There are
924 mi
from Waukegan, IL to Middletown, CT
That's the driving distance. It would take 17 hours 26 mins to go from Waukegan, Illinois to Middletown, Connecticut.
The flight distance (direct flight from Waukegan, IL to Middletown, CT) is 781.53 mi.
924 mi = 1,487.14 kms