There are
375 mi
from Waukegan, IL to Madisonville, KY
That's the driving distance. It would take 8 hours 9 mins to go from Waukegan, Illinois to Madisonville, Kentucky.
The flight distance (direct flight from Waukegan, IL to Madisonville, KY) is 348.40 mi.
375 mi = 603.63 kms