There are
1,989 mi
from Upland, CA to Winnetka, IL
That's the driving distance. It would take 1 day 10 hours to go from Upland, California to Winnetka, Illinois.
The flight distance (direct flight from Upland, CA to Winnetka, IL) is 1,707.56 mi.
1,989 mi = 1.61 kms