Once we could fly airplanes, was it so much of a leap to imagine flying your house from place to place instead of getting into a plane to take you there? It would be much more convenient to just take literally everything with you to visit family, instead of figuring out how you're going to cram everything into a suitcase. But we don't even have a flying car yet -- a vehicle capable of both driving on roads and taking to the sky -- and scientists have been working on one of those for nearly 100 years.
Nor does everyone have a personal aircraft for getting around. Several "home of the future" models from the 1950s and 1960s featured hangars or even landing pads, anticipating flying as being our primary mode of transportation in the future. It made sense at the time that the cost of personal aircraft would go down, and the public did not anticipate the cost of fuel or the difficulty in creating "skyways" across the country. But let's think about the practicalities of having a flying house. Does it mean literally getting a typical house, which isn't even remotely shaped for air flight, up in the air? What about the costs of the fuel required to boost and propel that much weight? We aren't even nearly there.
The closest you can come right now to a flying house is a luxury private or chartered jet. They can have huge, plush seats and comfy beds, wooden furniture, large spa-like bathrooms, and kitchens (some even equipped with private chefs). Not the same as traveling in your own home, but far better than squeezing into coach class on a red-eye flight. Unfortunately, those comfy, anytime-you-need-them jets come with a high price, so for now you'll need to keep booking those flights.