Multiple flight changes - any risk?

Question

My wife is helping out with a family member who has some medical issues in another city in the United States (halfway across the country). Initially she planned to go for only two days, as it wasn't clear what the situation was, but when it became clear it was more serious we rebooked her flight (on Southwest) for a few days later.

Now, it's become clear she needs to stay yet another few days, and I'm rebooking her again. So far this hasn't caused any problems - there are a few flights a day between our airports and one always seems to be the same price as the initial one - but I'm wondering if there are eventual consequences for rebooking flights quite a few times, especially with only a day or two's notice each time.

I don't see anything regarding limiting rebookings in the contract of carriage, but I'm really asking from a more general sense: is this likely to cause issues in the future, either with security, with the airline, or anything else I'm missing? Should I do anything to let Southwest know why we're making these changes (as they're related to a medical situation)?

If it's relevant, they're nonrefundable tickets (that I'm not asking for a refund for, of course, just rebooking).

Answer 1

I've never heard of any limits or problems with this. Given that Southwest allows changes without fee, they should certainly not be surprised when people with rapidly changing plans make frequent changes.

They do have a rule that you can't make a reservation that you are "obviously" not planning to fly; e.g. two flights at overlapping times on the same day, or two flights departing from two distant cities on the same day. See 2 (a) (iii) (f) in the Contract of Carriage. So don't try to make "backup" reservations. But otherwise I can't think of any problems.

It's possible this will increase her chances of getting additional security screening. There isn't anything she could do about that, and explaining your plans to the airline wouldn't help. So it would be wise to allow extra time in case security takes longer than expected - but one should always do that anyway, because one can always be randomly selected for extra screening even if everything is normal.

Answer 2

No, there is no issues with a 'reasonable' number of changes so long as fare you are immediately changing from has no specific restrictions.

Southwest generally has few restrictions on changes, you just have to pay any fare difference.

What is reasonable? 1, 3, 5? Still not entirely unusual.

Where it becomes a problem is if you demonstrate a history of chronic changes where they think you're trying to game the rules.