I usually fly with Singapore Airlines. The service is always exceptional. One time (out of about a dozen trips) the flight was cancelled due to engine issues. After explaining I had a conference to attend and the next flight would mean missing one out of three days, they booked me an United ticket and offered me some points as an apology for the "inferior service". It was.
IIRC, in the US, airlines are required by law to book you on the next available flight on any airline. Of course, they prefer to keep you on their own planes, and it is probably impractical to move every single passenger, anyway, so you do have to ask.
In the EU there are similar laws. Compensations start as soon as a plane is delayed by more than two hours. My dad has gotten quite a substantial chunk of money back on a regular vacation ticket after it was delayed for a few hours.
You have to ask, but I have noticed in recent years that they're quite open about the fact that the program exists, with posters all over most airports.
On the flipside, I think there is a sort of loophole that some cheap EU airlines use, where if all the passengers board the plane, they can keep you delayed (and boarded) for a few hours with no compensation. I've been stuck outbound from Gatwick, sitting in the plane for 2.5 hours with no food and no compensation, due to illness causing shortage in the flight attendant staff. I believe they knew about the delay before they boarded us.
I'm confused by this. EU passenger rights http://europa.eu/youreurope/citizens/travel/passenger-rights... also apply to planes that arrive late. Hence, if they make you board the plane and wait, presumably you will also arrive late, and be entitled to a compensation.
I suppose the difference is that you're more likely to claim compensation whilst you've got nothing better to do than waiting to get on a plane in a terminal full of posters telling you to claim that compensation than once you've actually made it to wherever you're going.
Weather delays must not count. I've had a mechanical failure turn into a weather delay. We get a free hotel room the first night of the delay, but slept in the airport the rest of the delay because it was "due to weather."
I'm not sure what the conditions are, but the airlines are required to do that by law under certain circumstances. Maybe someone more knowledgable could chime in?
For flights to/from EU member countries, Regulation 261/2004 is applicable. I guess Rule 240 would be the US equivalent.
It can be tricky to get the airline to comply when they deny responsibility. So there are intermediary agencies that do the claim paperwork (and take the legal actions if necessary), taking a small percentage of the reward only if successful.
With the help of an intermediary, I successfully invoked Regulation 261/2004 against KLM after a flight was cancelled due to mechanical failure. The correct reward was ultimately transferred approximately one year after the original flight.
I got €400 compensation from Ukraine International Airways under the EU regulations after simply sending them a letter requesting it, after a 30 hour delay.
In the US, before deregulation FAA Rule 240 [1] covered this scenario. Now the specifics between airlines, but the place to look is the 'Conditions of Carriage' contract that each airline is required to abide by.
This Consumerist article [2] is out of date (2007), but it covers every airline's contract and I believe it remains mostly correct.