Why I Went With The Most Expensive Award Option On My Recent Flight Booking

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The Lowest Priced Award Is Not Always The Best Option For You

Today I come before you humbly so that you can all laugh at my mistake.  See on my recent award booking I decided to go with the most expensive booking option, at more than 45% an increase in cost. I did this knowingly…because it simply made too much sense to me! In all seriousness I thought I would show you a recent award booking I made and why I decided to go the route I went. Even if many would consider it the worst option I will break down my thought process for you. My point is, the lowest priced award is not always the best.

The Last Frontier, Here We Come

I was looking for some topics for the website when I came across some new direct routes to Alaska. And wouldn’t you know it that Detroit was one of the airports on the list.  This sent me down a rabbit hole of sorts.  I have always wanted to check out the last frontier and what could be better than doing it direct?  My son has not flown with me in over a year, and as I have said in the past traveling is one of the few things we have in common.  It has been a big piece of our relationship missing and this seemed like the perfect chance to correct that.

Off I went searching flights, still not sure if it would happen or not. After talking with my wife she said go for it and that she was not interested in tagging along with my daughter.  So boys trip it was!  And since this is our first trip since the pandemic, I am sitting on a stash of miles and the flight takes as long as getting to Europe I figured we would do it in style. Domestic first class here we come!  Can we get some lie flat on this luxury route already 🤣?

Lowest Priced Award Is Not Always The Best

Booking Options

I knew I wanted to fly Delta since they offered the direct flight.  I am also chasing Delta status, as you may know from my recent application spree.  So my plan was to book my flight with cash and his with award redemption(s).  I was going to use my Amex airline incidental credits to cover a lot of my cost but I needed to find some award space for him.

The options I were considering were Delta Skymiles, Virgin Atlantic Miles & Flying Blue / Air France. I had a stash of Virgin Atlantic miles from covid cancellations and Delta Skymiles for the same reason. My Flying Blue account is at a big fat zero but I could easily transfer some in if needed.

I found some saver first class space and here is how the pricing shook out:

Flying Blue

Lowest Priced Award Is Not Always The Best

Delta Skymiles

Lowest Priced Award Is Not Always The Best

Virgin Atlantic
Lowest Priced Award Is Not Always The Best

These prices are not all for the exact same flight but Flying Blue and Delta were the same for either flight.  Since Virgin Atlantic is a segment based program, like British Airways Avios, adding a connection made the price astronomically high.  So Virgin was only a consideration for the direct flight out.

The direct flights out of Detroit are only available on Friday and Saturday and since we were not staying an entire week we had to book a connecting flight on the way home.

The cash price of the flights was just under $600 each way so we will use that as our baseline for our valuations.

  • Flying Blue
    • $600 – $32.07 = $567.93 / 36,000 = 1.57 cents per mile
  • Delta
    • $600 – $5.60 = $594.40 / 45,000 = 1.32 cents per mile
  • Virgin Atlantic
    • $600 – $5.60 = $594.40 / 52,500 = 1.13 cents per mile

As you can see, domestic first class is not a huge win most of the time, even on trips to Alaska.

Which Option Did I End Up Taking & Why?

I guess I already spoiled the ending since you know I went with the expensive option for part of it.  I ended up using Virgin Atlantic miles for the direct flight there and Delta Skymiles for the flight home for him.  That is because Virgin Atlantic shot up in price with the connection in Minneapolis on the return flight.

But why would I take the two least valuable options? Especially when most people would value Virgin Atlantic miles above 1.13 cents a piece?


Virgin Atlantic Reasoning

If I was booking this flight last year it would have cost me 22,500 miles for the direct flight. With Virgin’s recent program changes, going distance based, the cost for flights like these have shot up.  There is still value to Europe (for the time being) but who knows if that will be around by the time we can use it.  Throw in the fact that Delta saver space is becoming harder and hard to find on Virgin Atlantic, even domestically, and I wanted out of this sinking ship. Because of that cent per point valuations didn’t mean a ton to me and I am sitting on a decent stockpile of their miles from my cancellations.  I’ll get what I can, while I can and move on.  Could I get more if I waited? Probably, but these are 3rd tier miles to me now and the pain of using them is a lot less than it used to be.

