I've reserved a flight for my family of five in October, with four paid reservations (with points) and one Companion fare (for my wife). I've flown Southwest for years and never bothered with EarlyBird check-in (EBCI), but I'm most often alone, so picking a nice seat is easy. This time, I'm considering adding the EBCI to help ensure we can all sit together. I also understand that your time of EBCI purchase is used to place you in the line for boarding positions.
So, I'm left with a bit of a dilema, if I understand correctly that EBCI is not refunded on "cancelled" reservations (as that's what I'd have to do to my wife's Companion res to make a change to my other paid reservations). Am I right in thinking this odd logic on SW's part means I can either buy EBCI now for all my 5 tickets and just lose the $25 if the price goes down and I have to rebook to get the refund OR I should wait until much closer to the actual flight date before buying EBCI (when the fare's unlikely to drop any further)?
I'm willing to spend the extra for the potential boarding advantage, but don't really want to just throw money away (either by not rebooking all the flights if prices drop or losing what I've spent on the Companion EBCI). Perhaps I can get around the requirement of cancelling and then rebooking the Companion fare for paid fare changes by calling (instead of doing it through the site)?
You can add EBCI now and if the price of the flight changes you can call reservations and they should be able to reprice the flight at the lower cost without you having to cancel your flight and your EB would stay attached (as long as changes are made more than 36 hours before the flight). You might also be able to use the chat function of the SW app for getting the change made and avoid the potential hold times on the phone.
If you bought EBCI for four people and left your wife to the regular check-in process, other than not standing together in line, I think it would be fine to hold a spot for her when you boarded.
So either buying it now for her and then hopefully Southwest can transfer it if you did need to rebook (or maybe they can't and it would be lost), or buying it for her separately later, for a position that won't be as good as yours, but still before the general check-ins, or not buying it for her at all - in any of these scenarios I think she'll end up sitting in the same seat.
Home airport MDW, frequent visitor to MCO to see the mouse.