Reader Ryan reached out to me and asked if I had any thoughts on how to book a flight for the same day that might be cancelled. I loved this question, because it’s exactly the kind of out of the box thinking that makes some travel hackers extremely successful.

Why did Ryan want to do this? The short answer is that airlines that cancel flights are, in most circumstances, obligated to give you a refund for a cancelled flight if you ask, and for other instances you can get a newly issued travel voucher with a new expiration date far out in the future. So, it’s a nice hack for extending an expiring voucher.

Finding Flights Likely To Be Cancelled

Over the 2021 holiday season, it seems like you’ve got about a one in five shot of having your flight cancelled without doing anything special, but normally that’s not the case. You can still tilt the odds in your favor though. To find flights that are likely to be cancelled:

  1. Check Flightaware’s misery map for the top three miserable airports
  2. Check the FAA’s national air status map for the top three airports experiencing traffic management issues
  3. Combine the above to come up with a route that passes through at least two of those airports, and even better a connecting flight in a third

When I looked for Ryan yesterday, Seattle (#1), Denver (#2), and Atlanta (#3) were having major issues, and Ryan’s expiring voucher was on Southwest. With Denver and Atlanta being Southwest hubs, I guessed the best option would have been either: SEA-DEN or DEN-ATL; but even better yet: SEA-ATL-DEN or SEA-DEN-ATL.

By the way, if you really want to tilt the odds in your favor, see where each individual flight is coming from on Flightaware and book one that’s already delayed or cancelled upstream. I didn’t do this yesterday though because I was in a hurry.

How’d That Work Out?

Let’s see how I did:

  • SEA-DEN: Southwest had six scheduled flights, none were cancelled, five were delayed
  • SEA-ATL: Turns out this route doesn’t exist
  • DEN-ATL: Southwest had four scheduled flights, none were cancelled, two were delayed

Ok, so I failed — but only a little:

  • SEA-DEN: All but one of the flights was delayed over an hour
  • DEN-ATL: Both delayed flights were over an hour delayed (or seemed to be as of this writing)

Alright, so if Ryan followed my advice, he’d still have a 5/6 shot of the first leg being delayed by at least an hour and a 1/2 shot of his second flight being delayed by at least an hour. There’s also decent chance misconnect in Denver. With an hour plus delay, calling Southwest is likely to get you at least a refund to a new travel voucher with a year later expiration, and it’s less likely but still possible that you could get a full refund. So, Ryan would have been in good shape even though we didn’t find the cancelled flight he was looking for.


If you have an expiring travel voucher, try and find a flight likely to be cancelled and book it. It could go well for you. Your odds will definitely be better than inflation dropping below 3% in 2022.

It turns out that planting a rabbit on your flight won’t cause it to be cancelled; he’ll just get an upgrade while you’re #1 on the list sitting in economy muttering to yourself and watching him from afar.