How Should I Book This? A Look Inside My Own Redemption Process for Beginners

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How Should I Book This? My Award Ticket Redemption Process- Booking NYC to LAS

Award Ticket Redemption Process- Booking NYC to LAS

This is part of my monthly series where I give readers a detailed look at how I go about booking travel based on the different options available and the inventory of miles and points available.

I preach in nearly every article about how flexibility is the key to the miles and points travel game. Flexibility means options and options mean more opportunities to save money and get the best deal.


“I am looking for the best way to book flights for an upcoming trip to Las Vegas. I have a huge stash of Jetblue Points (240,000). 180,000 Delta skymiles. 40K Alaska Miles. 20k Virgin America. I would like to go December 8th-11th or 12th and premium economy is a must, preferably business or first of course.”


When booking award flights, the absolute best advice I can give you, is to be flexible on dates and/or destinations. I also always select “1 Adult” when conducting my searches because the price can go up substantially when choosing 2 tickets, you can always change this later. Since we already know the desired route, we can play around with a few options to see what the best bet is for using our points and miles.

A Good Start

Google Flights

I love to start with a google flights search to see which airlines fly the desired route regularly and get an idea of prices. After plugging our info into Google Flights, I choose “non stop” flights only. (I figure if you’re doing a short trip and want to be in premium seats, you’re not interested in the extra wait and inconvenience of multiple flights.)

Award Ticket Redemption Process- Booking NYC to LAS


Award Ticket Redemption Process- Booking NYC to LAS

As you can see from the calendar view, the exact dates don’t matter much in terms of price difference. But I do need to check one thing first, is that cheap rate an airline I would fly? I choose airlines and uncheck Spirit, because I don’t have any Spirit miles and truthfully, I don’t have a whole lot of interest in flying them for a 6 hour flight. (The older I get, the less inclined I am to do the whole “pre-reclined” seats thing… See what I did there?)

Google Flight’s Search Variations

You’ll notice below that the price jumps up to about $250 RT when the cheaper economy carriers are excluded. However, you’ll also notice there is no significant price difference in dates, which means we can pick a day and go from there, no reason to price out multiple days. Definitive dates can be a huge time saver, so I’m happy to be able to lock those in so early in our research.

Award Ticket Redemption Process- Booking NYC to LAS

After choosing December 8th-12th, the list of flights is shown below along with their starting prices. Keep in mind that this is an economy search because there are ways to upgrade your seats once you find a good award price for a ticket.

Award Ticket Redemption Process- Booking NYC to LAS

Once I have a good idea of round trip prices, I have one more Google Flights search to do. 1 way searches. This way, I will know whether the price for one way is more pricey than the other or whether certain airlines have significant price differences depending on which direction they’re going.

Award Ticket Redemption Process- Booking NYC to LAS

Now looking at one way return prices. Again, no major differences. This is good, we can start at any of our preferred airlines and check out award prices.

Award Ticket Redemption Process- Booking NYC to LAS

Wading Through Our Options

Virgin America Elevate Points

I choose the only non-stop flight that comes up for our day. We can see from the shots above that the Virgin Price for a one way in Main Cabin is either $127 or 5,470 Miles, but what I really like about this search engine is that the Main Cabin Select price is right next to it and the miles required are 10,452. Also, you can see a first class ticket will set you back 33,405 miles. I don’t love spending 33k miles for a one way FC ticket unless I want to burn some miles or it’s considered a transcontinental flight, in which case you’ll be give the true FC treatment. Having said that, Virgin’s First Class from NY to LAS is one of the better I’ve experienced. The seats are not completely flat, but very close and there is a ton of space for each seat.

Award Ticket Redemption Process- Booking NYC to LAS

Award Ticket Redemption Process- Booking NYC to LAS

Let’s Do the Math

Now that we have both a cash price and an award price, we can figure out how much value we’re getting from our miles on the premium main cabin ticket. To do the math divide the cash price (less any taxes or fees you’ll have to pay with the award ticket) by the number of miles required:

  • 229 – 5.60 = $223.40 / 10,452 = .0213 or 2.13 cents per point.

Note: Virgin award ticket prices are revenue based rather than fixed. This means that the number of points needed for an award ticket is based on the cash price of the ticket, so the value of your points shouldn’t vary all that much for different awards. Though you’ll see later, that is not always the case.

Now we have to ask ourselves, is this a good price? Value of miles depends greatly on your specific redemption, but we can get a baseline for value by looking at someone else’s valuation. A quick google search on the value of a Virgin Mile brings me to The Points Guy site, where there is a resource listing mile values that is updated monthly. I look up Virgin Miles and see that they are estimated to be worth 2 Cents each. As long as our redemption value is close or more to the estimated value, I’m comfortable using points for that particular ticket.

