My Terrible, Horrible, No Good, Very Bad Travel Day (With A Happy Ending)

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Typically, our travels are pretty straightforward. We fly from home to where we want to go, and back home again. For one particular trip that happened a couple of years ago, as it turned out, I needed to be in Washington D.C. for the weekend to attend Frequent Traveler University. From there I would fly to Austin and meet up with Sharon, who would be flying there direct from Orlando. From there we were due to visit Schlitterbahn, our favorite Candlewood Suites and some of our favorite restaurants in the area.

Our travels looked like this:

Despite my initial mistake of booking my flights to the wrong airport in Washington, everything about the trip was going fine; I got to spend some time walking around Washington (one of my favorite places) with friends for the weekend while Sharon stayed home with the dog.

That is, everything was going fine until Sunday, which was the day Sharon was due to fly to Austin and I was due to fly from Washington D.C. and meet her several hours later. Sharon’s flight went off without a hitch. Around noon she was well on her way to Texas, somewhere over the Gulf of Mexico, when I opened the Southwest app to check on my flight.

Not just delayed, but canceled. I had no idea when this happened because I never received any notification from Southwest. No phone call, text message or push notification to my phone. Nothing. I don’t understand how can they not tell you when your flight is canceled, but here’s Southwest and Citi’s response to why that happened. Anyway, I clicked on the “Select new Flight” button and received a popup box telling me I couldn’t rebook on the app and that I needed to call Southwest customer service. When I called, I was told that due to high call volume my wait time would be 135 minutes. That’s 2 1/4 hours!!!! At a time like this, ain’t no one got time for that. 

I decided to look for flights on Southwest out of Reagan National and discovered the flight I was on is the only non-stop Southwest flight between there and Austin. There were also no other connecting flights available for Sunday night. OK, let’s see if anything’s available on Monday morning to either Austin or San Antonio.

What about from Baltimore? That’s a big airport for Southwest. Maybe they’ll have something available?

I began to sense a trend and realized there was no way I was getting out of Washington D.C. on Southwest, so I needed to think of other options. It was already 12:30 pm, the clock was ticking and there aren’t a whole bunch of options out of Reagan National. I checked Skyscanner and found that the only other airline that flew from any airport in Washington to Austin was United. I begrudgingly pulled up the United app and looked for flights, as in a pinch I’d be willing to go against my boycott of the airline if it meant I’d get to see my wife that evening. Fortunately, or unfortunately, they didn’t have any available flights.

The only other possibility was on Delta. I pulled up the Delta app and found that they had a flight that would get me to Texas. Problem was that the flight was to San Antonio, not Austin, and there was a connection in Atlanta. The flight also wouldn’t be landing until around midnight. Not exactly the type of first night we were planning in Texas. To make matters worse, the ticket was really expensive. Like $750 expensive. As in “I’m not paying that much for a one-way ticket” expensive. I checked to see how many SkyMiles Delta wanted for the ticket. 56,000! For a one-way ticket from Washington to San Antonio. If circumstances were different, I might have balked but I wanted to get to Texas and be with Sharon so I booked it.

Here’s the text I sent to Sharon once her plane landed in Austin:

And that’s why I love my wife.

Given the circumstances, I decided to head to the airport ultra-early, “just in case.” Just in case of what, I don’t know. But, you know, just in case. I headed right to the SkyClub where I found out the hard way that I always need to bring my American Express Platinum card when I travel. Since I was lacking my “Get Into The SkyClub For Free Card,” I either had to pay the $59 fee or sit at the gate for hours. I paid the money, made myself comfortable and waited for my flight (I’d no longer be able to pay for access to a Sky Club if I forgot my Platinum AMEX nowadays).

Then a notification popped up on my phone. Due to weather, my flight to Atlanta was delayed by 25 minutes. I only had an hour connection in Atlanta and I didn’t want to repeat the sprint I had to make the last time we connected there.

While I sat there in Washington and watched the weather map, it wasn’t pretty.

It turned out the weather was clearing and we left Washington right around the delayed time of 7:30. We had to get to Atlanta in time to make my connecting flight. I spent much of the flight looking up hotels near Atlanta airport in case I missed the connection. I paid the taxes on the Delta award flight with my Sapphire Reserve so if I got stranded, they’d reimburse me for the hotel and transportation.

While in flight I also tried, in vain, to reach Delta via Twitter and have them save me a spot on the plane the next morning. They never replied, but that’s another blog post altogether. We landed in Atlanta and here I was again, standing on a plane and looking at my watch and hoping I could make my connection. We ended up landing at the end of one terminal and my flight to San Antonio was leaving from the other side of the airport, one stop away on the subway. Here we go. Off the plane, through the terminal, down the escalator, run on the train, one-stop, off the train, walk up the escalator, through to the end of the terminal to my gate. Huffing and puffing my way there, I arrived and saw the line of people waiting to board. I made it! It was only 18 minutes before the scheduled departure but the flight was running late and we didn’t leave the gate until 10:14 PM.

I was on the plane. I was going to get to Texas that night, which was something that was really in doubt just 10 hours before. Delta was nice enough to give me a Comfort Plus seat. This was the first time I’ve ever gotten an upgrade so I didn’t even know what Comfort Plus included, except for more legroom which was greatly appreciated. I asked my seat buddy what we get and he said “Not much, but you do get free booze.” I do know enough to understand what that means when you’re flying Delta. Nothing like a Woodford Reserve or two to take the edge off a stressful day.

There you go. Twelve of the most stressful travel hours I’ve experienced. It was made even worse because Sharon wasn’t with me. She wasn’t even home but she was already in Texas, waiting for me to arrive. If we were home and this happened, we might have called off the trip. We also could have just come home and left the next morning. This was the worst-case setup for a flight cancellation. Weather, multiple flights and multiple cities. I’m actually quite proud I found a way to get to Texas. Granted, it was expensive but this is a good example of how valuable points and miles can be. I was able to redeem 56,000 SkyMiles for my ticket which would have otherwise cost $750. I earned those miles by signing up for the Delta Gold AMEX card and I can replace them by signing up for a different Delta AMEX or an American Express card that earns Membership Rewards points (which you can transfer to Delta). It was a lot easier to let go of the miles instead of needing to pay $750.

In the end, we had a great two days in Texas Hill country and I don’t regret a thing.

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