The driver was taken to Advocate Christ Hospital in Oak Lawn where he was listed in serious condition.
The driver had pulled to the corner of 65th and Hermitage to buy a drink at a store. He was approached by two men.
"My understanding is he was confronted when he was in his truck stopped, while he was getting out to go to the store," said Cmdr. Leo Schmitz, Chicago Police Department.
The driver was shot once in the back. The shooters fled on foot.
"I heard a big boom, looked out of my window and I noticed there was a man laying on the ground, and there was a couple people around him telling him to stay still, don't move. Me and my son walked up to him. He was shot in the back. He was stable. He was talking the whole time," said Priscilla McMiller, neighbor.
Witnesses say gunshots and robberies are common in the area.
"(Delivery drivers) get stuck up all the time. It doesn't make no sense. These people are making an honest living," said McMiller.
Police spent much of the day going door-to-door trying to get information from neighbors. Police are hopeful to get some cooperation in the neighborhood to help solve crime.
At the 7th District police station, a mother who lives on South Hermitage said her 19-year-old son was taken into police custody and her house was searched. She added her 19-year-old son had absolutely nothing to do with the shooting.
Investigators say they are questioning several people but have not made any arrests.
A spokesperson for UPS says they will continue to deliver to the Englewood area and they do have security measures in place for all drivers. They would not go into detail about the measures.
UPS says the driver has been with the company since 1997 and a regular driver since 2003.