The Daily Parker

Last night I poked around aa.com, musing about taking a pair of trips this fall. Two, because during the fall and early winter, airfares and hotels are cheaper than the rest of the year, at least in the places I like to go.

My original thought was to buy a trip to London and use miles for a second trip somewhere else, on the theory that with 8 daily non-stops between Chicago and London, fares would be lower than to somewhere that has only one daily flight. No, not so much.

For travel the weekend of 10-15 October, here are the best airfares I found on oneworld carriers:

All of the options save London have one daily non-stop from Chicago. As you can see, they're in order by distance, and also as you can see, there seems to be no connection between the distance (a proxy for the cost to the airline) and the airfare.

To add more confusion, all of those destinations cost 30,000 frequent-flyer miles (except for Honolulu, at 22,500, and Hong Kong, at 35,000) each way in coach or 50,000 each way in business. I say "confusion" because now I'm trying to balance two competing miles forces and coming up with a deranged result.

The pressures are these: earn the most flight miles per dollar—flight miles are super valuable compared with other kinds—and spend the fewest flight miles per trip. As you can see from the data, it actually works out better if I use miles on the shorter trip (to London or Berlin) and buy my ticket for the longer trip (to Asia).

Just a little more figuring, including the cost of upgrading to business class on overnight segments and each city's hotel costs, and holding the dates constant, puts 10 possible trips in this order:

Quito, Ecuador; Honolulu; Hong Kong; Dublin; London; Madrid; Manchester, U.K.; Dusseldorf; Tokyo; Berlin; Paris; Santiago, Chile

How did that happen?

Quito is cheapest because without overnight flights, I won't upgrade from coach. And their hotels are really cheap.

Santiago comes out most expensive because both directions have overnight flights.

Hong Kong comes in so inexpensive because I can't use miles to upgrade on any airline other than American, British Airways, or Iberia. The Chicago-Hong Kong flight is Cathay Pacific. I will fly that route someday—but not all the way in coach. Fourteen hours on a plane is fine; but not overnight in coach.

Dublin looks like a back door into London, since flights from Dublin to London are around $150 round-trip; but London works out to be cheaper because AA runs a morning flight from Chicago. No upgrade needed.

I have to conclude the following: because of the insane airfares to Europe and the equally insane airfares to Tokyo, caused by the weak yen and European departure taxes, the cost-per-mile to Tokyo is about half the cost-per-mile to London. Ergo, buy the Tokyo ticket and get the London one for free.

Will I actually take these trips? I can't say. I hope so though.