There are
816 mi
from Waukegan, IL to Middletown, NY
That's the driving distance. It would take 15 hours 15 mins to go from Waukegan, Illinois to Middletown, New York.
The flight distance (direct flight from Waukegan, IL to Middletown, NY) is 692.37 mi.
816 mi = 1,312.82 kms