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Today I want to share a story from TPG reader Allan, who used some creative point transfers to save on a ski trip to Aspen. Here’s what he had to say:

I’ve read your advice not to transfer points speculatively to take advantage of a transfer bonus, since you run the risk of not finding award space or (even worse) getting caught up in a devaluation. But I recently decided to take that risk twice, and I earned a huge payoff in both cases.

First, I speculatively transferred Membership Rewards points to British Airways during the last 40% transfer bonus, figuring I could use them for a future trip to Hawaii or Aspen. I ended up booking a New Year’s Eve trip to Aspen for my family of four using Avios. Cash fares at the time were $545 from Los Angeles, but we paid 15,000 points per person instead, giving me a redemption value of over 3.4 cents per Avios or over 4.8 cents per Membership Rewards point.

I normally stay at Wyndham properties since many of their resorts feature a full kitchen, and Wyndham has a property in Aspen called the Aspen Meadows Resort. Nightly rates over New Year’s week average $700, so Wyndham’s fixed redemption level of 15,000 points per night results in a redemption value of 4.6 cents per point. I didn’t have enough points to book our stay, but during my research I came across the exchange feature on Points.com and saw an opportunity to top off my Wyndham account.

First, I exchanged 25,754 JetBlue points (leftover from a credit card bonus) for 19,316 La Quinta Returns points, which can be combined with Wyndham Rewards at a 1:1 ratio. Next, I transferred 20,000 Starpoints to Aeroplan, giving me 25,000 miles after the 5,000-mile bonus. I then exchanged those miles through Points.com for 21,249 La Quinta points, which I again combined with my Wyndham Rewards, giving me a little over 40,000 extra points to put toward our stay in Aspen. Completing the exchanges and booking the room took 12 days.

The points I transferred were worth about $875 based on your valuations, but they were worth almost $1,900 to me by redeeming through Wyndham. With the delays in transferring and exchanging points among the different loyalty programs, this award redemption was full of speculation and risk, but in the end that risk helped make our $5,000 ski trip happen.

Transfer bonuses (like the ones Amex is currently offering for JetBlue and Virgin Atlantic) are a great way to boost your frequent flyer accounts. I think transferring speculatively during a bonus is fine so long as you’re sending points to a program you either use regularly or think you’ll use in the near future. Allan’s plans may not have been concrete when he made the transfer, but he at least had an inkling of how he would use his Avios. What you don’t want to do is jump on a transfer bonus with no plan to redeem those extra miles, since you may end up missing other opportunities or losing your rewards altogether if they sit idle for too long.

There’s a lot of conventional wisdom in the award travel community, but it shouldn’t be mistaken for inviolable rules. For example, conventional wisdom would generally tell you not to pay to transfer miles between accounts or redeem points for cash, but if it helps you afford a trip to New Zealand or see your favorite team in the World Series, then it may be worthwhile. Points.com tends to offer miserable conversion rates — case in point, swapping Starpoints for Wyndham Rewards isn’t likely to be a profitable move — but the exchange made sense for Allan because he had the opportunity to book such a valuable award.

As he mentions, that opportunity carried significant risk. Award space could have dried up in the time it took for his points to transfer; that wouldn’t have been too problematic since he’s a Wyndham regular anyway, but there are less costly ways to pad your Wyndham Rewards account. Still, so long as you’re aware of the risks and confident you’re getting a good return, don’t be afraid to use your points in a way that goes against the grain.

I love this story and I want to hear more like it! To thank Allan for sharing his experience (and for allowing me to post it online), I’m sending him a $200 airline gift card to enjoy on future travels, and I’d like to do the same for you. Please email your own award travel success stories 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. Feel free to also submit your most woeful travel mistakes. If your story is published in either case, I’ll send you a gift to jump-start your next adventure.

Safe and happy travels to all, and I look forward to hearing from you!

Feature image courtesy of the Wyndham Aspen Meadows Resort

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2018 TPG Award Winner: Mid-Tier Card of the Year
Chase Sapphire Preferred® Card

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.

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More Things to Know
  • 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.
  • No foreign transaction fees
Intro APR on Purchases
N/A
Regular APR
17.99% - 24.99% Variable
Annual Fee
$95
Balance Transfer Fee
Either $5 or 5% of the amount of each transfer, whichever is greater.
Recommended Credit
Excellent/Good

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.