There are
2,099 mi
from Waukegan, IL to Lake Oswego, OR
That's the driving distance. It would take 1 day 12 hours to go from Waukegan, Illinois to Lake Oswego, Oregon.
The flight distance (direct flight from Waukegan, IL to Lake Oswego, OR) is 1,733.15 mi.
2,099 mi = 3.22 kms