The large tree slammed into homes on the city's South Side, and was still there Tuesday morning.
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Chicago home inspectors had to be called in to assess if the homes damaged were still structurally sound.
It happened late Monday night in the 1700-block of West 101st Street.
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The large tree snapped from strong winds and slammed onto a home, causing damage to not just one house, but the one next-door.
"It fell down, hit his house, took a big chunk out of the front, and it hit our roof. And we're going to need a new roof and some drywalling on the inside, but everybody's fine," said Steve Klinsky, whose home was damaged.
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A 48-year-old man was taken to Little Company of Mary hospital in good condition after the incident, CFD said.
City inspectors came out to take a look, and deemed the homes were sound enough to go back inside.
On Tuesday morning, homeowners will have to access any further damage in the daylight.
At least two brief EF-0 tornadoes touched down in the Chicago suburbs Monday morning, the National Weather Service said.