How to piece together an impossible award


Spoiler: In this post I show how it’s sometimes possible to book the most difficult flight awards at low prices by booking two awards instead of one.

Let’s suppose your family of four wants to visit New Zealand during school winter break.  And further suppose you’d like to use your airline miles to fly business or first class.  Good luck with that.  Finding reasonably priced awards to New Zealand (or Australia) in our winter / their summer is hard enough.  Finding those awards during school breaks is impossible.  Or is it?

Default findings = crazy expensive

Your favorite airline will show you award availability for the dates you’d like to travel, but the prices won’t be pretty.  Here are some examples where I searched for flights from Detroit to Auckland, New Zealand, looking for Christmas-break travel for 4 adults:


AA shows awards available for “only” 175K per person one-way in business class:


Delta shows awards available for “only” 465K per person one-way in business class.  While Delta sometimes charges less for round trip travel, that wasn’t the case here.  They wanted twice as much for round trip.


United shows awards available for “only” 200K per person one-way in business class:

The best priced option, above, was 175K AA miles one-way.  That would come to 350K miles per person round-trip.  That’s too much for most of us.

A different route

Finding potential way-points

It may be possible to book two separate awards much less expensively and get to visit another city or two along the way.  To find likely intermediate locations, I recommend Google Flights.  Search for flights between your home airport and your desired destination airport during the time you want to travel in order to find potential routes.  For example, I searched Google Flights for 1-stop options from Detroit to Auckland and found a number of interesting intermediate stops: Houston, San Francisco, Los Angeles, Seoul Incheon, South Korea, and Shanghai, China.

I recommend also checking other easy-to-get-to origin and destination airports to see if there are other routes and intermediary cities worth considering.  By changing up the start and end cities this way, I added the following cities to my list of potential intermediaries: Dallas, Vancouver, Dubai, Hong Kong, Doha, Abu Dhabi.

The intermediary options can be grouped into three buckets: North America, Asia, and the Middle East.  It’s worth checking the way-points in North America by starting your award search from those locations to your desired destination.  You might find that the reason the award pricing was so high in your first search was because it was difficult to get from your home airport to these way-points.  When searching for award flights to New Zealand during winter break, though, you’re unlikely to find much, especially if you’re looking for business class for four.  Asia and the Middle East are better bets.

Where to visit along the way?

If you are open to spending a few days at a way-point, your chance of finding great onward awards to your final destination are much greater because you won’t then have to perfectly match up arrival on one ticket with departure on the other.  Plus, this protects you from the issues that arise if your starting flight is delayed.

For the sake of argument, let’s say that you’d like to visit Asia rather than the Middle East.  The Asian way-point cities we identified above for our trip from Detroit to New Zealand are: Seoul Incheon, Shanghai, and Hong Kong.  But I think it’s worth expanding the search to other Asian cities that we can get to non-stop from our home airport.  To find those options, browse to and enter your home airport. This will show you all of the direct flight from that airport.  For Detroit (DTW), this helps us add the following cities to our potential way-points: Beijing, Tokyo-Narita, and Nagoya. shows all of the direct flights from any airport. Hover over the endpoints to see the airport city and 3-letter code.

Check each permutation to get to the way-point

Our goal now is to find the best award flight to Asia, then the best onward award fight from Asia to New Zealand.  In the example given here, I searched for awards from Detroit to Seoul Incheon, Shanghai, Hong Kong, Beijing, and Tokyo.  I also ran a few searches from some easy-to-get-to airports such as Chicago and Washington DC.

I used the Juicy Miles tool for my searches, but it’s possible to find most of the same results by searching a number of airline websites: AA, Delta, United, Alaska, BA, Virgin Atlantic, Air France, …  You can also use a tool like Expert Flyer, but you’ll then have to check for the awards one carrier at a time.

Regardless of how you search for awards, I highly recommend creating a spreadsheet to record all positive results.  You’ll want to store the from/to and stopover airports involved, the airline carriers, the start and end dates and times, the best points price you found, etc.

Yes, this is a lot of work, but if you want to book an impossible award, this is a way to do it.

