The fire started inside the pizza restaurant at the corner before spreading to two more business.
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One of them is a convenience store, Thorndale Mart, which has been in this neighborhood for decades. The owner, Ajay Shah, is left cleaning up the pieces while vowing to return.
"This is like my second home. And, working almost every day," Shah said. "So many fire trucks. That's the first time I've seen so many fire trucks at one place. Probably over 15, 20 fire trucks."
Shah has run the store for nearly 40 years.
"When I got in I said, 'Oh no.' I was sad," Shah said.
Chicago firefighters battled the blaze early Tuesday morning on Thorndale and Winthrop avenues, where smoke filled the streets.
Crews kept flames from reaching second-floor apartments.
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Authorities said the fire started inside of Rewire Pizza Cafe and Bar before spreading to two more businesses, gutting Shah's life's work.
"All that work done, and it's gone in five, 10 minutes, half an hour," Shah said.
He's now committed to seeing these store doors back open, hopefully, in the coming weeks.
"I know we will come back. You know, sometimes, it takes time to get it, but as long as we're alive, we can bring anything back," Shah said.
Chicago fire officials said no one was hurt. The cause of the fire is under investigation.