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How I Book Award Flights Using Points and Miles

Because I travel full-time, I am very flexible with my dates and the cities I fly from or to. I do not always need to fly on a specific day, so I am able to play around with the dates and routes until I find a good deal.

One tool I use almost every time is PointsYeah. It shows me which airline has award space and which points program I can use to book the flight. I like it because the layout is simple, and the free version is more than enough for me. You do need to create a free account to use it, but there is no need to upgrade to a paid version.

  • The left side of the search results shows the flight information

  • The right side of the search results shows the points programs and any transfer bonuses

To make things clear, I will walk through an example and explain what each side means.


Example: Hanoi, Vietnam to Tokyo, Japan

Let’s say I want to fly from Hanoi (HAN) to Tokyo Haneda (HND).
This is just an example route, but the same idea works for any city.


How I Start My Search

When I search for flights, I keep things very simple.

I start by selecting one-way, even if I plan to come back later. Searching one-way gives the tool more flexibility to show the best deals.

Next, instead of choosing one fixed date, I select a four-day window.
For example: April 24 to April 27

This helps because the cheapest award price is not always on the exact day I first imagine. Sometimes switching the flight by one day can save thousands of points. By giving PointsYeah a small date range, it checks all the days for me and highlights the lowest option.


Full View: What a Search Result Looks Like

Below is a full PointsYeah-style view. The left side shows the airline and flight details, and the right side shows the points programs and any bonus offers.

PointsYeah search results example – full view showing an award search from Hanoi to Tokyo

(This example displays a Vietnam Airlines flight from Hanoi to Haneda.)


The Left Side: Airline & Flight Details

The left side of the search results tells me everything I need to know about the flight itself. It usually shows:

  • Airline name
  • Flight number
  • Departure and arrival times
  • Flight duration
  • Whether the flight is nonstop
  • How many award seats are left

Award seat availability is very important. If PointsYeah shows that only 1 seat is left for that award price, there is a risk that someone else books it before I finish my own booking process.

If the award seat disappears after I transfer my points, the points cannot be reversed, so they will be stuck in that airline program. This is why I pay close attention to the number of seats.

Here is a close-up view of the left side of the search results for this route Hanoi (HAN) to Tokyo Haneda (HND):

Close-up of the left column in PointsYeah showing airline and flight details


The Right Side: Points Programs & Transfer Bonuses

The right side of the search results is where I save the most points.

Here, PointsYeah shows:

  • Which transferable points programs can book this award
  • How many points are required
  • Any transfer bonuses that reduce the number of points I need
  • Which airline loyalty program handles the booking

For example, if American Express Membership Rewards has a 40% transfer bonus, I might need fewer points than using Chase or Citi. In this example, you can see that Amex had a transfer bonus to Virgin Atlantic at the time of my search, which dropped the required points from 15,500 down to 12,000. This is why I always check this section carefully before transferring any points.

Here is a close-up of the right side of the search results:

Close-up of the right column in PointsYeah showing points transfer options and bonuses


What I Do Before Transferring My Points

If I like the route and the deal, I do not transfer points right away.

Instead, I go directly to the airline’s loyalty program website to verify that the award flight is still available. This is called confirming the live award inventory or award space.

I only transfer my points after I see the same award flight available on the airline’s website.

Once points are transferred, they usually cannot be reversed, so I only transfer them when I am 100% sure the award seat is still there.

This is especially important when PointsYeah shows only 1 seat left, because someone else may book it before I complete the transfer. If that happens, the flight will disappear and I would be stuck with the points already moved into that airline program.

So the sequence I follow is always:

  1. Find the deal on PointsYeah
  2. Check the same award flight directly on the airline’s website
  3. Confirm the award space is available
  4. Transfer the points
  5. Immediately book the award flight

This avoids losing points or missing the seat.


How I Decide If It Is a Good Deal (Cash vs Points)

When I want to know if using points is a good deal, I look at one thing:

How much money do I save after adding the taxes?

Award flights always have taxes, and sometimes the taxes are high.
So I compare:

  • The cash price, and

  • The points price + the tax I must pay

Then I check if the value is around 1.5 cents per point or 2.0 cents per point, which is what many smart people in the points-and-miles world use.

Here is the simplest way to understand it:


🟢 GOOD DEAL = About 1.5 cents per point or higher

🟣 GREAT DEAL = About 2.0 cents per point or higher

Now here are clear examples, with taxes included:


🟢 Example of a GOOD deal (1.5 cents per point)

Cash price: $300
Award price: 20,000 points + $40 tax

You pay $40 instead of $300 , so you save $260 using 20,000 points.

  • $260 saved ÷ 20,000 points = 1.3 cents per point (almost good)

  • If the savings were a bit higher, it would hit 1.5 cents, which is considered a good deal


🟣 Example of a GREAT deal (2.0 cents per point)

Cash price: $500
Award price: 25,000 points + $50 tax

You pay $50 instead of $500, so you save $450 using 25,000 points.

  • $450 saved ÷ 25,000 points = 1.8 cents per point (close to great)

  • If the savings hit around 2.0 cents, it would be considered a great deal

This is the kind of redemption people love.


🔴 Example of a BAD deal (low value)

Cash price: $120
Award price: 20,000 points + $60 tax

You pay $60 instead of $120, so you save only $60 using 20,000 points.

  • $60 saved ÷ 20,000 points = 0.3 cents per point (very bad)

Here, paying cash is much smarter.


The simplest rule possible

  • If using points saves a lot of money, it’s a good deal (about 1.5 cents or more).

  • If it saves a huge amount of money, it’s a great deal (about 2.0 cents or more).

  • If it saves only a little money, it’s not worth using points.


Real Example From My Search

In the screenshot above, the award price was 12,000 points + $76 tax, and the cash price for the same flight was $430.

Here is how I check if this is a good deal:

  1. Cash price: $430

  2. Award price: 12,000 points + $76 tax

  3. Money saved by using points: $430 – $76 = $354 saved

Now divide the money saved by the number of points used:

$354 saved ÷ 12,000 points = about 2.95 cents per point

Most people in the points world consider:

  • About 1.5 cents per point good

  • About 2.0 cents per point great

This example is close to 3.0 cents per point, which makes it an excellent deal.

This is the kind of award value I look for, because the cash price is high and the points price is low.

Why This Works So Well for Full-Time Travel

Since I travel full-time, I do not always have a strict schedule. I can move my dates around, check nearby airports, or even try different countries. PointsYeah makes this very easy because I can see the cheapest option in seconds.

I keep adjusting the dates and the route until I find a price I like.
Sometimes the cheapest option is leaving a day earlier.

Sometimes it is flying from a different city.
This flexibility saves me a lot of money and points throughout the year.

Using one-way searches, giving yourself a small date range, checking both sides of the PointsYeah screen, verifying award space before transferring points, and comparing cash vs points are very simple habits that help me find cheap award flights almost every time.

If you are flexible with your travel like I am, this tool makes award booking a lot easier and a lot cheaper.