Three of the incidents happened on the city's South Side. One of the most recent incidents happened in broad daylight in Lincoln Park on the North Side.
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Police said the letter carrier was on his route in the 2500-block of North Ashland Avenue on Wednesday when he was robbed at gunpoint by two men at around 11:30 a.m.
They got away in a dark colored Kia sedan with tinted windows. Investigators released surveillance photos of the getaway car.
The U.S. Postal Inspection Service is offering a reward of up to $50,000 to anyone who can help police arrest and convict the offenders.
"It's just very unfortunate," Lincoln Park resident Nick Bledsoe said. "I mean it's sad. It's scary. There's a lot of families around here. Lotta good people."
Nearby resident Alex Fraser said mail and package crimes are becoming commonplace in the neighborhood.
"It never used to be the case but we've had people go into our building, dressed as Amazon workers and steal a bunch of packages dressed as postal workers and steal some packages," Fraser said.
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The head of the letter carriers union said that they are now working in fear.
"We want to deliver our letter carriers home to their families each and every day and they should not have to work in fear," Elise Foster, president of the National Association of Letter Carriers, Local Branch 11, said. "The letter carriers are out there performing their jobs, and then they're all of a sudden robbed at gunpoint. That's a very traumatic experience for anybody."
Illinois Senator Dick Durbin commented on violence against letter carriers Friday morning.
"Amazon has now discontinued truck deliveries in parts of the city of Chicago because it's too dangerous," Durbin said. "They leave the mail at the post office and say, you try to deliver what we normally deliver by truck."
"Amazon has pulled out and the postal workers are picking up the slack," Foster said. "But Amazon pulled out for safety concerns, so those safety concerns are now our safety concerns."
One postal carrier, who prefers to hide her identity, knows those safety concerns all to well. She was robbed at gunpoint in the fall. Traumatized, she's shocked this continues to happen.
"It's continuing to happen every day and we need some type of security," she said. "That's the only way they're going to stop doing it. Otherwise they're going to keep doing it."
Last Thursday police issued a community alert warning about the two incidents on the South Side at 117th and Halsted streets and 117th and Stewart. Then Thursday, another mail carrier was robbed in that same area near 107th and LaSalle streets.
"He kindly walked down the steps and told me, 'If I call the police, he was going to kill me.' He was going to come back on my route, find me and literally kill me," said one of the victims.
It's a lingering fear that has this letter carrier, concerned about showing her face as she recounts being robbed at gunpoint while on her delivery route.
She said her would-be attacker walked up the porch before finally making his intentions known.
"I was about to hand him the packages, thinking that he lived there because he was still standing there waiting," she said. "He let me scan the package and everything, standing there talking. And, I'm about to hand him the package and the mail, and then he looked at me and was like, 'This is a robbery. I need the key.' And showed me the gun. I was literally in a state of shock. I couldn't believe it."
The thief got away with her master key, driving off by himself in an SUV.
Police were soon called.
"I'm sitting in the police car, talking to them where they have to go right around the corner to another mail carrier who got robbed as they were taking care of me. I was like, 'Wow,'" the victim recalled.
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The U.S. Postal Service is asking the community to keep a protective eye on letter carriers. Terry Fuchow plans to do just that.
"I would say we should all look out for each other," Duchow said. "You know I think it's good mental health and it's just a good way for society to get along."
The letter carriers union said they are working with the postal service to get protection for the letter carriers.
"I'm terrified to even go back out there because if they don't catch you, I don't know if you live in that area. I deliver in that particular area so how would I know," one of the victims said.
ABC7 also reached out to Amazon, where a spokesperson said they are looking into details on whether any changes have been made to their delivery process.
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