There are
905 mi
from Chesapeake, VA to Wauconda, IL
That's the driving distance. It would take 17 hours 42 mins to go from Chesapeake, Virginia to Wauconda, Illinois.
The flight distance (direct flight from Chesapeake, VA to Wauconda, IL) is 735.87 mi.
905 mi = 1,456.37 kms