My flight was canceled but I got most of my costs covered (after 3 months)

As demand for flights jumped over the summer, airlines struggled to keep up, and delays and cancellations became the theme of the season.

I wrote more articles than I cared to count about what was going on in the airline industry and what travelers could do to avoid the worst of the issues.

One piece of advice that kept coming up: Book flights that departed early in the day. Early flights were (and remain) the least likely to get canceled because airlines' operational issues tend to get worse as any given day goes on.

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But, you know how sometimes you hear the same thing over and over and still think, "yeah, but it won't happen to me"?

Well ... it did.

What did I do?

Here was my original plan:

  • Flight date and time: Sunday, Aug. 7, at 6 p.m. EDT.

  • Airline: A Delta Connection flight operated by Endeavor Air booked through Delta Air Lines.

  • Destination: Myrtle Beach, South Carolina, and then I planned to fly home one week later.

I checked in, as usual, the night before my departure, as did a friend who was planning to fly down with me on his own ticket.

The morning of the flight, my friend texted me that he'd gotten a notification that our flight had been canceled.

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So, the scramble was on. We both had to be in the Carolinas ASAP. My friend was traveling to pick up a car, which he needed for a new job. And I had to work on Monday, so the middle-of-the-weekday flight just wasn't feasible for me.

(My editor later told me it would have been fine to take the day off, but I didn't know that in those first panicked hours.)

My editor making fun of me (foreground, with bass clarinet) during my train "smoke break" in Washington.
My editor making fun of me (foreground, with bass clarinet) during my train "smoke break" in Washington.

My friend and I considered renting a car and driving through the night, but car rentals were expensive, and I was too tired from the stress to feel up to a 12-hour road trip.

In the end, my partner – who was booked on Spirit Airlines – left for Myrtle Beach from LaGuardia that Sunday with his cat. Our friend took a flight later in the week and got his car in the end.

I took the train on Monday, so I could work on the way.

But I was still left with questions: Since I didn't show up for the rebooked departing flight, would my return flight also be voided? I decided not to risk it and canceled my entire original itinerary and got a full refund. Then I booked a Spirit Airlines flight back to New York for Aug. 14.

I (and my partner's bass clarinet) did ultimately get where I needed to go.
I (and my partner's bass clarinet) did ultimately get where I needed to go.

I also have travel insurance through my credit card, and I decided to test it out. It took much longer than the company said it would to process my claim – about three months as opposed to five business days – but I did recoup a lot of my costs.

What was I entitled to?

I knew that I was owed a full refund from my original itinerary because the airline canceled my departing flight. Delta Air Lines made it easier to claim an e-credit for future use, but I was so annoyed I decided I wanted the cash (even though I still fly that airline all the time).

Although the airline said I should expect a refund in seven business days, it took almost two months to reflect in my account. However, I did receive the money as a credit on the card I used to pay for the tickets.

A row of Delta Air Lines planes, with a regional jet in the foreground similar to the one I was scheduled to fly on to Myrtle Beach.
A row of Delta Air Lines planes, with a regional jet in the foreground similar to the one I was scheduled to fly on to Myrtle Beach.

More arduous (but equally fruitful) was the insurance claim process. That took the better part of three months and required a LOT of documentation. I ultimately needed to provide:

  • Confirmation and payment receipt of my original itinerary.

  • Copy of the credit card statement from the month I purchased the ticket.

  • Confirmation of the flight cancellation by Delta.

  • Explanation of why the flight was canceled.

  • Confirmation of the flight the airline rebooked me on.

  • Receipt for the train ticket.

  • Receipt for the Uber from my apartment to Penn Station.

  • Receipt for snacks and meals during the trip down.

  • Copy of previous Delta itineraries because I used a credit from a prior flight to cover part of the cost of the ticket associated with the claim.

  • Receipt for the new flight home.

  • Confirmation of my refund request to Delta.

I also spent a considerable amount of time waiting on hold. As the automated message kept telling me, the insurance company was dealing with an unusually high volume of claims and that things were taking a while. My adjuster encouraged me to submit more receipts, including for food on my trip, which I didn't realize could be covered.

The adjuster called me with specific, helpful information a few times during the process, but I never had a way to reach her directly from my end. Calls were routed through a call center and emails through a generic inbox, and although everyone was friendly and understanding, they were rarely able to provide the information I was looking for when I reached out myself.

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In the end, after much back-and-forth and a few requests for additional documents, the insurance company approved most of the expenses I was seeking: the train ticket to Myrtle Beach, the early morning Uber from my apartment to Penn Station and all the snacks and meals I ate along the way. That's in addition to the full refund I received from Delta. The only thing the insurance didn't ultimately cover was the Spirit flight I purchased to get back to New York.

Where did I go wrong?

"I don’t really hear anything you did particularly wrong except the notion that you took that flight late in the day, especially on a small regional carrier," Jf Oyster, owner of Outward Travel in Colorado, told me. "You are dealing with that high degree of risk of a busy small airport on a small carrier late in the day, You’re almost asking for a cancellation in that situation."

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Otherwise, Oyster pointed out, I fared pretty well, especially considering how much my travel insurance ultimately covered.

"I think you kind of lucked out there, but most travel insurance is pretty amenable to the customer," he said.

As we all start to think about winter travel, I wish I could say I won't make the same mistake again, but I definitely just booked myself a 6 p.m. flight to get home to New York from Denver at the end of a snowboarding trip in February.

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Oyster said there are other ways people can set themselves up for a smoother experience this winter.

"Travel as light as possible," he said. "Particularly with the holidays, you may have to check a bag, but if you can avoid checking a bag, it’s going to be worth it."

The plane that ultimately took me home to New York from Myrtle Beach.
The plane that ultimately took me home to New York from Myrtle Beach.

Oyster also recommends getting travel insurance for every trip, and considering working with a travel adviser who can assist when something goes wrong.

Above all, "just be patient. Keep an eye on your flights," Oyster said, and be proactive about getting in touch with customer service if there are any changes to your itinerary. "The sooner you’re in that queue, the sooner you’ll have an advantage over people who are not paying attention or not making that call or hoping for the best."

This article originally appeared on USA TODAY: How our airline reporter handled his own flight cancellation