Several 911 calls came in just after 12:30 p.m. for a report of a plane crash in a field behind a business at 260 W. Lincoln Highway in Cortland, the sheriff's office said.
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Cortland police and the sheriff's office found the plane.
Two men were inside, and suffered unknown injuries, police said.
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They were taken to Northwestern Kishwaukee Hospital in DeKalb.
The Federal Aviation Administration and National Transportation Safety Board will investigate.
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Chopper 7 was over the aircraft about 1:30 p.m. The small plane appeared to have front-end damage, and a fire truck had responded to spray foam on it.
According to FlightAware, the plane departed from Evansville Regional Airport in Indiana about 10:10 a.m. It was supposed to land at DeKalb Taylor Municipal Airport just after 12:30 p.m.
It appeared to have crashed just south of the DeKalb airport.