We’ve been traveling for over 6 years...and have flown over 50 times. With all of this time in the air, it might surprise you that we finally hit the travel milestone of dealing with a cancelled flight.

Maybe call it a “bad part of traveling” bucket list. It wasn’t something we were really wanting to experience but it's almost a numbers game it was bound to happen at some point.

And here we are, the unlucky ones. And this wasn’t a simple cancelled flight. Oh, no...it was more a snowball of misfortunate events making us think we must be cursed.

To watch everything unfold so spectacularly, horribly was anything but fun. But you live and you learn and now we have a fun story to tell at parties...or for the blog.

Getting the Flight Cancelled: Our Story

As with most travel stories, this one begins with us driving to the airport after a fun weekend where we got to celebrate an amazing couple getting married. The flight (which was a direct flight) kept getting delayed all day long but we were innocent hopefuls.

Only a few minutes out from the rental car return we got the dreaded text that our flight had indeed been cancelled. Turns out you can only delay a flight for so long.

We had already delayed the return of the rental car as late as possible without having to pay another $60. This was already an interesting start to our return journey home because that amount of money is pretty steep for just a few more hours but hey, what do we know.

So we returned the car anyway and headed to the airline's check-in desk to see what we could do about our flight that no longer existed. We were flying first class so getting the change was going to be even more confusing.

We were told that they would try finding us a flight with first-class seats but getting us to our final destination would be the top priority. When asked how we would be reimbursed for the seat downgrade, we were told we have to contact refunds once we arrived at our final destination.

After some searching, the front desk placed us on a flight with a layover leaving two days later. So we negotiated to get a hotel voucher for two nights and meal vouchers as well.

Ready to Unwind at the Hotel

Once at the hotel their staff informed us that the meal vouchers aren’t accepted anywhere...not even the airports own restaurants. Luckily the room voucher was a go.

Once in the room, we double-checked our new flight ticket and saw that we were indeed bumped down to economy...with no seat assignment. Now we were already semi-prepared for the seat downgrade but to not even get an assigned seat seemed a little silly.

We called the helpline where they instructed us to go back to the airport and talk to the front desk again as they are the only ones with clearance to even pick a seat. Again, seems a little silly but we didn't know any better.

If we have a new flight, and we’re already downgrading to a lower seat, can’t they just give us an assignment?!

Glimmer of (False) Hope

So we made our way back to the airport (a lot of shuttle and Lyft rides occurred during this adventure) and talked to a new front desk worker who was definitely a step up from the first.

Unfortunately, she started with a lot of bad news. We would have to wait for our seat assignment the day of the flight, nothing they could do about that. Also, they give the meal voucher in hopes it's accepted but there is nothing they can do if no one actually accepts it.

She then tried to work some magic and since we had already been downgraded to economy, she was able to book us a flight with a layover that would get us in earlier but with a different airline. Again no seat assignment and would get it at the gate.

When it came time, we headed to the airport for our new flight, on a different airline and got there early for our seats. We checked out of the hotel and once we got to the airport, we got the credit card notification. They charged our card.

Luckily, this was one dilemma easily fixed with a quick phone call. Within a few minutes, they got that squared away and took it from the voucher.

So now we’re at the gate and lucky for us again, we got seats across the aisle from each other. It was finally looking up...or so we thought.

Another Cancelled Flight

We’re boarded, headphones playing music, thinking about our hour layover at the next destination when they announced a luggage and weight problem. We started getting a little anxious because of the short layover but still thought ”okay we got this”.

Nope, we indeed did not “got this”. Instead, we sat on a plane at the gate for an hour and knew any hopes of making the other flight were out the window. 

But the layover ended up being a moot point because a few minutes later we got the news that everyone had to deboard...the flight was being cancelled. Something with mechanical and cargo issues.

Taking Matters into Our Own Hands

At this point, Phil had enough and booked a direct flight through yet another airline, but one that we had more faith in *Cough* Delta *Cough*. It sucks having to pay big money for a day of the flight, but at some point, we were missing work every day and were running out of options.

Now we’re working on the refund part (fingers crossed) but are happy to report we finally made it to our destination with only having to call off one day of work. Still not great but it definitely could have been worse.

Life Lessons Learned from a Cancelled Flight

We like to always have a silver lining from bad situations, or at the least, a life lesson takeaway. Obviously, a cancelled flight is completely out of your control but we did learn a few tidbits.

Fly Out Early in the Day

This was one of the later flights we’ve taken in a while. We try to fly out first thing in the morning and in this scenario, earlier would have been better.

One of the reasons the choices were so limited was the lack of flights for the rest of the day. It was already late so there was no hopping on another flight real quick.

Ask About a Different Airline

Getting on another airlines flight was the only reason we even made it to work by the end of the week. And it took not one, but two trips to the airline front desk to make this happen.

Looking back, the moment we were told the next available flight was in two days we should have said....umm no. Because that was the next available flight for their airline only.

Other airlines did have open flights leaving earlier which helped us only miss one day of work instead of two days. Getting on another airline was clutch.

Ask for Vouchers

If we wouldn't have asked for the hotel voucher, they were not going to give one. It kind of seemed more like a “don’t offer unless you have to” situation. 

We’re glad that at least one thing we were on top of and made sure we had something. Just remember to double-check the vouchers are used and not your credit card.

Ask About Worst Case Scenario

You should hope for the best but expect the worst. As soon as the one front desk stated “all the hotel restaurants, restaurants nearby and airport restaurants accept the meal voucher” we should have immediately asked…'' but what happens if they don't. 

We’re not saying he lied on purpose, maybe he just didn’t know but the truth was that no one accepted the meal voucher. This way, we would have at least been more prepared or would have tried negotiating for something else.

Be Prepared to Fight for Reimbursement on the Back End

In a perfect world, we would have gotten a reimbursement right away for the seat downgrade. Or at the very least, a guess on what the value would be. Airlines just aren’t working like that.

It’s almost a “get through the flight then we’ll talk” scenario. It sucks but it's out of your hands so worrying about it won't help anything.

Just make sure to take notes on everything so you can construct a very good, thorough message once you submit the final request.

Cushion More Days Around a Trip

This might not always be doable, but if it is, schedule off days before your main event and before your next commitment. If we didn’t have a schedule already filled up at work, this whole scenario would have been a lot easier. We always cushion one day before and one day after, but this time, it wasn’t enough.

If we can, we will probably start trying for a 2-day cushion in our travel plans for before and after. This way if nothing goes awry, we get some downtime to rest. If it also goes to h-e- double hockey sticks, we’re still good.

It won’t be the Last Cancelled Flight in Our Lifetime

We travel so much, we know this scenario, as crazy as it was, will not be a one and only. Cancelled flights happen all the time and there is so much out of your control.

So if it happens to you, breathe and just do whatever you can that's in your control. Try to always be prepared but know that all the planning in the world still can’t prevent everything.