There are
853 mi
from Waukegan, IL to Poughkeepsie, NY
That's the driving distance. It would take 16 hours 4 mins to go from Waukegan, Illinois to Poughkeepsie, New York.
The flight distance (direct flight from Waukegan, IL to Poughkeepsie, NY) is 715.24 mi.
853 mi = 1,372.82 kms