A 33-year-old woman and a 35-year-old woman were standing outside in the 2000-block of West North Avenue just before 3:50 a.m., when two suspects pulled up in a vehicle and demanded their property at gunpoint, police said.
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The man tried to help, and was shot twice in the abdomen, police and fire officials said.
It's unclear if the three knew each other.
"It's scary and tragic that the person that was helping them is the one who fell victim to it," neighbor Hanna Weiss said.
The suspects drove away in a silver sedan, traveling west on North Avenue, police said.
Witnesses said they were dressed in black with ski masks covering their faces.
The man was taken to Stroger Hospital in critical condition.
"There's nowhere safe," neighbor Garren Garcialazo said. "It can happen here, there, anywhere."
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The three had been standing in front of Estelle's Café & Lounge, located at 2013 W. North Ave., CFD said.
Estelle's owner David Halpern issued a statement saying, "Our cameras did capture the entire horrific incident. Our prayers go out to the victim who was shot and the others who were robbed at gunpoint. We are enthusiastically cooperating with the police."
Chicago police had part of North Avenue near Milwaukee Avenue closed, while they investigated later Friday morning.
SEE ALSO: Chicago police investigating at least 6 overnight business break-ins, possible burglaries
It's a very busy part of the Wicker Park neighborhood.
Crime scene tape surrounded Estelle's and the alley next to it early Friday.
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Witnesses said at least one of the women ran into the bar after the shooting, and customers inside were seen taking cover.
"This is in close proximity, so it is concerning," neighbor Jason Goldberg said. "You never think something crazy like that's gonna pop off when you're walking out of a bar."
No other injuries were reported, and Area Five Detectives are investigating. No one was in custody later Friday.
Chicago police believe the same car may have been involved in several armed robberies Thursday morning.
They're hoping to find surveillance video in the area.
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