There are
364 mi
from Waukegan, IL to Shelbyville, KY
That's the driving distance. It would take 7 hours 7 mins to go from Waukegan, Illinois to Shelbyville, Kentucky.
The flight distance (direct flight from Waukegan, IL to Shelbyville, KY) is 318.34 mi.
364 mi = 586.44 kms