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Exploring award options is something I love doing, and I have been on quite the binge lately. I thought I’d share a number of the craziest routing options I’ve found.

Chicago to Tokyo via…Africa?

Yes, it’s true. This is a completely valid award. I stumbled upon it when searching for ANA first class space between Chicago and Tokyo.

Normally, I wouldn’t have given it a second look, as Ethiopian had been popping up in options due to their fifth freedom flight (SEE: What is a fifth freedom flight?) between Tokyo and Seoul. But when I saw *only* Ethiopian listed as the operating carrier, I thought it must be a fluke. Nope. You can fly 14,000 miles to get to Tokyo this way.

Given that there are awards available directly between the Windy City and Tokyo, it makes pretty much no sense to fly literally twice as far, unless you’re a crazy avgeek. I have to admit, flying via Addis Ababa to Tokyo from Chicago does sound like a whole lot of fun. And a whole lot of time on a 787. I might regret the idea.

The one thing that sticks in my mind about airline routing options is the old “most powerful zone” United award concept, discussed at length by Travel is Free in this post (it is ancient history, published in 2013). It is supposed to be dead. But I really don’t know why else you’d be routed this far to get to Tokyo for the same price. Japan was a more powerful zone than Africa, which could have been used to great advantage under the old stopover rules (may they ever rest in peace).

Transcon flight *east*, then off to China

Alaska admittedly has a number of odd routings to offer. But one of my favorites is the transcontinental flight from SFO to New York, followed by a Hainan flight to Chengdu. You’re going pretty much the opposite direction for the first five hours. But hey, if you love being on planes, why not?

You can actually exploit this to great advantage if you live in New York. Simply break up your award in NYC as a “stopover”, and voila, half of your ticket is the return from one trip, and the other half is the beginning of another. Totally legal, and an amazing use of the stopover perk on one-way Alaska awards.

First time I tried it, though, I got something even more ridiculous. Alaska is cray cray.

South Africa to South America via Paris

There aren’t a whole lot of options between South America and South Africa, but given that anything else is pretty circuitous, both LAN and South African Airways do fly a few routes. Both serve the São Paulo to Johannesburg route.

Revenue flights might not always give you the same crazy options, but the award computer seems to think flying to Rio via Paris is A-OK. There isn’t much in terms of SkyTeam options between these two continents, so it may be all you have available.

Turning an 8-hour into a 12-hour flight plus two connections

Singapore Airlines flies Melbourne, Australia to Singapore nonstop. A lot. There are like five flights a day. Scoot, Qantas and Emirates also operate between the two cities. But what if you want to take the scenic route?

If you’re feeling adventurous, you can trade the 8-hour nonstop for a 12-hour flight. First, fly to Auckland. Then take off for Bangkok. Then finish the trip to Singapore. Hey…if you’re flying business class (especially if it is Thai’s new 787 layout), what’s the loss? Besides time, of course.

I tried to get a ticket to price out from Perth to Singapore via Auckland. No dice. That would be even better.

America to America via…Europe?

The best way to fly to Brazil from New York is nonstop on any of the four carriers that serve the New York to Rio route. But what about flying Air France the whole way? Sure! Let’s do it.

I mean, if you like airplanes, why not? The mileage cost even even all that bad. Air France A380 economy is pretty nice as well (SEE: Air France A380 Economy Review: Paris to San Francisco). Maybe if you can find an itinerary with a 23-hour layover in Paris, you can actually buy yourself a fun day in Europe for no extra charge!

Conclusion

So maybe I’m crazy for thinking a couple of these are even half-tempting. But I thought these were all great finds, at least for entertainment purposes. I don’t know, though. Maybe you’ll find I flew via Addis Ababa on my first trip to Tokyo.

Maps generated by the Great Circle Mapper – copyright © Karl L. Swartz.

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