The most recent robbery happened Tuesday night, when a person with a knife confronted two University of Chicago students.
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Some residents in the Hyde Park neighborhood are on edge after the robberies.
"I think me and other students hear about it from the school's emails," said University of Chicago student Tim Mei. "I think all of us are definitely a little bit concerned."
Chicago police have yet to confirm if the same suspect committed the crimes, a community alert was issued Wednesday to warn the community around the university.
"It's nerve racking, but I don't necessarily walk out when its super late, so I'm not nervous, but I do try to keep my guard up," said University of Chicago student Ledya Wreden.
The first incident happened around 10:30 p.m. Oct. 2 near 56th Street and Kenwood Avenue.
A few days later, armed robbers struck again just after 11 p.m. Oct. 6 in the 5400 block of South University Avenue.
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At least three more robberies happened in less than two hours on Oct. 14.
"I think I'll be a little less confident about walking around at weird hours by myself," said University of Chicago student Adam Light.
In each instance, two to five male offenders exited a vehicle and approached the victims who were walking, investigators said. The robbers pulled out a gun a demanded the victims' wallets, cellphones and phone passcodes before getting back in a car and driving away.
"That bit of weariness goes away, said University of Chicago student Ryen Williams. "Everywhere you go, you have to look behind your back a little bit."
Police continue to investigate and search for suspects.