There are
986 mi
from Bridgeport, CT to Sheboygan, WI
That's the driving distance. It would take 18 hours 44 mins to go from Bridgeport, Connecticut to Sheboygan, Wisconsin.
The flight distance (direct flight from Bridgeport, CT to Sheboygan, WI) is 759.82 mi.
986 mi = 1,587.45 kms