There are
923 mi
from Waukegan, IL to Rutland, VT
That's the driving distance. It would take 18 hours 10 mins to go from Waukegan, Illinois to Rutland, Vermont.
The flight distance (direct flight from Waukegan, IL to Rutland, VT) is 755.57 mi.
923 mi = 1,486.21 kms