There are
845 mi
from Oswego, IL to Poughkeepsie, NY
That's the driving distance. It would take 16 hours 5 mins to go from Oswego, Illinois to Poughkeepsie, New York.
The flight distance (direct flight from Oswego, IL to Poughkeepsie, NY) is 743.66 mi.
845 mi = 1,359.23 kms