A Holiday Vacation to Both Coasts — Reader Success Story

Nov 7, 2017

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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 points and miles have helped them get where they want to go. Each week I pick one that catches my eye and post it for everybody to enjoy. If you’re interested in sharing your own award travel success story, email it to info@thepointsguy.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!

Today I want to share a story from TPG reader Molly, who used points and miles to save thousands of dollars on holiday travel plans. Here’s what she had to say:

My boyfriend’s family lives in New York and my family lives in Los Angeles, which is great when we’re vacationing on either coast, but it makes splitting holidays complicated. This year we’re spending Christmas with his family and New Year’s with my family. We live in the Midwest, so we needed to book holiday travel to both coasts without spending a fortune.

Lucky for us I’m an avid TPG reader, and my work travel has helped us rack up a variety of points. Our ideal flights cost almost $1,400 per person, so we had to get creative. We adjusted flight times, looked at nearby airports, and booked awards with a few different programs to make it work.

Non-stop flights from Madison to New York the Friday before Christmas were going for $550, but we found an early Saturday flight on Southwest from Milwaukee to LaGuardia for just 7,219 points each. We didn’t have any Rapid Rewards points banked, so we transferred from Chase Ultimate Rewards to Southwest and were able to book instantly.

We’ll be traveling with two sets of golf clubs, so the free checked bags on Southwest are a nice perk. Also, we’ll use the anniversary free night certificate from our our Marriott credit card to stay at a Category 4 hotel by the airport so we can get a good rest before our early flight.

Our optimal flight from JFK to LAX was the day after Christmas at a cost of $489 or 56,000 SkyMiles per person. But if we flew Christmas night instead, the same flight cost only 20,813 points when we booked through Chase. This was our first time using the Ultimate Rewards travel portal, and it made sense because we’d rather earn SkyMiles and MQMs for the flight than redeem them at less than 1 cent per mile.

I also have the Platinum Card from American Express, so we’ll be able to access my favorite Sky Club (and the SkyDeck!) at JFK. Since it’s December, we’ll also get a $30 Uber credit that will help offset our transportation costs in the city.

For our last leg (LAX back to MSN) we chose a red-eye on United to extend our vacation time and save a little money. The flight we chose cost $297 or 19,786 points per person through the Chase portal. However, I was feeling low on Chase points, and we were determined to spend as little “real” money as possible. The same flight cost 25,000 United miles, and we decided it was worth saving our Ultimate Rewards and using the stray MileagePlus miles we had from various work trips.

Holiday travel can be expensive, but by traveling on points and miles we saved nearly $3,000. We didn’t book any flash sales or score any cheap first class tickets, but we were able to visit both our families for a fraction of the normal cost. Sometimes you have to fly during peak times (like the holidays!), and while you may not find many bargains, you can use points and miles to get where you’re going on a budget. Thanks TPG!

The Delta SkyDeck at JFK is a great spot for avgeeking before (or after) a flight.

When you’re evaluating different award options, the one that requires the fewest points isn’t necessarily the cheapest. Molly and her boyfriend used nominally more rewards by booking their flights home through United, but points and miles are not all created equal. Ultimate Rewards points are highly valuable and they don’t expire, so even though those tickets won’t be eligible to earn miles or elite credits, redeeming roughly 25% more MileagePlus miles was the better deal.

If you want to book awards during peak travel times, it helps to have a flexible schedule. Even when you plan a trip far in advance, award availability may be limited around major holidays. Your odds of finding space improve if you’re willing to fly at undesirable times (like very early morning) or on an actual holiday. You can augment this strategy with airline elite status that lets you alter your itinerary without penalty, or by flying a carrier like Southwest that has no change or cancellation fees. Book a flight that works, and then switch to a better one when the opportunity arises.

I love this story and I want to hear more like it! To thank Molly for sharing her experience (and for allowing me to post it online), I’m sending her a $200 airline 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 at the top of this post). Feel free to also submit stories of your most egregious travel mistakes. In either case, 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 by Astrid Riecken via Getty Images.

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  • Earn 80,000 bonus points after you spend $5,000 on purchases in the first 3 months from account opening. That's $1,000 toward travel when you redeem through Chase Ultimate Rewards®
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