Many of the vehicles were legally parked along the 1600 block of Indiana Avenue, while others were on 13th and 16th streets.
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A witness told police that at about 2 a.m., three male suspects got out of a black, four-door sedan and began to shatter the driver's side windows on about 20 to 25 vehicles.
"I don't know what they were looking for. Maybe just some quick cash, or maybe somebody had some jewelry hanging out," said Henry Melton, whose SUV was vandalized.
Raquel Mireles woke up to go to work to find her car with the driver side window smashed, but nothing was taken.
Last year her car was stolen down the street. Her eyes were filled with tears.
"I mentioned it's kind of an inconvenience, but it's like more than that because you just feel like you know violated like your things are going through and it's just super frustrating," she said.
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Others were on 13th and 16th streets. Raven Pierce's red Genesis was hit.
Raven Pierce discovered her car had been damaged on 13th Street near Indiana Avenue.
"I came out here and I looked around and it's just glass everywhere and I'm just like, 'what?'" Pierce said. "It's just frustrating because people are constantly doing this around here now. It's been so many cars missing, cars broken into on a constant basis and you would think that your own stuff is safe in your neighborhood, but apparently not."
Neighbors said things like this happen constantly in the South Loop. Many have considered leaving or digging deep to put their cars in pricey garages.
Ronnie Ata found his car smashed and burglarized, but he's trying to stay positive.
"Honestly I'm not too surprised," Ata said. "It's the second time it's happened so I guess I'm not gonna cry over spilled milk. Like I said, I have a lot to be thankful for. It is a difficult area but I'm not really gonna let it get to me."
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Alderwoman Pat Dowell said this is disheartening.
She said this is the second time in less than a week that cars have been vandalized in the South Loop. Alderwoman Dowell said she is requesting that CDOT increase lighting in this area.
SEE ALSO: 3 injured, at least 6 parked cars damaged in Skokie crash on Karlov Avenue
No one is in custody, police said.
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