Dictionary.com dates the expression "flying blind" to World War II, but of course it's as old as aviation and frequently appears in print during World War I. For example, there's this from the Irish Times: "The pilots, flying blind through the clouds" (Oct. 9, 1918).
Today's owl with a paper bag over its head flying blind into a jack-o'-lantern house is from We Can Read Magic and Make-believe Book Two by Gerrard & McInnes, 1965.