There are
2,095 mi
from Naperville, IL to Milwaukie, OR
That's the driving distance. It would take 1 day 12 hours to go from Naperville, Illinois to Milwaukie, Oregon.
The flight distance (direct flight from Naperville, IL to Milwaukie, OR) is 1,730.22 mi.
2,095 mi = 3.22 kms