All of the incidents happened in North and Northwest Side neighborhoods since last Friday.
Police say three suspects have pointed guns at people who were in their garages or alleys behind their homes. They then robbed them of money, wallets and cell phones and took off.
No one has been hurt.
Kathleen Frawley lives on the 2200 block of West Medill where police say someone was robbed at gunpoint, right under newly city-installed motion sensitive lights, last Friday evening. It happened moments after a strong-arm robbery in the adjacent alley behind the 2200 block of West Fullerton.
"The neighborhood is great. There are good people and families. There is always people walking around, so I would just say keep your eyes and ears alert and just watch out for one another," said Frawley.
"I'm from the 'burbs so I have a lookout in the city when I park. I try to make sure I'm aware of my surroundings. I can't say that for everyone. Maybe they are targeting people that may be coming home after coming home from the bars and easy pickings, so to speak," said Marco Zapata, area resident.
The Kennedy Expressway is just 300 yards over to the east, perhaps offering the criminals what they think is a quick getaway. It's a setup not unlike the area around the 3900 block of North Troy, where a motorist was robbed in an alley as they arrived home on Sunday at 4:55pm.
Twenty minutes later someone got strong armed for their wallet and cell phone just around the corner on the 3700 block of West Montrose.
Jill Marowitz, an ad writer and mother of two, chooses to live in the city.
"I lived in the city my whole life. I'm not surprised. I'm not comfortable with the fact that it's happening so close and so frequently," said Marowitz. "We're not scared people but we take precautions."
In all, there have been seven alley robberies. Sunday also saw incidents on the 6200 block of North Leona, 2400 block of North Maplewood and 2100 block of North Monitor -- all between 6 and 9 pm.
The police will only describe the offenders as three black men, 20-35 years old, 5'7" to 6'2" weighing 160-190pounds, with different baseball caps. At least one suspect had a gun. There has also been a description of a grey car -- possibly a Nissan Pathfinder -- that might be involved in the incidents.