Lowest Priced Award Is Not Always The Best

Delta Skymiles Reasoning

While most people would value Virgin Atlantic miles above 1.13 cents I don’t think people would look down on 1.32 cents per Delta Skymile.  I personally peg them at around 1.25 cents a piece and with Delta that value is usually fast approaching a devaluation.  So even though the cost was 9,000 more miles than Flying Blue it was still a good value for my Skymiles.  I had a little stash of Delta Skymiles as well and 80,000 more are on the way from my new Delta Reserve card.  So it made sense and I wouldn’t need to transfer anything to make the booking.

Flying Blue awards

Why Not Flying Blue?

Why not grab the best deal all the time, every time?  The main reason is because I didn’t have any Flying Blue miles in my account already.  If I had 100K in all 3 accounts then I would be singing a different tune right now.  But, since this booking would have taken a transfer I decided against it.

  • First, my transferrable currency balance is on the mend and I would prefer to use miles I already have. Plus, getting 1.57 cents doesn’t move the needle enough to make me dump some.
  • Second, I was still getting get value out of my Delta Skymiles.
  • Third, I want to dump my Virgin Atlantic stock ASAP as long as it is within reason.

Those three things add up to Flying Blue, and it’s best value redemption, being left out in the cold.

Lowest Priced Award Is Not Always The Best – Final Thoughts

As you can see, using the miles with the best value doesn’t always make the most sense, at least for me.  Hopefully this helps you consider all aspects of your miles and points during your next booking.  Cent per point isn’t the only thing you should be considering.

What do you think?  Would you have booked it the same way or done something different? Let me know below!

Mark Ostermann
Mark Ostermann is a father, husband and miles/points fanatic. He left the corporate world after starting a family in order to be a stay at home dad. Mark is constantly looking at ways to save money and stay within budget while also taking awesome vacations with his family. When he isn't caring for his family or taking a weekend trip, Mark is working towards his goal of visiting every Major League Baseball ballpark.

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  1. Having orphaned miles is a major consideration for me as I am going to be booking award travel to Asia for a trip next March that includes a long cruise.
    I could transfer my valuable UR points to Singapore Airlines (would love to take the 18+ nonstop from EWR!) but if anything causes the cruise itinerary to be drastically altered, or there are other travel restrictions that might lead to a change in itinerary, overall trip plans or outright cancellation (possibly by us), I don’t want the bulk of my points held there. So I will only look at options using UA or AA miles, which will be much easier for me to continue to use in the future.

  2. in a semi-similar situation. Have 240k Delta miles from a cancelled 2020 itinerary. Now looking at booking one ways from Mexico City to Buenos Aires in Feb 2022- Delta wants 77.5k pp to book the Aeromexico flight & Aeromexico wants 75k of their points for the same flight (there has to be a joke in there about pesos somewhere…). HOWEVER, MR transfer to Aeromexico at 1:1.6, so it would only be 47k MR pp transferred in from Amex to book the tickets. Even though the MR balance is almost 7 figures it just doesn’t make sense for the possibility to have yet more points trapped/orphaned from flights that may never happen.
    Also, have 180k orphaned VS miles & keep almost converting to Hilton but then backing off. I’ll definitely use Hilton points eventually & those VS miles are probably DOA, but still…
    Also, please keep using ‘direct’ instead of non-stop. Thanks.

    • Haha I do sometimes sub in non-stop there 🙁

      So many things to consider these days that we normally didn’t think about in the past.

  3. Nice article – I often go with more expensive to get better times and also consider whether I will ever have an opportunity to use the miles again or often enough – not all redemptions have to be optimal for sure!

  4. Mark,

    Great write up and you will love Alaska.

    One pet peeve of mine – please quit using “direct” for the flight from Detroit to Anchorage. It is non-stop. I assume you know the difference and that they do mean different things in the airline industry.



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