It hit central Illinois and parts of Indiana, where there were tornado watches and thunderstorm warnings.
Hail fell in Lafayette, Indiana. Some roads were covered in several inches of water.
Building debris was also left piled up on the streets of a southern Indiana town's courthouse square.
The National Weather Service says Monday night's storm damaged numerous buildings in the Orange County town of Paoli, about 40 miles northwest of Louisville, Ky. The town also had widespread power outages following the storm, but no injuries were immediately reported.
WAVE-TV reports that the building for the town's police and fire departments was among those damaged and that several homes and businesses had roofs torn off.
The Times-Mail of Bedford reports much of the town's power is back on Tuesday morning, although the opening of schools was delayed.
The Associated Press contributed to this report.