Southwest offering reimbursement for “reasonable” expenses

Southwest Airlines has been absolutely melting down over the past week. While a winter storm began the downward spiral, but the implosion that ensued seems to have come from within (I’m not sure that we have the full picture yet as to what happened, but it seems that the collapse came on the operations side, whether staffing issues or scheduling issues due to a software collapse), leading to nearly all Southwest flights being cancelled or delayed (with as many as 70% of flights cancelled one day and around 90% of flights cancelled or delayed for days). This has obviously disrupted travel plans significantly (including my own). Southwest is now proactively offering reimbursement for “reasonable” expenses incurred due to the disruption. Your guess is as good as mine as to what will be considered reasonable, but it’s worth keeping receipts.

Customers that have been impacted by Southwest cancellations can go to https://www.southwest.com/traveldisruption/ to look at options for rebooking or requesting a refund. Anyone who has been in the thick of it this week knows that rebooking hasn’t been a realistic option unless you’re willing to travel in January (and while Southwest is allowing a free change within 30 days to those affected, that is valid only between the original city pairs). If you made alternate holiday plans already, you’ll probably prefer a refund over rescheduling your trip for sometime in January.

Be warned that the rebooking process appears to be somewhat of a mess, with Southwest noting in its Frequently Asked Questions that website functionality may be affected. In my case, I don’t think I could rebook online if I wanted to. My family was scheduled to fly on Christmas Eve. After I loaded up our van (in -24 degree wind chill – fun times!) and we started up the road for the 1hr+ drive to the airport, I just happened to pull up the Southwest app to check something unrelated and I saw that our flight was cancelled. We did not receive a text or email about the cancellation from Southwest until after the fact. It was lucky that I pulled up the app as we pulled out of town.

The website was confusing, making it sound like our flight was already rebooked and we should review it and change if need be, but the itinerary itself hadn’t changed. However, we couldn’t change it online. My wife has a Companion Pass and I was flying as her companion, so I couldn’t change my flight without her and she couldn’t change her flight without cancelling mine. I didn’t want to proactively cancel my reservation (in the moment, I didn’t know what we were going to do in terms of rebooking and I didn’t want to take myself off the list of passengers that needed to be reaccommodated if we were going to fly on a different Southwest flight). I tried calling Southwest and waited on hold for more than 2 hours before the system disconnected my call.

In my case, the situation wasn’t that big of a deal. We had to scramble to get ready to celebrate Christmas at home, but we did that and then decided to drive the ~14hrs to visit family, leaving home on the afternoon of Christmas Day. Our situation was far less inconvenient than what others have faced.

I had booked our flights using Southwest points and the Chase Sapphire Reserve, so we would ordinarily qualify for trip delay / cancellation coverage, but since we were at our home airport and we didn’t have any nonrefundable bookings associated with the trip, we didn’t face any costs that would qualify for reimbursement from Chase.

However, it seems that Southwest is offering reimbursement for expenses related to the meltdown. From their FAQs:

I’ve incurred additional expenses (e.g., hotel, other airline tickets, rental car, food, etc.). Can I receive a reimbursement?

If you have been impacted by a flight cancellation or significant flight delay between December 24, 2022, and January 2, 2023, you may submit receipts for consideration via Email Us on Southwest.com. We will honor reasonable requests for reimbursement for meals, hotel, and alternate transportation.

It is very unclear as to what expenses they will reimburse and what they consider “reasonable”. While the wording suggests a cash reimbursement, I wouldn’t be surprised if they offer Southwest vouchers.

Let’s be clear: this meltdown sounds like it was largely Southwest’s fault (the storm obviously wasn’t, but everyone else was back to business as usual within a day or two and Southwest continued to cancel or delay around 90% of its flights for days afterward). I think that reimbursements here is the “right thing to do” and Southwest may well face government-mandated accountability eventually. But the fact is that based on current rules, they aren’t yet mandated to do much.  The fact that they are creating a mechanism to try to do right by customers is a step in the right direction.

Unfortunately, we don’t yet know how big that step will be. My flight to visit family was cancelled, so we drove ~14 hours. Based on the FAQs, I would expect that we should qualify for reimbursement of gas and food for the road trip (lucky for Southwest, nothing along the highway was open for dinner on Christmas night, so they’re only on the hook for some instant mac and cheese at the Pilot travel center that night lol).

If we had rented a car, I suppose we could have asked for reimbursement of that cost (we drove our own car). Will they cover the cost of the hotel we booked on the way down since we couldn’t make the entire drive in a day? I will certainly submit the receipt and request it, but I don’t know. What about the return journey? Our return flight isn’t yet cancelled, but we obviously won’t take it since we need to drive our car home.

What about someone who booked an alternative flight on another carrier? Based on the FAQs, I would think that they could be reimbursed, but is there a limit? I saw someone post a screen shot on Twitter of a Southwest flight to Denver that was available for sale for $1800 asking whether that would be considered “reasonable”. We don’t have any idea what will be deemed reasonable here — at this point, Southwest is just saying that you can submit your requests for “consideration” — it doesn’t commit to reimbursement but rather commits to consider it and grant reimbursement if they deem it reasonable. The moral of the story there is don’t book something super-expensive if you can’t live with not being reimbursed. We just don’t know what Southwest will reimburse and I can’t imagine how long it is going to take for them to weed through the backlog of reimbursement requests.

In my case, if they cancel my flight home, perhaps I can get some cancellation coverage from Chase (since we paid the taxes for the award flights home using a Chase card). However, Chase won’t cover alternate transportation, so I don’t expect they will be willing to cover gas and hotel for the ride home since Southwest is offering to rebook for free. At the end of the day, we’ll just spend what we ordinarily would and see what coverage / reimbursements come through. That said, based on the phone notification I got a few minutes ago, it looks like there may be a light at the end of the tunnel in terms of flights getting back on track.

Bottom line

If you have been affected by the meltdown, I think it’s absolutely worth submitting receipts for any unexpected expenses you’ve incurred due to Southwest cancellations. I imagine some readers may have been on the hook for significant nonrefundable hotel costs and/or you may have needed to book last-minute fares on other airlines whether to get to family domestically or to position for an award flight somewhere else. It sounds like Southwest may reimburse people to some extent, but the squeaky wheel gets the grease, so you’ll need to squeak. Just expect to be in a holding patter for what will likely be weeks if not months before reimbursements (if any) start rolling in.

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