How Trip Insurance Actually Paid Off For Me

Posted in American Airlines, business, Domestic US, In the Air

On Friday, I received a check for $534 in the mail. It was the final step in a journey that I never believed would have a happy ending. Through kidney stones, credit cards, and PDF uploads, I was able to cash in on my credit card’s travel insurance feature and I’ve lived to tell the tale.

How it all started.

I’m not someone who buys trip insurance. When it’s offered to me while purchasing a flight, I scoff and buy the tickets without it. This isn’t because I have something against trip insurance or anything, I’ve just been told time and time again not to buy optional insurance when it comes to traveling, be it with rental cars or airline tickets or anything else. So when a kidney stone struck hard in the middle of the night before a flight, I thought I was out of luck.

My flight was scheduled to leave at 6am for Miami, but this kidney stone was vicious. If you’ve never had one, it feels like an alien is giving birth in your lower back. I tried to make the pain go away with the pills my urologist had prescribed, but to no avail. My only choice was to head to the hospital. Fun fact: Uber makes a great ambulance. I got from my house to Cedars-Sinai in under ten minutes at 3am. I believe that to be a world record.

In any case, I was seen very quickly and had hopes of getting released with enough time to still make my flight. Unfortunately, the doctors decided that wretched stone needed to come out immediately. I was scheduled for emergency surgery later in the day and that meant that my trip to Miami was going to disappear along with my stone.

My big plan.

After I returned home from the surgery, I lamented the fact that over $500 in non-refundable airfare was gone. I knew I’d still have the value of the ticket (minus change fees) available to me, but it seemed like such a shame to let the kidney stone defeat me financially as well as morally. In the back of my head, I vaguely remembered something about trip insurance as a benefit of my Chase Ink Plus card. I did some digging and found this:

Trip Cancellation/Interruption Insurance^

If your trip is canceled or cut short by sickness,
severe weather and other covered situations,
you can be reimbursed up to $5,000 per trip for
your pre-paid, non-refundable travel expenses,
including passenger fares, tours, and hotels.

I was nearly certain that emergency surgery qualified as sickness, so I called Chase and sure enough, I was good to go. I was referred to their insurance carrier, Crawford & Company, and all I had to do was convince them to give me money. Easier said than done, right? As an insurance company, I figured they’d do everything they could to get out of it. I was wrong.

The agent I was dealing with outlined the documentation she needed to process the claim. I had to come up with:

  • A copy of my ticket receipt
  • The credit card statement listing the charge
  • American Airlines’ cancellation policy
  • A letter from my doctor’s office detailing the malady

Gathering all of the files together was a little inconvenient, but nothing out of the ordinary. Of course they needed me to prove that (a) I was indeed sick, (b) had purchased the ticket with my Chase Ink Plus, and (c) didn’t use the ticket. I turned everything into PDFs and emailed all of the documents over. Once the claims agent received all of that, I had two options. I could either use the ticket value for another ticket and Crawford would reimburse my change fee or I could wait a year and get the full value back. I decided to wait.

In my iCal, I put a little reminder of when a year would be up and then I promptly forgot all about it.

The road to fame and fortune a satisfying check.

The year mark came up a few weeks ago. Sure enough, I checked my calendar and saw that it was time to check back in with Crawford. The same agent was there to assist me and she informed me there was one more hoop to jump through. I had to get American to confirm that I didn’t use the ticket over the past year. I called in and, while it was somewhat difficult to explain what I needed, the AAdvantage agent finally came through and provided me a very simple email:

“This copy indicates the ticket was unused and is currently expired.”

That’s all I needed to get. Sure enough, the refund was processed and a $534 check arrived in my mailbox last week. I truly never thought the system would work. I figured they’d find some technicality to get out of paying, but lo and behold, they came through.


This is all to say that trip insurance can actually be valuable. While I still don’t think I’d purchase it directly from an airline while I’m buying tickets, knowing that my credit card benefit actually works makes me feel a lot safer in the face of trip interruptions. After all, you never know when a kidney stone will strike again.


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  1. Congratulations! I too would have expected a different outcome, but YOU WON!
    The only item that confuses me is why they made you wait ONE YEAR for the refund. Any ideas?

    • @Cook, the year-long wait is totally understandable in my book. Basically, I had to wait until the ticket was expired and no longer usable. American keeps the value of cancelled tickets in your account for a year and after that, you lose the value. Had I used the ticket within the year, the trip insurance would have paid me the $200 change fee instead of the full $534 amount. I decided to wait so I could get the full amount of the refund.

  2. I think the real moral isn’t about insurance as much as knowing your card benefits! We often confine ourselves to signup bonuses and earning rates, but don’t always consider the other benefits like trip insurance, rental car protection, extended warranties, or return periods.
    It would be awesome to have a post on some of the more “interesting” card benefits and what their terms are.

    Congrats on an easy claim!

  3. Great post! Thank you for sharing.
    What if it is an award ticket and I use the card just to pay for the taxes & fees, would I have the same coverage?

  4. Awesome Chubb/Crawford insurance worked for you as well as it did me. I have used the trip cancellation/delay insurance as well as the baggage delay insurance and been paid out within 2 weeks each time. As long as you have the proof of everything its super easy.

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