There are
2,235 mi
from Waukegan, IL to Roseburg, OR
That's the driving distance. It would take 1 day 16 hours to go from Waukegan, Illinois to Roseburg, Oregon.
The flight distance (direct flight from Waukegan, IL to Roseburg, OR) is 1,787.23 mi.
2,235 mi = 3.22 kms