Some of the incidents were captured on surveillance video. In each, the suspect was reported breaking into the bar by breaking a window.
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Five bars - Cobra Lounge & All Rise Brewing Company, Hurley Tap, Lottie's Pub, Tuman's Tap and Grill, and The Irish Nobleman - all reported similar break-ins by at least one person within a matter of hours Tuesday.
Three of the five bars shared images and video captured from the Tuesday morning crimes.
The owner of Hurley Tap off Cortland and Paulina in Wicker Park, said just before 3 a.m. Tuesday, someone broke a window and ransacked the business before taking off with two iPads.
Less than an hour later, at 3:41 a.m., Cobra Lounge & All Rise Brewing Company off Ashland and Fulton reported a similar break-in.
"We have three bars within the building and he went behind two of them and stole the cash boxes attached to the point-of-sale's system," said general manager Louie Mendicino. "He walked directly behind the tap room bar, knocked over the point-of-sale system, ripped out the cash drawer and then he made his way around to front bar. Did the same thing there and left out the side door."
Half an hour after that, at 4:10 a.m. there was another break-in at the Irish Nobleman Pub at Erie and Noble in West Town.
"We saw the guy running out the window and he was probably in here for about five minutes and then a couple minutes later police showed up," said Declan Morgan, owner.
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Morgan said after getting an alert, his wife yelled at the suspect through their security system.
"He just stopped dead and my wife said, 'get the hell out.' And he literally ran and jumped out the window," Morgan said.
The mess left behind from all the crimes did not deter the neighborhood hangouts.
"We've been around for 17 years, we're an institution in the neighborhood, and we're not going anywhere," Mendicino said.
"We've been here for over 20 years, we hope to be here another 20 years," Morgan said.
Chicago police said so far no one is in custody for any of these break-ins.