There are
2,683 mi
from Upland, CA to Chesapeake, VA
That's the driving distance. It would take 1 day 23 hours to go from Upland, California to Chesapeake, Virginia.
The flight distance (direct flight from Upland, CA to Chesapeake, VA) is 2,317.73 mi.
2,683 mi = 4,317.46 kms