Award obsessions: from poor value to a great find, our updated sweet spots, and more


Do you obsess over your award bookings, wondering if you’ve eked every last thousandth of a cent out of your redemption? Don’t worry, we do so you don’t have to. This week in FM on the Air, see us talk about our own award anxiety and how it is affecting our #40Kfaraway obsessions, which cards we’re using at Simon Malls for those $1K cards, and more.

For those who would rather listen during the morning commute or while you’re working, the audio of our weekly Facebook Live broadcast is also available for download as a podcast. However, due to issues with the audio in this week’s file, there is no addition to our podcasts this week at this time (if we get that audio sorted out, hopefully we’ll eventually add this week’s to the list, so check back).



Google Play:

On to our weekend recap of the week’s top stories:

In award booking

How to book the cheapest flights with Chase Ultimate Rewards

Good luck with this, Greg

This week’s big find in award booking is without a doubt the fact that Greg discovered how to book (just about) any flight through Chase Ultimate Rewards at a value of 1.5c each. This is huge because many of the (cheapest) low-cost carriers around the world do not show up in the Chase portal or in some cases the portal does not show the cheapest fare classes. This means no longer needing to choose between paying cash or getting poorer value in those situations and it means that maybe I should be afraid after all.

Redemption remorse: Great deal or terrible mistake?

Speaking of being afraid, have you ever redeemed your rewards only to feel afraid that you didn’t use them to get the best value you could? I recently had just that experience when I redeemed Capital One “miles” for a Marriott gift card. I was able to redeem points that used to only buy $642 worth of travel for a $900 Marriott gift card that I will put to use for nearly face value. That sounds like a huge win, but I second-guessed it, recognizing my potential opportunity cost. See this post and tell me whether I did well enough to be satisfied or I should have done things differently.

A sweet spot hotel….and a rookie mistake

From the Hotel Napa Valley website

This just wasn’t my week for award redemptions…..or maybe it was? I stumbled on what immediately felt like a fantastic find: a beautiful place to stay in Napa for a few nights that charges just 12K per night — even for a 2-bedroom suite. If that sounds great to you, maybe you’ll understand why I leapt before I looked. As you can imagine from the title, I later realized that putting the cart before the horse meant a failure to maximize my resources. In this case, there is no question: I wasted valuable points at much less value than what they could have gotten me. Yeah, I’m saving a bunch of money on my room, but it cost me a business class ticket to Europe that I could have kept for a couple hundred bucks. See how I screwed up so you don’t have to.

On my mind (award anxiety edition)

If you, too, obsess over your award bookings and re-think those redemptions like I do, take solace in the fact that you and I are not alone. In a development that should surprise no one, Greg developed a formula to figure out whether or not your redemption makes sense. Warning: as you’ll see us discuss in the video above, there comes a point where analysis paralysis and Monday morning quarterbacking can start to suck away the joy of free. But as we argue above, it’s worth considering this stuff if you’re in a spot where you’ll need to replenish the points you’ve put to use.

Updated resources

This week, we also made updates to several key resources pages.

First up, our sweet spot series was missing the best values for Australia, New Zealand, and Oceania. If you’re wanting to get Down Under, you’ll want to lo look up the best values in each of the major transferable currencies. To help you do it faster and more efficiently, we’ve also added a handy table of contents near the top of the following updated posts:

Amex Membership Rewards sweet spots
Chase Ultimate Rewards sweet spots
Citi ThankYou sweet spots

This week also saw what appears to be the final death of gift cards that triggered Amex airline fee credits. Since you’ll most likely no longer be able to buy gift cards to trigger those credits, we’ve updated our guide to what still works for each of your airline options as of July 2019. See the updated guide here:

Amex airline fee reimbursements: What still works?

And that’s it for this week at Frequent Miler. Check back soon for our week in review around the web and this week’s last chance deals.

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