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One of the things I love most about being The Points Guy is getting to hear stories from readers about how award travel has affected their lives — the exotic vacations they’ve planned, the trips they’ve made to be with family and friends, the premium seats and suites they’ve experienced and so much more, all made possible by points and miles. I love to travel and explore, and it’s an honor to be able to help so many of you get where you want to go.
I like to share these success stories to help inspire you the way you inspire me! From time to time I pick one that catches my eye and post it for everybody to enjoy. If you’re interested in sharing your own story, email it to email@example.com; be sure to include details about how you earned and redeemed your rewards, and put “Reader Success Story” in the subject line. If we publish it, I’ll send you a gift to jump-start your next adventure!
Recently, I posted a success story from Meghan, who salvaged a family vacation after a booking error. Today, I want to share a story from TPG reader Matthew, who used points and miles to stay on course during irregular operations. Here’s what he had to say:
TPG always talks about the benefits of transferable points, and since Southwest is the airline I use most, I decided to focus on earning Chase Ultimate Rewards. I booked some big awards recently — including a honeymoon trip to St. John in April with my fiancé Karen — so I didn’t have a ton of points saved up. However, the 33,000 points I did have went a long way toward saving us from a giant headache earlier this year.
My brother plays college football, and had a game in New York the weekend before Halloween. I travel to most of his away games, and since this one was in New York and Karen had never been there, I thought it would be fun to take a couple days and enjoy Manhattan. We booked a red-eye SAN-JFK for Friday night (using JetBlue points I earned from the Virgin America points match), caught my brother’s game and dinner on Saturday, and hit everything on our must-do tourist checklist on Sunday. It was a great trip, and everything went smoothly until it was time to go home.
We were flying out of Newark on Sunday night, making use of our Southwest Companion Pass. We got to the airport very early to make sure we didn’t miss the flight, since we were on the last Southwest flight of the day to San Diego. We got through security smoothly and were waiting at the gate when we noticed that it had started raining, and I got a notification that our flight was delayed.
We weren’t worried yet; we had a two-hour layover in Denver, so a small delay wouldn’t keep us from making our connection. However, the rain picked up quickly and it was soon a downpour. I’m not sure if it looked worse on Doppler, but suddenly all flights into Newark were diverted. The rain only lasted 30 minutes or so on the ground, but planes were no longer landing. Our half-hour delay turned into an hour, and then two hours, and all the gate agents could tell us was that the plane we were supposed to be boarding had been diverted.
Karen started to stress. She teaches second grade, and had a classroom of kids expecting her to be there for all of the Halloween festivities the next morning. I realized we were unlikely to make our connection in Denver, so I got online and booked the first Southwest flight from Denver to San Diego on Monday morning. Thanks to Southwest’s awesome change/cancellation policy, I knew I could cancel it later if we were somehow able to make it home Sunday night.
That was a nice insurance policy, but it still wouldn’t have gotten Karen to school until after noon, so I kept looking for a better option. Remembering my Ultimate Rewards balance and that United is also a Chase transfer partner, I looked to see if United had any options that could help us get back to San Diego. Incredibly, there was a nonstop EWR-SAN flight scheduled to leave about 90 minutes later, and even better, there was Saver level award space!
I quickly called United to confirm before transferring the points over from Ultimate Rewards. The agent told me that the flight was delayed about 30 minutes, but there was plenty of availability. We were able to book two seats together for 12,500 miles and $5.60 each. Unfortunately, United also charged a $75 close-in booking fee, but it was worthwhile, since otherwise we would have been staying in either Newark or Denver for the night.
We had to take the shuttle between the Southwest and United terminals and go through security again, but that was a breeze since both of us have Global Entry and TSA PreCheck. When we got to our United gate, I cancelled both our original Southwest flight and our recently booked DEN-SAN flight for the next morning, losing no money or points in the process. Our United flight ended up being further delayed (that plane was also diverted during the storm), so our 8:35 departure became a 10:45 departure and a 1:45 am arrival. We were exhausted, but Karen was able to make it to school on time to enjoy Halloween with her class.
While it may not have been absolutely necessary to get home Sunday night, our points made it possible and fairly painless. Those flights would have cost over $1,000, which we wouldn’t have been willing to pay. Instead, we spent 25,000 points and $161 dollars, which was absolutely worth it to us. Thanks to TPG for showing me the tricks of the trade; not only did you inspire the weekend trip to New York, but also you helped us get home on time!
It’s important to act quickly when your flight is delayed or canceled, because whatever alternatives you have might not last long. Gate agents will be swamped by a planeful of passengers, and available seats on other flights may already be claimed if you’re not among the first to be served. You might have luck engaging with airlines on social media, but if you really have somewhere to be, take your travel plans into your own hands.
Matthew smartly considered his options not only on Southwest, but also with other airlines in his travel rewards portfolio. You can often find last-minute award availability that offers great value, since airfare tends to go up steeply close to departure. One airline might have space even though others don’t, so it pays to look around.
Finally, airline elite status can help you avoid some extra charges (like close-in booking fees). Make sure you’re familiar with your benefits so you can put them to work during delays or other irregular operations.
I love this story and I want to hear more like it! To thank Matthew for sharing his experience (and for allowing me to post it online), I’m sending him a $200 Visa gift card to enjoy on future travels, and I’d like to do the same for you.
Again, if the strategies you’ve learned here have helped you fly in first class, score an amazing suite, reach a far-flung destination or even just save a few dollars, please indulge me and the whole TPG team by emailing us with your own success stories (see instructions above). You’ll have our utmost appreciation, along with some extra spending money for your next trip.
Safe and happy travels to all, and I look forward to hearing from you!
Featured image courtesy of Jan-Stefan Knick via Getty Images.
NEW INCREASED OFFER: 60,000 Points
TPG'S BONUS VALUATION*: $1,200
CARD HIGHLIGHTS: 2X points on all travel and dining, points transferrable to over a dozen travel partners
*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.
- Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $750 toward travel when you redeem through Chase Ultimate Rewards®
- 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
- Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards. For example, 60,000 points are worth $750 toward travel
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