Rather than painstakingly take you through my results for this example impossible trip, here are the best options I found for the outbound portion of the trip:

DC to Hong Kong on Cathay Pacific for 50K or 70K

Juicy Miles shows that AA charges only 70K per person one-way and Alaska charges only 50K per person one-way for this crazy long flight to Hong Kong on Cathay Pacific’s A350.  Juicy Miles doesn’t currently sort the results on the left by the lowest award prices, so I had to scroll way down to the bottom to find the Alaska Airlines pricing.  In this image, I filtered out all other options to make the best options clear:

Neither nor show this award, but I was able to confirm it’s existence via both the website and

If I were to use this option, I’d position to DC (via Delta) in the late evening on December 27th.

DTW to Beijing, Tokyo, or Seoul

Virgin Atlantic is the best program for booking international non-stop Delta flights.  Virgin Atlantic’s website shows that 60K awards on Delta One Suites are widely available to both Beijing and Tokyo for four adults in Delta One Suites.  Here’s the availability to Beijing, for example:

Virgin Atlantic’s website doesn’t know that the Seoul Incheon airport exists, so I checked Juicy Miles for availability instead.  I could have also used Air France to check for availability.  Anyway, award flights to Seoul Incheon are widely available as well.

Check each permutation to get from your way-point to your final destination

One of the best options I found was via the website.  For some reason Juicy Miles didn’t show this option except when I searched specifically for PEK-SYD.  Via AA, Qantas business class is available for four people from Beijing to Sydney and then onward on the short flight from Sydney to Auckland in economy.  All for 40K AA miles.

Put it all together

Delta One Suites

For my outbound journey, I would book Delta One Suites from my home airport Detroit (DTW) to Beijing (PEK) for 60K Virgin Atlantic miles per person.  We would then make sure to stay in Beijing for less than 144 hours in order to take advantage of China’s visa-free transit policy which is normally 72 hours, but has been extended to 144 hours in select cities including Beijing.

The Great Wall

After a few days checking out Beijing’s sites (or, just one action packed day), we would continue on in Qantas business class to Sydney and then Qantas economy to Auckland for 40K AA miles per person.

Total one-way cost

  • Detroit to Beijing: 60K Virgin Atlantic miles per person
  • Beijing to Auckland: 40K AA miles per person
  • Total: 100K miles per person

Repeat for return journey

Yes, again, this is a ton of work.  But keep in mind that our goal is seemingly impossible: business class for four to New Zealand during school winter break for a reasonable number of miles.

In this example, finding good return flights to the US is even harder than finding good outbound flights.  When searching for just two people, I found Qantas first class available to Hong Kong for only 50K AA miles per person.  That would be awesome.  But, the best 4-person options I could find were Fiji Airways to Tokyo for 40K AA miles per person, or Korean Air for 62.5K Korean miles per person (or 113K Air France miles per person).

Other options include splitting up: send two people first class on Qantas, and two people in economy, for example.  Another option is to expand the way-point searches to include other Asian cities, or to other continents.  Or, find the best business class option from Asia to home and book economy to Asia from New Zealand for only 30K AA miles per person.

It’s very important to note too that award space comes and goes over time.  While it’s rare for much new award space to appear for high-season flights, it could happen.  This is where Expert Flyer comes in extremely handy.  Expert flyer lets you set email alerts for flights you are interested in, and you’ll get an alert when the awards show up.  Unfortunately, like Juicy Miles, Expert Flyer is not free.


Airline miles are usually the best currency around for booking international business or first class flights.  If you travel as a family, though, and your travel dates are restricted by school breaks, it can be really difficult to get the flights you want for reasonable numbers of miles.  This is especially true if your goal is to fly from North America to Australia or New Zealand in our winter / their summer.

In this post I showed an example of how it’s possible to piece together a four-person business class award to New Zealand for a reasonable number of miles during high season.  The trick is to find a way point that is in less demand and where you’d happily spend a night or two on your way.  It’s not easy to piece this together, but it can be well worth the effort for some.

Good luck and happy hunting!

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