Luv is Blind - How Southwest Mishandled the Holiday Travel Meltdown

Saturday, Christmas Eve

We're at home with my family in OKC opening presents at 10 pm before we fly out Christmas morning to spend time with Kelly's family.

We're supposed to fly out the next morning at 7 am to see Kelly's mom, sister, and brother who have come to Boston from Vietnam for the holidays.

At 10:33 pm, we get a text:

We scramble to call to rebook, it takes over an hour for someone from Southwest to pick up. We find out that there's one seat left on a flight on Christmas Day at 4 pm, and the next available flight to Boston isn't until Thursday, December 29.

Stuck in this scenario, we rebook me for the Southwest flight on Christmas Day and look for other options for Kelly to get in earlier so that she can enjoy Christmas Day with her family.

We book Kelly on a $500 one-way flight from OKC to BOS on American Airlines at 8 am.

Sunday, Christmas Day

Kelly arrives on time at Boston Logan at 3 PM ET. Unscathed.

My Southwest flight starts to get delayed. I had a bad feeling about how the evening was going to unfold.

I get to the airport, and Southwest baggage check has 3 employees working it and is completely overwhelmed.

After seeing lines at a standstill, I end up showing people how to use the kiosks to tag their bags so that the lines can move more quickly. Still, it takes 1.5-2 hour wait to check bags.

After a 1.5 hr delay, we depart OKC at 6 pm.

I land in Chicago around 8 pm, this plane is supposed to go directly to Boston after Chicago so I'm instructed to stay on the flight.

A few minutes later, the flight crew tell us that we need to deboard. Confused, I ask what's going on and a flight attendant tells me, "Not enough crew to fly."

I wait an hour, and unsure if we're going to fly out Christmas evening, then I call to see if there are other options.

While I'm on the call, my boarding pass from Chicago to Boston disappears.

The only thing left is my return flight back to Austin.

It's almost 11 pm now, and after two hours a staff member looks into rebooking me for the following day. She says, "I can't rebook you because the flight hasn't technically been canceled yet, I've escalated and am on hold to get help."

I stay on hold, hopeful they can rebook me.

Then I hear a beep, beep, beep, the sound when an iPhone call ends.

Now I'm really stranded.

I just spent 2 hours on a call, and the lines to talk to staff at Midway Airport wrap all the way down the terminal. There's no way I'm getting any help any time soon.

This tweet ends up in an Apple News Article about the Southwest "Disaster at Midway".  

I fold, book a Marriott hotel, hit up an old friend and coworker from GE, and grab an Uber to meet him for a midnight snack.

Monday, December 26th

My guy shows up at midnight to share a meal with me. Thank you for being there, Eric!

I check into a Marriott hotel near Chinatown that cost around $360 since all hotels near Midway are fully booked.

In the morning, I'm still stuck without a Southwest Boarding pass out of  Chicago.

So, I rebook a JetBlue flight from Chicago O'hare to Boston Logan for $320.

With a detour in Chicago, I try to make the most of it. Thanks to Eric, Chris, Jenny, Trent, and Sophie, it turns out to be a really cold, yet fun day in Chicago.

Tuesday, December 27

The JetBlue flight I take gets delayed by 4 hours, but ultimately flies out.

After a few cancellations, multiple delays, two airlines, and 36 hours after leaving OKC, I land at Boston Logan at 3:40 am.

Which is longer than a typical trip to Vietnam from door to door.

The next day, unprompted and unrequested, JetBlue sends me a travel credit for $100 for the 4-hour delay. Wow.

The proactive customer service is a stark contrast to what I've been experiencing with Southwest.

Wednesday, December 28

On the same day, Southwest drops their obligatory apology video because at this point the travel disruptions obviously weren't solely weather-related, since every other airline operated with minimal disruptions.

I submit my story and receipts as requested and wait.

Monday, January 3

Kelly and I received 25K points each for future travel as a "gesture of goodwill" which is worth around $600 of flight credits. This is a really great start in helping to reimburse the $1,500 of expenses we had to incur for 2 new flights, a hotel stay, Uber, etc.

Though, I was still expecting to be reimbursed for the canceled flight and expenses that we incurred, at least partially.

Thursday, January 5

My case gets escalated.

Friday, January 6

Still waiting...

Tuesday, January 10th

Southwest contacts me back with "Reasonable requests for reimbursement for meals, hotel accommodations, and alternative transportations (e.g. rental cars and tickets on other airlines) were honored" and then proceeds NOT to honor the $1,500 of receipts.

