My Window Seat to The Southwest Airlines Debacle


It was 1:30 a.m. on Christmas when Southwest Airlines canceled my family’s flight from Long Island MacArthur Airport to Florida hours before takeoff, catapulting our vacation into the company’s turbulent nationwide meltdown.

Thinking at the time that a recent winter storm simply caused the cancellation — as that was the rationale for us being bumped from our original flight out of LaGuardia International Airport  — my wife and I decided to load the kids in the car after opening gifts and drive four hours to Baltimore, where we’d catch our connecting flight. Getting out of the house was like a scene out of Home Alone, although we managed not to leave any of our children behind.

“It is what it is,” was an oft-repeated refrain as we tried to roll with the punches, thinking that staying positive would prevent any more obstacles from getting in the way of us visiting grandma and Disney World.

What ensued was the most insane trip of our lives — and I’m no stranger to air travel or vacation detours — on what was expected to be the quietest and cheapest travel day of the year. And while challenging, we remain thankful we at least somehow managed to arrive in the Sunshine State and avoid joining the ranks of those poor countless souls we witnessed sleeping in airports on Christmas.

Not long after our arrival by car at Baltimore-Washington International Airport, we learned our flight to Sarasota, Fla. was delayed a few hours as we were told we were waiting for our pilot to arrive from Chicago. But then shortly before boarding time, the news went from bad to worse: Our flight joined the growing list of cancellations. 

About an hour later, my wife scored tickets on a flight from BWI to Fort Lauderdale International Airport, but no sooner than we walked from one gate to the other, that was canceled too, just minutes later. Back to the ticketing line we went, where an agent said there were no available flights to Florida from BWI for days. Turns out BWI ranked fifth for Southwest cancellations nationwide.

“What about a nearby airport?” my wife asked.

“You’ll do that?” the agent asked.

We’d already driven from New York to Maryland. What’s another jaunt across town? As it turned out, there was a flight to Tampa out of Ronald Reagan Airport with five open seats — a half hour drive to catch a plane scheduled to leave in an hour but was already delayed.

My wife looked at the time.

“There’s no time to look at your watch,” the ticket agent said. “These seats are gonna go. Do you want them or not?”

We booked them, hustled back to our car and made our way to Washington, D.C. The scene upon our arrival was, unsurprisingly in hindsight, more chaos. At Reagan, an airport that looks like it hadn’t been updated since its namesake’s administration and makes LaGuardia look like a spaceport, we hurried to wait some more as our new flight was delayed again.

By this time, it was more than 12 hours after we had left home. Mentally preparing myself to suck it up and drive to Florida, we were thrown an unexpected curveball: Our flight wasn’t canceled, and we were finally boarding, albeit to an airport hours from our original destination.

Thankfully our 18-month-old daughter’s first flight itself was uneventful. But we weren’t out of the woods yet once we landed in Tampa. Since our baggage was already checked on the earlier flight to Sarasota, there was no rerouting it, we were told. 

I waded into the baggage claim that was converted into a makeshift staging area packed with a sea of lost luggage as far as the eye could see — a scene that played out at Southwest terminals nationwide. The merry lollipop, reindeer and fireplace decorations outside the baggage claim office belied the defeated mood among passengers waiting hours to learn the fate of their belongings — but at least it was shorter than the absurdly long lines at the ticketing desk where hundreds more passengers were arriving to learn their flights out of Tampa were also canceled.

As it turned out, the luggage we packed with clothes, gifts and essentials was still in Baltimore. The agent gave me a number to call if the airline didn’t contact me the next day. We reached grandma’s 24 hours after we left home — turns out we could’ve driven from New York to Florida in less time than our Southwest misadventure took — but the airline didn’t follow up, so we gave Southwest a ring. The number we were provided was out of order.

At this point, the gravity of our ordeal had fully sunk in. Constant news alerts about Southwest’s epic failure, with an aging computer system reportedly to blame, was blowing up our phones while we were trying to untangle ourselves from the mess. Our calls to the airline for information were repeatedly disconnected without explanation. 

The holiday spirit that at first allowed us to laugh at the ridiculousness had faded. Frustration grew. But we weren’t done yet.

With help from Southwest lacking, my wife searched images posted online of the luggage at Southwest terminals and found a picture of our daughter’s distinct pink-and-purple suitcase at Sarasota International Airport. She nearly cried when the baggage office there confirmed the luggage in the picture was in fact ours — and they also had the baby’s bag. But my wife and my luggage was still in Baltimore and remained so nearly a week later. At least the airline reimbursed us for replacement clothing that we had to buy since we only had the clothes on our back.

While we avoided traveling on the ensuing two days in which Southwest canceled an estimated two-thirds of all its flights to catch up on the backlog, I write this from Orlando, where we’re cautiously optimistic that our plane home from Tampa will depart on time without any issues later this week.

Will our three-hour return flight turn into another day-long disaster? Before we leave the Magic Kingdom, we’ll have to ask Cinderella’s fairy godmother to make sure we get our luggage back and our plane doesn’t turn into a pumpkin. Again.