Typically you can't book a connecting flight without at least 45 minutes to an hour of layover in between. So you've got that delay, then the flight (and any associated delays) then the whole "get off the plane and wait for your luggage deal", then more time while you try to get out of the airport, rent a car, etc.

And also something to consider is limited flight availability in small airports. I just had to spend three hours stuck in the Flint, Michigan airport because there were only two flights a day to Detroit. I could have driven to Detroit in less time than that and gotten an earlier flight home.

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