There are
885 mi
from Chesapeake, VA to Winnetka, IL
That's the driving distance. It would take 17 hours 6 mins to go from Chesapeake, Virginia to Winnetka, Illinois.
The flight distance (direct flight from Chesapeake, VA to Winnetka, IL) is 712.75 mi.
885 mi = 1,424.91 kms