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When one checks in online, Delta now asks how much money in travel vouchers it would take to get you to voluntarily give up your seat and be bumped to another flight. Suppose what I'd really like isn't travel vouchers but rather an upgrade to first class. Is it possible to request something like that? Even better, is it possible to say, I'll take either $X + an upgrade or $X + $Y?

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    You can offer whatever you want, and they can accept or reject your offer regardless ;). – B.Liu Oct 29 '18 at 20:24
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    The airline will normally fill first class by upgrading frequent fliers. If they have seats available and haven't yet upgraded you, they probably haven't yet reached the point where the compensation for economy fliers is more costly than upgrading them. But you can always ask. – phoog Oct 29 '18 at 21:45
  • @bliu how do I make that offer. There's no button for "upgrade" on the bidding page. – Daniel Oct 29 '18 at 23:48
  • @Daniel Apologies, I assumed the person in question is already at the counter having access to a physical person. That would be a totally different question. – B.Liu Oct 30 '18 at 7:30
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    @phoog I think the OP means to get a first class seat on a later flight instead of an economy seat plus vouchers. I know most airlines can put you into premium economy. – user71659 Oct 30 '18 at 21:22
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There's currently no standard way to request that a portion of your compensation be a first class seat on the new flight you're bumped to.

My speculation is: requesting this would involve talking to the agent at the gate inside the airport while they find you a new flight. At that point you could offer to upgrade to first class if a seat is available. Doing this beforehand online is hard since the airline doesn't know which new flight you will agree to.

If you mean you want to be placed in first class on your current flight instead of being bumped to another flight, I believe that can't happen because your current flight is already 100% full.

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    I believe the question is describing a situation where you volunteer to be bumped from one flight in exchange for an upgrade on the next flight. In other words "I'll give up my seat on the noon flight in exchange for first class on the 4pm flight." In that case, the 4pm flight wouldn't be full, and it's possible that there's still room in first there. It sounds like you're describing a situation where someone volunteers for an upgrade on the same flight, which, sure, everyone would want that. – Zach Lipton May 16 at 20:09
  • I believe you're correct... I updated my answer to reflect that. – Christopher Pratt May 16 at 21:24
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    I have done exactly this. Once I got upgraded to first class, once to Premium Economy, and several times no upgrade at all. – Andrew Lazarus May 16 at 22:53

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