Chicago police said the first two robberies are connected, but are still determining if the third incident was by the same suspects.
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The first incident happened in Streeterville, where a 26-year-old man was walking with a 23-year-old woman in the 400-block of East Ohio Street at about 11:40 p.m. The couple, originally from Oak Park, were out enjoying a walk to end their date night, and were less than half a block away from where they were parked when they saw a white car driving the wrong way down the street towards them.
The couple spoke to ABC7 over the phone, and asked to remain anonymous for their safety.
"Three or four people halfway out of the car. They pointed guns at us and said, 'Give me everything now,'" the woman said. "I just kept repeating to them, like, we're poor. We have nothing, which we are. We like, we had $15 to our name. Everything happened in, like, less than 30 seconds and I was completely in shock."
She didn't realize until she called 911 that her boyfriend had been pistol whipped.
"I just saw him spitting blood and I was just, I had it," she said.
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The man had his wallet and phone taken at gunpoint. Doctors told him his jaw is fractured in multiple places, and he now needs emergency surgery.
"We can't afford a surgery and the recovery that it's going to be," his girlfriend said. "We can't afford to get a new phone for him, and he needs his phone for work. It's just, I'm just scared."
The victims said the robbers were in their teens to early 20s, and had hoodies and masks on.
About an hour after the Streeterville attack, around 12:30 a.m. in Lincoln Park, a victim was standing on the sidewalk in front of a restaurant in the 1700-block of North Clybourn Avenue at about 12:30 a.m. when police said five male suspects got out of a white sedan.
The group took the victim's phone and wallet at gunpoint and fled the scene, police said.
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Police are investigating whether a third armed robbery in Wicker Park is also connected to the other two armed robberies.
Chicago police said at about 12:50 a.m., a 34-year-old man was standing on the sidewalk in the 1800-block of West Division Street when police said three male suspects got out of a white sedan.
The suspects took the man's phone at gunpoint and fled.
No arrests have been made in any of these incidents. Investigations by Chicago police are ongoing.