edit: ON BUDGET AIRLINES 
20 hours one-way to flyover country 
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My dad is the master of picking out the worst possible flights he can so he and my brother are flying out at 6am the day after Christmas. We're staying at my grandmothers place who lives an hour an away from the airport. And my dad is one of those types that wants to be at the airport two hours early just in case something goes wrong. It's a wildly stupid situation that's 100% self inflicted.
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Have you confronted him about it? You may as well stay up all night with that itinerary.
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I just don't fly with him ever or leave close to the same time which isn't that hard since we live in different cities.
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Not flying with family is a good practice in general
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That better be 2 hours before the recommended arrival time and not 2 hours before takeoff
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