How to make money traveling

It's true, my older brother and several friends set off on vacation to try and recoup some of their money.  How?  They try to get bumped by the airlines and all have been successful to varying degrees. 

It makes sense to both parties. 
Think of it from my brother's point of view; he and his wife have two boys they travel with.  4 adult tickets whenever they go anywhere.  Even if they only net $300 each for being bumped, they receive $1200 total.  Think of it from the airlines' point of view; they get to bump 4 people at once, and only create one set of paperwork for the entire transaction.  It's good for both parties. 

Huh?
My brother is the one that turned me on to this form of traveling.  When he was attending grad school he'd fly to our mother's house for Christmas vacation. One year he arrived 4 hours later than planned and $600 in airline money richer.  He volunteered to be bumped from his flight to a later one and, since he was traveling Christmas Eve the amount was higher than usual.  $600 to a grad student, not bad.

Or...
Once I was on an American Airlines flight that connected in Miami to Turks And Caicos.  Short story, we missed our connection via American by ten minutes, but it was their fault.  So we asked for, and received, an upgrade to First class for the remainder of the flight and $400 in travel vouchers.  I love American Airlines because of their service to the Caribbean, so the travel vouchers were great, and I always ask for first class. 

And...
Returning to California one year via Miami I was on another full flight and they asked for volunteers.  When I got to the podium they were offering $350 and a guaranteed seat on the flight leaving in 2 hours.  When it was my turn to put my name on the list I said I'd accept, if they bumped me to first class.  Turns out they needed my seat and they had the room in First Class on the next flight, so I got my wish.  But wait, there's more.  The next flight was also very booked, and this time there were less volunteers to be bumped.  It was later in he day and direct flights to LA were running full and scarce.  At the end of the day I received close to $1,000 and a connecting flight in First Class all the way home.  Because I was flexible to do so.

How do I do that?
Here are some tips we've collected about this excellent way of upgrading your travel, or adding free travel to your schedule.

1. Be nice.  A ticket agent during the holidays spends a lot of time staring at angry faces and upset customers.  If you're the one nice person in their field of vision it can go a long to helping you get what you want. 

2. Be flexible in your travel plans.  Usually people try to get bumped on the way back from vacation.  But there are also people that like to make stops on the way.

3. Ask for it.  Whenever you're talking to a gate agent or ticketing person ask them if the flight is oversold and might be bumping people.  If they haven't announced it yet you might get first chance, or at least be at the top of the list of people.

4. Ask what the airline is offering.  Airlines used to offer free round trip tickets which was excellent.  Now they've taken to offering a set amount of money.  The amount depends on too many factors to note here, but usually starts at $150 and goes up from there. 

5. Ask what else it includes.  When we got bumped in Miami we also talked them into an upgraded suite for the overnight stay, dinner vouchers, and of course a free ride to the hotel.  It was a great night in Miami.  We were already planning to be in the Caribbean for 14 nights, and we had an excellent night in Miami.

6. Stay close to the podium.  Closest one wins in some cases, so when they call people, be there.

7. Be nice.  It can't be emphasized enough.  Sometimes airline employees have to make spur of the moment decisions to keep the flights running along smoothly, and if they have to choose someone to receive $500 and you're in their field of vision and were nice, it might just seal the deal.  The first time I got bumped out of Los Angeles the ticket agent just happened to be the brother of a professional contact I knew.  I flew 2,200 miles in First Class that flight. 

Good luck.  And please, write us and tell us if you've had any similar experiences.