The first break-in happened at about 4:29 a.m. at InnJoy Logan Square Bar on Milwaukee Avenue, Chicago police said.
CPD said four suspects broke the front glass door of the business and stole cash.
Video captured by ABC7 showed a safe near the sidewalk of the bar.
The suspects fled southbound in black sedan, police said.
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About 20 minutes later, police said suspects in a dark-colored Jeep SUV crashed into Arturo's Tacos at Western and Armitage.
ABC7 captured as police investigated the scene. Police said the suspect vehicle was left behind.
On the South Side, police said four small businesses were also victim to burglaries and damage on Monday.
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