Should I Buy Trip Insurance from My Airline During Checkout?

Dec 21, 2014

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TPG reader Cathy tweeted me to ask:

@thepointsguy– “Is it ever worth purchasing the trip insurance that airlines offer during checkout when buying a flight?”

Trip insurance is a tricky subject. I think the main thing to know is the distinction between Trip Protection—which is usually what’s offered when you check out while purchasing a flight on an airline website—and Trip Insurance.

Trip insurance is a lot meatier, offering a lot more protection for your trip. Travel or trip protection is more difficult to categorize, and while there could be some good policies, in general you’ll probably end up paying more when you’re checking out and buying a flight than if you shopped around after the fact.

Is buying trip insurance worth it? Photo courtesy of Shutterstock.
Is buying trip insurance worth it? Photo courtesy of Shutterstock.

It could make sense to purchase during the checkout process, but I recommend looking carefully through each policy to see the finer details before making a decision. I’m pretty comfortable saying that most of the time when you check out to buy your flight, they’re banking on the fact that you don’t want to lose the fare by taking the time to read through the whole policy. If you take 20 minutes to read through the policy, more than likely your session will time out and you’ll have to start over, which puts you at risk of losing that fare or ticket.

If you really want to buy trip insurance, I would recommend visiting the Insure My Trip website. You can probably find something for the same price or less that gives you better coverage. It pays to shop around, and you can usually add a policy after you purchase a flight, so there’s no rush to buy the insurance immediately. Of course, make sure you take the time to fully understand what you’re buying, because it can be a real problem if you pay for something and later realize it doesn’t provide the coverage you need.

For more info, check out these posts:

If you have any other questions, please tweet me @thepointsguy, message me on Facebook, or send me an email at

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