There are
1,033 mi
from Waukegan, IL to Medford, MA
That's the driving distance. It would take 19 hours 41 mins to go from Waukegan, Illinois to Medford, Massachusetts.
The flight distance (direct flight from Waukegan, IL to Medford, MA) is 852.79 mi.
1,033 mi = 1.61 kms