How I overpaid by 13,000 points — reader mistake story

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Today, I want to share a story from TPG reader Aaron, who chose an inefficient way to book award flights to Puerto Rico:

My wife and I are new to the points game. Recently, a friend recommended we apply for the Chase Sapphire Reserve for personal spend. We already have a Chase Ink business card (we own our business), although we'd never redeemed the points we earned from it. The Sapphire Reserve was opened in her name, since the Ink card was in mine.

This past summer, we booked a cruise in Puerto Rico to celebrate our fifth anniversary, and I wanted to (finally) use Chase points to cover our round-trip flights from Houston. Although my friend offered to help me redeem them, I decided the Ultimate Rewards travel portal looked simple enough. Thus, I used 76,000 points to book two tickets that would have otherwise cost $475 each. A few days later, I proudly shared my redemption story with my friend, who promptly pointed out my error (two errors, actually).

First, I could have transferred those points to United Airlines and booked the same flights for just 70,000 United points total. Second (and much worse), I used my Ink account to book our tickets, so I only got 1.25 cents per point of value. Apparently, I could have transferred those points to my wife's account and booked the same tickets for only 63,333 points (1.5 cents per point)!

To add insult to injury, we didn't know we needed to bring our Priority Pass card with us during the trip. We "activated" the membership, but didn't realize a physical card would come in the mail, so we were denied access to the lounge in San Juan.

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A crucial step in mastering award travel is learning the various ways to redeem points and miles, and understanding the strengths and weaknesses of each one. That's especially true of transferable points like Chase Ultimate Rewards, which give you abundant redemption options from a single program. You can often get superior redemption value by transferring those points to airline and hotel partners, but when the cost of airfare is low relative to the cost of awards, you may be better off paying cash or redeeming points directly at a fixed rate. In Aaron's case, transferring to United would have been better than booking through his own Ultimate Rewards account, but not as good as redeeming through his wife's account to get 1.5 cents per point.

Aaron may also have been able to surpass that threshold of 1.5 cents per point by transferring to another airline partner. As I write this, Southwest Airlines has ample availability on flights between Houston and San Juan starting at just over 28,000 points per person round-trip. That's about 26% less than what Aaron paid, and about 12% less than redeeming through the Ultimate Rewards portal with the Sapphire Reserve card. Even better, Southwest has round-trip flights from Houston to Fort Lauderdale for just over 5,000 points and $11.20 in fees per person. He could pair that with JetBlue or Spirit Airlines flights between Fort Lauderdale and San Juan for under $150 per person round-trip, and end up paying much less overall (in terms of points and cash combined).

Those itineraries include a stop, so they're not interchangeable with nonstop flights on United, but they illustrate the importance of weighing all your options before you commit to any one booking method. There are many ways to book an award; a great way to learn the game is to seek those ways out and push yourself to find the best deal among them. As for the lounge snafu, the Priority Pass app comes with a virtual membership card that will get you in the door just like the physical card. If you plan to visit a Priority Pass lounge but your card isn't available, the digital version is a handy substitute.

Related: The best ways to use Chase Ultimate Rewards points

I appreciate this story, and I hope it can help other readers avoid making the same mistake. In appreciation for sharing this experience (and for allowing us to post it online), I’m sending Aaron a gift card to enjoy on future travels, and I'd like to do the same for you. Please email your own travel mistake stories to info@thepointsguy.com, and put "Reader Mistake Story" in the subject line. Tell us how things went wrong, and (where applicable) how you made them right. Offer any wisdom you gained from the experience, and explain what the rest of us can do to avoid the same pitfalls.

Feel free to also submit your best travel success stories. If your story is published in either case, I’ll send you a gift to jump-start your next adventure. Due to the volume of submissions, we can't respond to each story individually, but we'll be in touch if yours is selected. I look forward to hearing from you, and until then, I wish you a safe and mistake-free journey!