There are
2,160 mi
from San Mateo, CA to Winnetka, IL
That's the driving distance. It would take 1 day 13 hours to go from San Mateo, California to Winnetka, Illinois.
The flight distance (direct flight from San Mateo, CA to Winnetka, IL) is 1,848.91 mi.
2,160 mi = 3.22 kms