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When flights get cancelled due to mechanical problems or bad weather, it’s easy to descend into a panic. You’re now facing a whole plane full of people in need of rebooking with limited agents and available seats. However, this is the time when it’s most important to remain calm and have a plan. Your actions during this crucial period could make your day much easier or end up costing you hundreds of dollars. TPG reader Jenny wants to know how much of the work she should take into her own hands …

China Airlines is on strike and just cancelled our flight home to JFK on Sunday. Should we sweat getting this rebooked ourselves/right away, or should we wait and let the airline handle it?

TPG READER JENNY

In the event of a cancelled flight, your airline should work to get you to your destination as soon as possible. In certain cases, it may even put you on a competitor’s flight (in this case EVA Air also flies from Taipei to JFK), but there are a few factors that determine whether you should leave it to the airline to reschedule.

There are some times where you simply can’t wait an extra day to get to your destination. Maybe you have an important work event, a family celebration like a wedding or a prepaid cruise or tour you can’t afford to miss. In these cases, you might just want to stomach the costs and book the next available flight yourself. This is where transferable points can be a great insurance policy.

Of course, if your schedule is more flexible (maybe you’re not looking forward to getting back to work after a vacation), you can wait for the airline to find an open seat for you. You might even receive some miles or money as compensation for your delay, and depending on where you are, you might get a “free” extra day of vacation.

What About Travel Insurance?

Don’t overlook the requirements of a card’s travel delay protections if you rebook yourself. (Photo by Isabelle Raphael/The Points Guy)

There are also implications to this rebooking process if you plan to invoke the coverage provided on many top travel rewards credit cards. However, one lesson that I learned the hard way is that if you think you’re going to need to rely these policies, you should always call a benefits administrator and confirm what type of documents they need to process the claim.

Last year I found myself stranded in Hong Kong for 48 hours as typhoon Mangkhut ripped through the city and shut down the airport. My original China Eastern flight back to Shanghai (PVG) was cancelled on Sunday morning, and I was told the earliest I could be rebooked would be late Tuesday night. That didn’t work for me, as I had a young puppy at home that I needed to get back to, so I decided to book my own flight out-of-pocket for Monday afternoon.

I had booked the trip with my Chase Sapphire Reserve, so I called a benefits administrator to ask if my travel insurance would cover the flight I rebooked for myself. I was told emphatically no, but I assumed at the very least that my trip delay insurance would cover the extra hotel night I needed. After all, it was a forced overnight due to a cancelled flight for a covered reason (inclement weather). I flew home Monday afternoon and ended up missing the flight on which China Eastern had rebooked me.

Fast forward a few weeks, and I’ve submitted my claim to Chase for the hotel expenses. They write back asking for proof of rebooking of my original ticket. I reach out to China Eastern who tells me that because I no-showed the flight, there system has no record of it. I try to explain this to Chase, who says that this proof of rebooking is needed to process my claim. I fought back for several rounds and even tried to get Chase to call China Eastern directly, but ultimately my claim was denied and I had to pay for my hotel on top of the flight I’d rebooked for myself.

This was an expensive lesson to learn (nearly $700 total), and it was made even more frustrating by the fact that terms and conditions of the trip delay insurance don’t explicitly ask for this proof of rebooking. Instead, it falls under the catch all last provision from the card’s terms & conditions (warning: PDF link):

Your Account receipt showing that the travel fare was charged to your eligible card. If more than one method of payment was used, include documentation that shows a portion of the purchase was made with your Account.

A copy of the Common Carrier ticket

A copy of Your monthly billing statement (showing the last four [4] digits of the Account number) confirming the Common Carrier ticket was charged to the covered Account. (Only applicable if the travel itinerary does not reflect the last 4 digits of the Account number).

A statement from the Common Carrier indicating the reasons that the Covered Trip was delayed

Copies of itemized receipts for your claimed expenses. For food expenses, receipts are required, however itemized receipts are only required for bills of fifty ($50.00) dollars or more per covered traveler.

Any other documentation deemed necessary, in the Benefit Administrator’s sole discretion, to substantiate the claim.

However, without my original carrier being able to document the delay in getting me to my final destination, I was out of luck. While I knew that I wouldn’t be covered for the flight I booked myself, I didn’t realize that acting to get home faster would prevent me from filing a travel insurance claim.

Bottom Line

Deciding whether to rebook your own flight or wait for the airline to do so boils down to a number of factors, including how flexible your schedule is and how comfortable you are spending money or miles that won’t be reimbursed. Just make sure that in the heat of the moment you don’t do something that will cost you money down the road. If you book your own flight home, make sure to get a copy of your official rebooking from the airline to use in a travel insurance claim.

Thanks for the question, Jenny, and if you’re a TPG reader who’d like us to answer a question of your own, tweet us at @thepointsguy, message us on Facebook or email us at info@thepointsguy.com.

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Editorial Note: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.