I had plenty of time to take pictures of Chicago as we circled it for over an hour.
Photo: Shep McAllister

We’ve talked about how using a credit card with good trip delay insurance, like the Chase Sapphire Reserve or Chase Sapphire Preferred card, can be palliative when things go awry in the airport, but a recent, nightmarish travel experience stretched my own perception of what this benefit can be used for.


Never connect in Chicago
Screenshot: Shep McAllister

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In preparation for an upcoming move to Columbus, Ohio, my wife and I recently flew up to spend a long weekend seeing the city and looking at options for housing. But weather in Chicago (it’s always weather in Chicago) forced our plane to circle Lake Michigan for an hour before eventually diverting to Indianapolis, where we sat on the tarmac for 90 minutes until a gate finally opened for us. By then, it was already after midnight, and needless to say, we were not going to make our connection.

Normally, this would mean a night in an airport hotel, and some rebooked itinerary the following day. And since I’d booked this trip with my Chase Sapphire Reserve, this situation would obviously call for us filing a trip delay insurance claim to recoup our expenses. But we had an important appointment with our realtor the following morning, and with no direct flights between Indianapolis and Columbus, it was clear that the only way we were going to make it in time was to rent a car that night, and drive the three hours to Columbus ourselves.

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Here’s how Chase, in part, describes its Sapphire Reserve trip delay insurance:

If your common carrier travel is delayed more than 6 hours or requires an overnight stay, you and your family are covered for unreimbursed expenses, such as meals and lodging, up to $500 per ticket.

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The Sapphire Preferred has essentially the same benefit, but with a 12 hour requirement.

Would renting a car and driving through the night qualify as an “overnight stay?” Clearly, our flight into Columbus was going to be delayed more than six hours, though since we voluntarily left the airport without getting rebooked on another flight, we didn’t technically have a new itinerary to prove this. Nothing in the fine print explicitly mentions car rental expenses, and while we thought that our delay was in keeping with the spirit of trip delay reimbursement, insurance companies aren’t known as appreciators of nuance and gray ares.

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To ratchet up the pressure, I forgot to put gas in the car when we returned it the next (same?) morning (operating on less than three hours of sleep will do that), and ended up paying a roughly $90 fuel surcharge.

But after a few weeks of back and forth with the same insurance company I detailed here, plus some help from Southwest Airlines in providing the necessary documentation, my claim of over $180 was approved and paid out.

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It’s possible I got assigned a lenient insurance agent, and you should by no means take this as a guarantee that your similar claim will go through. But it was a great feeling to get reimbursed for an emergency car rental that I was going to pay for regardless. Better yet, the only part of the trip that I’d put on my Sapphire Reserve was $11.20 in taxes and fees, since I booked the flights with points, but that was all it took to be eligible for this benefit.

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This reimbursement, plus my $300 annual travel credit combined to more than cover the card’s $450 annual fee for the year, and that’s not even accounting for the Reserve’s other benefits like primary rental car insurance, which was nice to have while struggling to stay awake on a dark, Midwestern highway at 3 a.m.

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