One of my parents use to be an executive for one of the major airlines in the world, and as part of his retirement contract my whole family can fly for free for the rest of our lives. This is not the usual airline benefit where it is a standby ticket, rather, we pay for the ticket with unlimited 'fake' money in the same process a normal customer would. Also, I have the status of their middle tier frequent flier program, so it appears to employees that I fly 75k miles every financial quarter. AMA
Edit - Inspired by the lotto winner of $30 mill AMA, he flys around the world cause he got lucky, I do it too! Also for the most part, I don't do this alone, I have a brother 5 years older than me who travels with me a good bit, and a small number of my friends also have 'standard' benefits and fly standby with me also, so we jetset around 2 or 3 times a year together.