This Credit Card Perk Scored Me a $500 Free Vacation After My Flight Was Delayed

It was my last day of vacation in New York City. I was taking a final ride on the Staten Island Ferry when my phone buzzed with a text from American Airlines. I froze. My flight had been canceled because of inclement weather. This must be a mistake, I thought, looking around. 

The skies were clear. It was only a few hours before my flight and I was just about to leave for the airport. Instead, I called American Airlines.

For some, an unplanned overnight delay in one of the most expensive cities in the world would be a major headache. But as a personal finance writer who loves testing out money hacks, I was also curious about a credit card perk I'd never used before. I booked my flight with my Chase Sapphire Preferred® Card*, which comes with a trip delay reimbursement perk.

On the other end of the line, the customer service representative confirmed the flight delay and I soon received another text inviting me to rebook my flight for the next day. A few hours later, rain started pouring -- just as the airline had predicted.

Dear reader, believe me when I tell you -- I was excited.

Read more: Don't Sleep on the Chase Sapphire Preferred's 100K Point Bonus. Here's How I'd Use It

What to know about the Chase Sapphire Preferred's trip delay reimbursement

Some of the best features of the $95-annual-fee Chase Sapphire Preferred Card are its travel protections. 

They include trip cancellation/interruption insurance, lost luggage reimbursement, baggage delay insurance, travel accident insurance, auto rental coverage and trip delay reimbursement -- the benefit I used on this trip.

If your (or another covered traveler's) common carrier travel is delayed for more than 12 hours or requires an overnight stay for a covered reason, Chase will reimburse you for up to $500 of reasonable expenses (per covered traveler, per trip) incurred during the delay that isn't reimbursed by your airline or other travel insurance policies.

According to the terms and conditions, "covered reasons" are equipment failure, inclement weather, strike or hijacking/skyjacking. "Reasonable expenses" include meals, lodging, toiletries and medication. The coverage begins on your trip departure date and ends on your trip completion date.

To activate this benefit and the Preferred's other travel protections, you simply need to pay for your ticket with your card. Oh, and be sure to keep all your receipts -- you'll need them when it's time to file your claim.

How I Used my Chase Sapphire Preferred to fund a bonus NYC vacation

After confirming with the airline that my flight was really canceled, I carefully read the terms and conditions of the trip delay reimbursement benefit. Then I called Chase customer service to confirm a few things I wasn't sure about.

First, I wonder if my situation was a covered delay. Because my flight was canceled and rebooked to a different one, I wasn't sure if this was technically a "delay." (Spoiler: it was.)

Second, what constituted a "reasonable" expense for food? The customer service representative suggested a $50 limit per meal. (Easy enough.)

Third, was I eligible for coverage even though I'd booked the flight with airline miles and only paid the taxes and fees with my Sapphire Preferred card? (Again, no snags here.)

With my questions answered, it was time to treat myself -- "reasonably" -- on Chase's dime.

I booked a hostel bunk for about $75 a night and then headed to dinner, where I splurged on a sashimi platter, drink and dessert. At around $48 after taxes and tip, it was the most expensive meal I'd had in a while. But hey, it was delicious, and Chase was paying, which made it taste all the better.

I finished my evening with a lovely stroll in Central Park. At this point, I was feeling pretty good. Without needing to worry about the extra costs, the delay felt like less of an inconvenience and more like a bonus vacation.

The next morning, I grabbed breakfast at a local bagel shop for $17 and headed for the airport.

Everything went smoothly until rain clouds started rolling in while the plane was on the tarmac. We were told takeoff would be delayed by a half-hour, then another half-hour, and so on and so forth, until they finally canceled the flight several hours later. When I received the link to rebook, the first available flight was two days later. I was stuck in New York for another two nights.

After retrieving my luggage from the chaotic mess at baggage claim, I treated myself to a fancy poke bowl ($21) as consolation.

With no flight the next day, I explored downtown New York and stopped by a taco place for a delicious lunch -- $23. It was a lovely time, but I was now nearing my trip delay reimbursement's $500 limit and starting to miss home.

