Anything before 09/11/2001.
Southwest.
Because I’m terrible at being on time and it’s nice to know I can just cancel as long as they haven’t taken off and not lost the money. Also not paying extra for luggage. And their airport is best for my parents place.
Joke answer: I once got to fly on a private jet. It was pretty frickin sweet. Show up to the FBO ten minutes before departure time. Pilot haphazardly wands us. Cabin seats 8, and all 8 of us work for the teapot factory. Plane was owned by the factory’s owner.
Real answer: I flew United a couple times last fall and had great experiences. Last time before that was flying Southwest back in 2018, which was also a fairly good experience.
American has actually done alright by me for the most part, though I hate every single thing about air travel except the actual act of soaring above the clouds in a metal tube that’s belching face-meltingly hot blasts of compressed gasses. That’s actually kind of awesome.
I live right by AA’s HQ and main hub though, and DFW is an underrated airport, especially as your “home base” where you don’t need to manage connections.
USAF. No TSA checks, no baggage restrictions, you can visit the cockpit and you can hang a hammock in the back
It made me realize my problems with flying revolved around airports, not so much the airlines themselves.
USAF C130 between Kuwait & Iraq was a weird experience. On the way out, it was “aw shit how many more months do I have?” On the way back it was “how much longer until I can get a beer?” Plane was fine while in air, but lowering the ramp on either end felt like walking into a damn blast furnace.