When I lived in Chicago, a number of people commuted from Wisconsin in their own private planes. Not every day but perhaps flying back and forth twice a week. I think they lived in communities with private landing strips and then had private hangars in the airport in Chicago.
I found a neighborhood near Huntsville, Texas with a landing strip in the middle of it and each house had a hanger next to it. Strange, but whatever lifts your wings.
Prior to world war 2.0 lots and lots of folks commuted by air to downtown NYC and the financial district. Fuel rationing for the duration put an end to that sort of thing, and it never returned. A fair bit of helicopter commuting maybe.