There are
435 mi
from Chesapeake, VA to Poughkeepsie, NY
That's the driving distance. It would take 9 hours 22 mins to go from Chesapeake, Virginia to Poughkeepsie, New York.
The flight distance (direct flight from Chesapeake, VA to Poughkeepsie, NY) is 363.51 mi.
435 mi = 699.92 kms