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This is a guest post from Chase Tajima. Chase is a tax attorney in Honolulu–Aloha! He writes about Hawaii tax law at Anyone is welcome to submit a guest Anatomy of an Award post, so we can all learn from interesting award bookings.

I started following MileValue because I wanted to find a cost effective way to get from Honolulu to Delhi, India to attend my college roommate’s wedding. Roundtrip flights from from Honolulu to Delhi ranged from about $1,600 to $2,000+ in economy. I found to be the only blog that effectively taught award booking rules step-by-step. [Scott: Thanks, Chase!]

I started by learning about The Five Cardinal Rules of American Airlines Awards. While most of the rules were fairly easy to follow, the fifth rule–unique to American Airlines awards–is incredibly frustrating:

Awards between Region A and Region B cannot transit Region C unless specifically allowed.

What this means is that an award from Honolulu (North America) to Delhi (Middle East/Indian Subcontinent) cannot route through another region, say Asia 1 (Tokyo).

There are exceptions to this rule. One of these exceptions is that a routing may traverse Europe to get from North America to the Indian Subcontinent. In other words, to get to India, one must either fly directly or one may route through Europe. All other routings are invalid.

Under this exception, I could have routed through Europe, but I wanted a free oneway prior to my flight to India. This meant Honolulu would have to be my international gateway city because stopovers are only allowed at the North American international gateway city on AA awards and you have to stopover at your home airport to employ a free oneway. This, in turn, meant that I had to try to fly west over the Pacific through Asia to get to India.

How could I get a free oneway and follow AA routing rules?

I called the AAdvantage desk at 800-882-8880 to reserve an award flight from Los Angeles to Honolulu–my free oneway–with a month long stopover and then Honolulu to Delhi. The first agent said it wouldn’t be possible to have a stopover in Honolulu because it couldn’t be my international gateway city traveling to India.

With AAdvantage miles in short supply, I hung up and decided to get creative.

I took a look at the AA award chart, which specifically requires that a North America to India award be transatlantic only. That award is 45k miles each way in economy class.

But what if I went through Asia?

Going from North America to India via Asia would mean that my award would actually be two awards from AA’s perspective. USA to Asia and Asia to India.

I found space for flights from Honolulu to Tokyo and Tokyo to Delhi. Could I make it work?

The wedding is scheduled for November, which is a break for me. That means that my USA to Asia 1 flight falls during the off peak dates of October 1 – April 30. That means that Los Angeles to Honolulu//Honolulu to Tokyo priced at 25k miles oneway.

Tokyo to Delhi is 22.5k miles each way year round. My total trip priced at 47.5k (25k + 22.5k) miles. That’s 2,500 miles more than if I had routed through Europe, but look at the benefits:

1) Free oneway from Los Angeles to Honolulu. If I’d routed east through Europe, there would have been no free oneway possible. I value the free oneway at $200.

2) Free stopover possible in Japan. Normally free stopovers are only allowed on AA awards in North America. But because AA saw my award as two awards, I could stop in Japan for as long as I liked. [Scott: This is the way to get free stopovers abroad on AA awards; break one award into two. Sometimes this can even save miles, like if you broke New York to Amman into New York to Berlin and Berlin to Amman during the winter. The award would drop from 45k to 40k (20k + 20k) AA miles.]

3) More direct routing from Honolulu. Heading west saved me about 5,000 miles of flying, which is about ten hours I don’t have to be in an economy class seat!

4) Routing west meant no chance of flying British Airways, which would have cost hundreds of extra dollars in surcharges!

5) I was able to upgrade to business class for part of the award at a low miles price. If I had flown east and wanted one segment in business class, the whole award would have priced in business class–67.5k miles. But since flying west meant two awards, when I later decided to upgrade Tokyo to Delhi, it only cost me 7,500 extra miles to change from JAL economy to Cathay Pacific business class. Now the award is half economy–to Tokyo–and half business–to Delhi–for 55k total.

Is this useful for non-Hawaiians?

People on the west coast may find shorter routings heading west to India than east. To unlock those shorter routings, they can head west breaking their one award into two. It will cost a few more miles, but they will have the benefits I mentioned above. And they can stopover for free in Asia, which they would normally not be allowed to do.

What about people who want to fly business class?

There is a bigger premium to fly business class west to India. Flying east would cost 67.5k miles each way in business class. Flying west would mean two awards: 50k to Asia 1 and 30k more from Asia 1 to India for a total of 80k each way. That 12.5k difference is bigger, but may be worth it for people who want a better route, a chance to fly Cathay Pacific, or a free stopover in Japan, Korea, or Mongolia (Asia 1).


The award chart and AA agents will tell you that you can’t route west from the US to India. But you can, and I’ve ticketed exactly that. The trick is to ticket the trip as two awards–one from the US to Asia and one from Asia to India. During the winter in economy class, this is only a 2,500 mile premium over heading east.

During the summer and in business class, the premium is larger. But heading west has great benefits–the biggest of which may be unlocking a free stopover in Japan, which is otherwise impossible on an AA award.

And it wouldn’t be an AA award without a free oneway. Make sure you are grabbing all the free oneways, stopovers, and open jaws you are entitled to.

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