Estimated Cost of Miles + Cash

I also find it helpful to figure out the potential value of the miles we’re using. This can be helpful when comparing options since all miles are not equal, it’s nice to have an estimated dollar value. I do this by multiplying the number of miles we’re using by their estimated value and then adding in any out of pocket taxes or fees associated with the award ticket. Let’s take a look:

  • 10,452 x .02 (TPG’s estimated Value) = 209.04 + 5.60 = $214.64

Convert Virgin Points to Alaska Miles

One important thing to remember is that Virgin America is now part of Alaska Airlines and you can currently convert Virgin Miles into Alaska Miles at a rate of 1:1.3. This means we need to check the Alaska site to see how much the same ticket would cost us. We get some interesting results as you can see from the screenshot below.

Award Ticket Redemption Process- Booking NYC to LAS

The prices are fixed, rather than revenue based, which can lead to interesting results at times. The main cabin fare is more than double the main cabin if you book through Virgin using Virgin miles. But, you can book one way first class on that same flight for only 25k Alaska Miles. Remember I told you Virgin Miles are converted to Alaska at a rate of 1 to 1.3? This means you only need 19,230 Virgin Miles to book a FC ticket. Using the same steps as above, I see that this redemption would give me 3.6 Cents a piece for my Virgin miles. That’s an excellent value and I think it’s an excellent price for First Class.

Estimated Cost of Miles + Cash
  • $390.20 (Excellent considering the cash price for this flight was $699)

We’ll continue on to see what else is available.

JetBlue True Blue Points

Award Ticket Redemption Process- Booking NYC to LAS

Award Ticket Redemption Process- Booking NYC to LAS

You are always free to choose the cheapest rate, but since it’s probably more helpful to compare apples to apples, we’ll stick with the morning flight and base our calculations on the 8:44 AM flight. Going through the same process we did with Virgin, we see that the value of miles for this specific redemption will be

  • 157- 5.60= $151.40/ 10,600 True Blue Points = .0142
    • Our miles will be worth 1.42 cents each
    • TPG values True Blue Points at 1.2 cents each- so we’re okay with this redemption value.

Now we need to look at the price when we upgrade to premium economy. To upgrade, you must purchase an Even More Seat at a cost to you of $70.

Estimated Cost of Miles + Cash
  • 10,600 x 1.2 = $127.20 + 5.60 + 70 = 202.80

Note: If you’re like me and have the JetBlue Plus Card – you get a 10% rebate on the points you redeem for award flights. It would instead cost you 9,540 miles instead and change your valuations to $190.08. This is definitely something to consider if you fly Jetblue routes regularly.

But Wait, There’s More

Another Consideration for me in this scenario is that I have an Amex Platinum Card and my chosen airline for the $200 Annual Airline Fee Credit is Jetblue. This makes things a bit more interesting for me because I can put the Even More Seat on my Amex card and receive a credit for the full $70 (assuming I haven’t used my credit yet). In that case, the estimated value for me, drops to $120 and I’m pretty happy with that number.

Note: I chose Jetblue for my Platinum account, not because it’s my favorite airline (though it may be) but because of the way they charge to upgrade to premium economy. I find that it’s incredibly easy to use the fee credit with them every year because you pay the Even More Space fee separate from your ticket, which means it counts as a fee. Several other airlines do not let you upgrade separately for cash or at all if you booked initially in economy.

Delta Skymiles

From the search pictured below, it’s clear that Delta is not a good option for us. The miles for Delta Comfort are roughly the same number you would need for Virgin First. Although Skymiles are not as valuable, it’s still too many miles considering the other options.

Award Ticket Redemption Process- Booking NYC to LAS

Putting It All Together

I think we found some excellent options and I won’t further complicate our analysis with other options because I do believe we have the best ones covered. The option that is right for you depends on whether you would rather save some miles and stick with the JetBlue Flight for around 10,000 points + $80. Alternatively, would you prefer to splurge for a First Class Ticket for less cash but almost double the miles? I don’t think there’s a wrong answer here!

Both ways gave us good value per mile. If I absolutely had to choose, I would probably select the Jetblue Flight because it’s nearing year end and my platinum card credit needs to be used. I am also always a little nervous about a JetBlue Devaluation because of the way they’ve increased the number of miles they give out in the past 2 years. I also have 300k Trueblue Points. But, there’s no factual basis for that thought, it’s just my own personal worry.


Sometimes, there’s no clear cut best answer. Especially when you’re comparing different fare classes. It ends up being about personal preference. I have flown all three of these options and I would say the First Class on VA was my favorite (no surprise there). But, JetBlue Even More is a great flight as well and I fly it often. As you can see, being flexible and diversifying your options is the absolute best way to save money.




Bethany Walsh
Founder of, Bethany is a points, miles and loyalty program strategist who enjoys luxury travel and lives for a deal. When Bethany is not following her Miles to Memories family around the world to various meet-ups you can find her on a beach, in a casino or on a mileage run.

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  1. My flight decisions have normally been more subjective, so I appreciate the objective way you start with Google Flights, and then use a mathematical comparison. Thanks!

  2. Nice tip on the Virgin to Alaska transfer bump. I would have gone with the FC ticket using Alaska miles 🙂

    Nice work!!

  3. I’d add that there is a good chance that someone with that many B6 points is a Mosaic member. If so, it makes Jetblue an even more attractive choice since an EMS would only cost something like 1,000 points extra.


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