There are
409 mi
from Waukegan, IL to Hopkinsville, KY
That's the driving distance. It would take 8 hours 46 mins to go from Waukegan, Illinois to Hopkinsville, Kentucky.
The flight distance (direct flight from Waukegan, IL to Hopkinsville, KY) is 380.35 mi.
409 mi = 657.99 kms