Thankfully, the skies were clear the next day. My flight took off without issue and I could finally leave New York -- three days after I was supposed to.

Filing the claim

Once I returned home, I started filing the claim through chasecardbenefits.com. I filled out a form with the following information:

• Traveler's name and information
• The date of the original flight and the date of delay
• The ticket purchase date of the original flight
• The amount of reimbursement I was claiming
• The amount of reimbursement I received from the carrier or other insurance policies
• The reason for the flight delay

I also uploaded the following documentation:

• The ticket for my original flight
• The itineraries of my original flight as well as the subsequent rebookings
• My credit card statement showing I'd paid the taxes and fees for my flight with my Chase Sapphire Preferred card
• Receipts for all the expenses I was requesting reimbursement for

The whole process was very intuitive. Chase's portal provided clear instructions about the information and documentation needed and where to put it. Organizing my documents, totaling my expenses and filling out the claims form took me about an hour.

But Chase needed some extra convincing

Eight days later, I received an email asking for additional documentation. Chase wanted a statement from the airline regarding the length and reason for the delay. I contacted American Airlines and received an official letter via email a few days later, which I uploaded to the claims portal.

They also wanted proof that I'd charged my original ticket to my Chase Sapphire Preferred. I'd already provided my credit card statement when filing my original claim, but I think there was some confusion due to how I originally booked my flight.

I'd booked an American Airlines flight on the Qantas website, one of American Airlines's alliance partners, using Qantas loyalty points through a process known as codeshare booking. 

My original ticket was issued by Qantas, and my credit card statement showed a payment (for taxes and fees) made to Qantas. But the actual flight was operated by American Airlines and all the documentation relating to the delay came from American Airlines. 

So it seemed like the flight I partially paid for with my Sapphire Preferred and the flight that was delayed were two different flights. I uploaded all the relevant documentation again to the portal, along with a brief note about how codeshare flights worked.

Ten days after submitting the additional documentation, I got an email saying my claim had been approved and asking how I'd like to receive my reimbursement. After double-checking that the email was legitimate, I chose direct deposit and filled out a form with my bank information.

I received the money two days later for the requested reimbursement. The total, which covered all my food, lodging and transportation expenses during the delay, came out to about $380 -- more than enough to make up for the card's $95 annual fee.

Tips for maximizing credit card travel insurance

The claims process was relatively smooth but I still learned some lessons along the way. If you ever need to use your credit card's travel insurance benefits, here are some of my tips:

• Read the terms and conditions before doing anything. Carefully read the terms and conditions of your credit card's benefits guide to know what situations are covered under your card's travel protections, what the limits are and what documentation is needed. If you're unsure about anything like I was, call your credit card issuer or travel insurance provider for clarification before spending any money.
• Don't use up your allowance too quickly in case you're delayed longer than expected. Looking back, I'm glad I booked a cheaper hostel instead of a hotel. When my first flight was canceled, I had no idea that the delay would last three days. If I'd booked a hotel at New York City prices, I probably would've exceeded the $500 reimbursement limit and ended up with out-of-pocket costs.
• Organize your documentation as you go. Every time I paid for a reimbursable expense during my trip delay, I immediately took a photo or screenshot of the receipt and kept it in a dedicated folder on my phone. I also took screenshots of every communication the airline sent me, plus screenshots of my flight status page every time there was an update or a new delay. Organizing my documentation as I went made things so much easier when it came time to file my claim. 
• Have an emergency fund. Even if trip delay insurance will reimburse you for expenses, there will be a delay between paying for those expenses and getting your money back. I recommend building some buffer room into your budget when traveling or having an emergency fund so you can pay for any unexpected costs without going into debt if your reimbursement takes a while.

Final thoughts

I've always liked the Chase Sapphire Preferred for its good rewards rates and transfer partners but this experience taught me just how valuable its travel protections can be.

While I would never actively wish for something to go wrong just so I could test out the card's travel insurance, knowing that those protections are there gives me extra peace of mind whenever I travel -- and saves me a lot of stress and money when things do go wrong.

*All information about the Chase Sapphire Preferred Card has been collected independently by CNET and has not been reviewed by the issuer.