One victim is known to the people on his route as Mr. Bob; he's been doing this since 1979, and told ABC7 this was the scariest moment he's ever had on the job.
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USPS said the two robberies took place less than a mile apart from each other.
"It's a great concern for our letter carriers, for their safety," said Elise Foster, USPS. "NO one should have to work and be in fear of their lives while performing their duties at work."
The incident involving Mr. Bob unfolded in the parking lot of a community assistance organization near 117th and Halsted. Employees witnessed the entire incident, but asked to remain anonymous.
RELATED: Chicago USPS mail carrier recounts terrifying armed robbery in Humboldt Park
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"We saw a car pull up really quickly very close to the mail truck and he jumps out of the car, walks quickly over to the truck and he's doing something we can't see but he's moving fast," one employee said.
Police said the 68-year-old mail carrier was held at gunpoint while the suspect demanded his property before driving off in a dark-colored SUV. He was not physically harmed, but was shaken up.
"It was very scary," the employee said. "This is not something that's normal. We don't usually see this type of activity, not over here."
MORE: Armed robber targeting Chicago postal carriers for master keys, police warn
A female postal worker was also robbed at gunpoint just after 11 a.m. in the 400-block of 117th Street, less than a mile away.
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"She was just delivering mail and someone asked her a question," Foster said. "She thought it was a friendly conversation."
That suspect also got away in a dark-colored SUV.
A USPS union representative said keys and equipment are the common targets of all the recent robberies.
As postal workers call on the city to provide more patrols and surveillance to keep them safe, others are hoping the solutions come from community resources.
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