There are
2,095 mi
from Waukegan, IL to Milwaukie, OR
That's the driving distance. It would take 1 day 12 hours to go from Waukegan, Illinois to Milwaukie, Oregon.
The flight distance (direct flight from Waukegan, IL to Milwaukie, OR) is 1,731.43 mi.
2,095 mi = 3.22 kms