A clever testimonial on Money Crashers explains how the writer procured four free flights by buying tickets for potentially overbooked flights, then getting bumped and paid off in travel vouchers.
From the post:
If you volunteer for an overbooked flight, expect to wait around for a while before you receive your voucher. While the airline employee is truly grateful for your volunteering, their main focus will be to get other travelers on the plane on time. You will not receive your voucher or any detailed instructions until this is done.
When you volunteer, they will ask for your airline ticket and offer you another flight either later that day or the next day. If it is a next day flight they will offer you a hotel voucher as well. If they don’t mention this, make sure to check with them. Once you agree to a later flight, they will book you on that flight and return their attention to the boarding passengers. Take a seat near the information desk and wait until they call you. Do not wander off! Sometimes they’ll realize seats are available at the last minute. If that is the case, you are expected to board and should still get the compensation!
Seeing this sort of advice online is particular gratifying for me, given that I devoted a chapter to getting bumped from flights in Secrets of a Stingy Scoundrel.
What are your favorite cheapskate air travel techniques?