Oh and the "At this time, we consider your reimbursement request complete."

After posting on Instagram about this, a friend suggested that I submit a complaint to the DOT. So, I figured why not.

The Department of Transportation (DOT) has said it will take action if Southwest fails to honor its commitments to passengers traveling between December 24 and January 2 whose flights were delayed or canceled under “controllable circumstances.”

Reasonable reimbursement should include, according to the DOT:

• Meals for passengers who waited three or more hours for a new flight
• Hotel accommodations for passengers with overnight delays or cancellations
• Ground transportation to and from hotels for passengers with overnight delays or cancellations

Seems like the DOT is getting a lot of similar complaints and passing those on to Southwest. To which Southwest said, "Southwest intends to, and is making every effort, to initiate refunds and reimbursements as we've stated in our Customer Service Plan -- which is in alignment with the corresponding regulations."

However, "to initiate refunds and reimbursements" is really different than actually honoring refunds and reimbursements.

Wednesday, January 11

Southwest sends a follow-up email to claim the payment.

I am hesitant to accept the $75 offer as it feels like an incomplete and unfair resolution.

It seems as though Southwest is attempting to pay out a minimal amount while also effectively dodging customers seeking further compensation by presenting this as a "full and final settlement."

Thursday, January 12

That brings us to today.

During the holiday meltdown, Southwest canceled over 16,700 flights in a 10-day period, which is more than the previous 10 months combined. It's estimated that it'll cost Southwest up to $825 million.

I can see why Southwest is shelling out 25K points per impacted customer. This approach allows them to offset costs without utilizing any cash in the short run.

It seems that any cash compensation offered to customers to fulfill DOT requirements is minimal in comparison to their actual costs, and may be done in hopes that customers will accept it as a final resolution.

Although I haven't received a refund for my flight cancellation, refunds for flight cancellations are often given as "flight credit" to customers' Southwest accounts, which allows the company to retain the cash while still providing a form of compensation.

At this point, Southwest is in a really tough position of trying to manage cash burn, stakeholder expectations, and customer recovery which are all opposing factors.

• Do you do customer right and burn through even more cash? Will these customers even fly with you anymore even if you do?
• Or do you turn a blind eye, pay out as little as you can, and pass the cost of your blunder onto your customers instead?

I think we know the route that Southwest is incentivized to go.

Takeaways

At this point, I'm considering the costs that we took on during that fiasco as a sunk cost. I'll submit yet another reimbursement request and hope that my case was just an oversight.

I have heard from one friend that Southwest has reimbursed them an acceptable amount, but I've heard from many, many others who are in my shoes with little to no reimbursements.

Here are a few takeaways that I've learned from the entire experience.

• Try not to fly on holidays, particularly Thanksgiving, Christmas, and New Year's. These tend to be some of the most heavily traveled days where airlines are operating at max capacity, not leaving a lot of room for error. This is something that I've typically tried to avoid and was previously easier to do since Kelly's parents were usually in Vietnam. Now that they received their green card, we may end up needing to split holidays between families to avoid this kind of travel disruption.
• Be Proactive Rather Than Reactive. Props to JetBlue for proactively reaching out after the 4-hour travel delay and automatically crediting me $100. I've never seen that before. You usually have to call and ask for reimbursement or submit something online. The feeling of not having to do anything and for a corporation to take the initiative is so incredibly refreshing.
• Turn Delays into Detours - Inevitably you'll run into obstacles when traveling or when trying to navigate life in general. Delays and mishaps are bound to be a part of the journey. But they don't have to be all bad. With a little bit of creativity and some good friends, you can turn it into a memorable detour.

As a Companion Passholder and A-List member, I've been a big advocate for Southwest over the years. Whether it was showing people how to earn a Companion Pass or referencing Southwest as a beacon for company culture and investing in employees who then take care of their customers.

I'd like to believe that Southwest is simply still overwhelmed with meeting customer demands while also trying to operate and improve its operations. Thus, they're bound to miss reimbursing a minority of people for whatever reason.

But there's a skeptical part of me that's starting to wonder if Southwest is still the same company with the same culture and values as when Herb Kelleher started it.

I'll probably keep flying Southwest since we have the Companion Pass through the end of 2023, which begs the question maybe I'm the one who's blindly in love?