One of the victims even hired an overnight security guard to try and prevent this from happening.
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For three days, thieves have been on a spree, targeting shops that sell expensive gym shoes.
A shoe store in the South Loop and another in the East Village neighborhood were both hit Thursday morning.
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Surveillance video captured the incident at the Boneyard Chicago at 1101 North Ashland Avenue.
After armed robbers threatened at gunpoint the security guard hired to watch the store overnight, the driver of a dark-colored Jeep Grand Cherokee then jumped the curb and rammed the storefront three times with the SUV before gaining entry.
At least eight people in hoodies broke into the store and robbed it.
"Nobody ever gets caught," store owner Jacob said. "They're using a stolen car. It is what it is, you know, but we're trying to avoid it from happening entirely."
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The Boneyard Chicago owner said after hearing about two other shoe stores that were targeted in the last two days, he hired a security guard to watch his store overnight. But that didn't deter the thieves.
"They pretty much surrounded him," Jacob said. "I want to say that's how it happened is that they surrounded him, pulled a gun on him. He pulled off and then that's when the Jeep came."
The owner of Boneyard Chicago said in the past he went as far as to install concrete barriers in front of his store, but the city removed them without notice.
"This would have never happened if the alderman did not come and take our barricades," Jacob said. "They wouldn't have been able to do this. They were blocking the store but now this is going to cost us."
Neither the 1st Ward alderman's office nor the Chicago Department of Transportation have officially commented yet on why the barriers were taken away.
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Boneyard Chicago is now making repairs to the store and hope to be fully reopened by the weekend.
This comes after two days of nearly identical crash and grabs.
At around 4:30 a.m., a group of thieves rammed a Jeep Cherokee into Unique Chicago on 18th and State streets in the South Loop, taking more high-end sneakers.
Wednesday, another shoe store was targeted in Little Italy, a Jeep Cherokee smashed into Flee Club. Surveillance video there showed the same type of burglary.
On Tuesday, a similar robbery occurred at a store in River North, where the thieves used two cars to smash into the store before fleeing in getaway vehicles.
No one has been injured in any of the robberies and no one is in custody.