Once I flew to a city that's about 6 hours away by car. Work was paying for it, and I figured it would be easier and less stressful to fly than to drive. A coworker drove instead. He left 2 hours after I left for the airport. After my plane arrived they were cleaning it out and one of the attendants hit his head and had to go to the hospital for stitches. I scrambled and was able to get on to another flight, although it took me about 2 hours into the opposite direction, where I then had to sprint from one end of the airport to the other. When I finally landed in my destination city my coworker had been there for over an hour. There was nothing easier or less stressful about that day.

That said, that was my worst experience flying, usually it is very easy - especially if I'm traveling by myself.