People are being robbed while doing chores such as cutting the grass and gardening.
Police say the same one or two men may be responsible for at least 11 robberies, many of them targeting senior citizens.
In addition to homeowners, landscapers doing work in the area are also being targeted in the Chatham neighborhood. The most recent robbery took place in the 8200-block of South Wabash. An 85-year-old man was robbed while watering his lawn.
Friday, on the 8200-block of South Wabash, there was outrage.
"He didn't deserve it. When I heard the news, I was mad. Very mad," said landscaping contractor Charles Boyd.
It was around 1 p.m. Thursday afternoon that police say the 85-year-old victim , while watering his lawn, was confronted by an armed man demanding money.
Investigators say, when the resident refused, a scuffle broke out, and the gun discharged, wounding the homeowner in the thigh.
"It's devastating to me in such a nice neighborhood, and it's a wonderful neighborhood, great neighbors over here, that some punk would just want to go over there and shoot this man," said 6th Ward Alderman Roderick Sawyer.
Before the suspect fled, police say the wounded homeowner, who is a retired law enforcement officer, managed to punch the shooter in the face.
"He's a very feisty guy, and he's always out here," said neighbor Darwin Honore. "He's kind of what we call 'the sentinel' in the neighborhood, because he's always standing on the corner. Everyone knows him."
Police say this isn't the first time the suspect has targeted a senior in his yard.
Detectives are investigating nearly a dozen similar incidents, all occurring in the past three weeks, within a square mile radius of Thursday's shooting.
"They target seniors because they feel they're an easy target. They're likely to put up less resistance. They're going to surrender property," said Chicago Police Sergeant Timothy Koren.
"We've had garage break-ins, burglaries, people have been attacked coming in and out of their homes," said neighbor John Johnson.
In addition to seniors, police say the suspect has targeted landscapers and contractors.
Charles Boyd says a man tried to rob him two weeks ago. Since then, he and his partner have been extra vigilant.
"We're sticking together. We're not separating. He's not going in the back. I'm not going in the front. I'm not going to stand out here by myself," said Boyd.
"Don't stop what you're doing. Let a trusted neighbor know that you're going to be out doing yard work. Have your neighbors around you keeping tabs on you," said Koren.
Police have only a vague description of the suspect, who is believed to be in his 20s. The suspect ran to a nearby gas station where another man was waiting in a blue or black four-door Pontiac Grand Prix.
Call Area 2 police if you have any information leading to that vehicle or a suspect.