," Camden said. "Police officer tells him, 'Let me see your hands,'"
Camden says the offender refused to show the officer his hands as he walked into a dark gangway.
"At this point, the offender turns around and says, 'I'm going to kill you' and starts pulling hand from waste, officer fears for life and fires off two shots," he said.
Rozell was shot twice in the chest. It is has not been determined if Rozelle was carrying a weapon. The South Side resident has a lengthy criminal record that includes several burglaries.
Camden says at the time of the shooting, Roselle apparently had a backpack full of stolen items that included watches and phones. Rozelle's father said his son was a drifter with a past includes trouble with the law.
As in all police related shootings, Saturday night's is being investigated by the independent police review board.