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I am planning a vacation in a few months to meet my husband at a conference in San Diego. Unfortunately, there is a chance that I will have a work trip the preceding week, meaning my travel plans are up in the air. If I do have a work trip, what would likely happen is I will go on my trip, and then work will pay to "return" me to San Diego rather than home, since it's closer. If I go this route, that would mean I would need to cancel the DCA->SAN leg of my personal trip but keep the SAN->DCA leg, and I would have a couple weeks notice to do so.

I would like to book my personal travel soon, while the prices are still reasonable, and since my work plans are not solidified, I would prefer to purchase both legs. The prices for booking two one-way trips on the same airline (AA) and a single round trip are essentially the same. Since there is the potential I will have to cancel the outbound leg, does it make more sense to purchase the round trip or the two one-ways?

I've already seen this question about round trip vs. two one-ways in the general case, but it doesn't address the issue of potentially having to cancel one leg in advance.

  • I think it makes sense to buy one way tickets, especially as you think it is likely that you need to cancel. And there is no reason not to make it two singles as your return is well away from your arrival. But as this is an opinion and not an answer, I post it as a comment. – Willeke Dec 19 '19 at 19:50
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The situation you've described is one of the few cases where two one-way tickets will almost certainly be the best options.

With two one-way tickets, if you decide to cancel the outbound flight then you will lose the value of the outbound ticket (you might be able to keep a net small amount as a future credit if the ticket price is higher than the change fee, but that's probably unlikely), but that's all.

With a return ticket, because you're changing the outbound flight, you will need to pay the change fee, PLUS the ticket will be re-priced to the fares on the date you make the change, which will most likely mean that the price of the return leg will be higher than when you originally bought the ticket.

The only real disadvantage of booking two separate tickets in a case like this is if you need to cancel the entire trip. If that happens you'll need to pay the change/cancel fee twice (once per ticket), which will likely mean you get nothing back. If you had booked a single return ticket, and if the ticket price was higher than the change fee, then you would at least get something back as a credit - even if it wasn't much!

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