There are
2,044 mi
from Simi Valley, CA to Winnetka, IL
That's the driving distance. It would take 1 day 12 hours to go from Simi Valley, California to Winnetka, Illinois.
The flight distance (direct flight from Simi Valley, CA to Winnetka, IL) is 1,759.55 mi.
2,044 mi = 3.22 kms