Travel Insurance Didn’t Cover Everything. Now What?
- Christine Hardenberger

- 46 minutes ago
- 3 min read

I've been out exploring the world (and working a LOT), but I am back and have I got a story for you.
This one is about what happens when travel insurance does not neatly save the day.
Because sometimes it does not.
A few weeks ago as my family waited in the airport to head to Ireland, our outbound flight was canceled. Not delayed. Canceled. Worse, United could not get us to Dublin in time to meet our tour.
Yes, we should have flown in a day early. No, we could not make that work with everyone’s schedules. Choices were made.
So there we were, five adults, no flight, and a tour in Ireland that was about to leave without us.
I jumped into travel agent mode and rebooked our flights on the spot. $4,200. Just like that.
Then came the hotel situation. It was now 3am and United offered one room for five exhausted adults, which was not happening unless we were filming some kind of reality show. I booked two rooms. Oh, and I booked them for two nights so we wouldn't be kicked out at 11am when our new flight didn't leave until 5pm. Another $700.
All in, I was out about $5,000 in a matter of hours.
We all had travel insurance, so I wasn't worried about any of this. I filed the claim. Easy, right?
Not exactly.
The flight cancellation was due to a maintenance issue. That is not a covered reason unless you miss more than 50% of your trip. We had not. We only missed the first day.
This is where most people hit a wall. Claim denied. End of story.
Nope. I still wasn't worried.
I recommend Chubb for most of my clients and I use them for myself. One of the reasons is that they actively try to find coverage when they can. They are not looking for reasons to say no.
They covered the hotel. They paid a portion under trip delay. They reimbursed the missed day of the tour.
Total reimbursement was about $3,600.
That is not the full $5,000 I spent, but it's a heck of a lot better than getting nothing back. However, there was still about $1,400 sitting out there.
Was I out of luck?
Nope. Travel insurance is not always the only path to getting your money back.
I filed directly with United for a refund on the canceled flight leg. That amount, alone, was more than enough to cover the remaining $1,400.
Done. I was made whole.
Here is the takeaway.
First, insurance is worth it even if everything isn't covered. Getting $3,600 back is a lot better than eating $5,000.
Second, the company behind the policy matters. A lot. Some companies look for technicalities to deny claims. Others look for ways to pay them. That difference matters, as you can see from my story.
Third, this is not a one-lane road. Insurance is one piece. Airline refunds, supplier policies, and knowing how to navigate all of it is the rest of the picture.This is why you have me on your side. I can help you navigate all of this to ensure you recoup as much as possible.
This is why I do not recommend grabbing the cheapest policy you can find or assuming your credit card has you covered. Those options often look fine until something actually goes wrong.
If you want to make sure you actually have the right coverage and know what to do if something goes wrong, that is where I help.
If you have a trip on the horizon and want to make sure you are properly covered, let’s take a look at it before you need it.
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