Chicago police said they were first called to the 700 block of S. Financial Place at around 4:05 a.m. Officers found a damaged Mercedes-Benz and a Lexus at that location.
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Tattoo artist Alexander Velazquez found his car damaged.
"I don't think I'm going to continue to park here at all," Velazquez said. "I'm probably going to find another closed garage."
Velazquez said not only were his car windows busted, but two of his prized signed skateboards were stolen.
"I've heard some things about the area, but it's the first time I've seen kind of something like this happened in this parking lot," said Mohan Raval, whose car was fortunately found undamaged. "It is definitely concerning.'
Police said they found nine more damaged cars a block away, around 4:12 a.m. in the 600 block of South LaSalle at a parking garage located there. Video showed the vehicles had been ransacked with items left on the ground.
A woman who did not want to be identified said hundreds of dollars in damage was done to her SUV. A side window was broken, a pair of old shoes were stolen, and her grocery bags were strewn on the ground.
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Less then ten minutes later, officers were called back to the 700 block of S. Financial Place for another damaged Volvo.
Some neighbors said this isn't the first time vehicles in the neighborhood have been broken into, and they want to see more police patrols in the area.
"I used to feel safe walking around here in the evening," South Loop resident Janice Morris said. "I don't any more, so I would like to see a more visible police presence around here."
Chicago police have yet to confirm if the latest rash of vehicle break-ins are related to any others in the neighborhood.
No one was in custody as detectives continue to investigate.