The Cranky Flier’s travel route, re-posted from his website so you can see how bonkers this all is.

This is complete madness, but the guy as one good reason for doing it. Well, he has one good reason and a generous background of general lunacy.


The flier in question is a dude who goes by the handle The Cranky Flier. He’s an air travel blogger and to celebrate his tenth anniversary of blogging air travel-related blogs, he came up with a brilliant plan to get himself an incredible deal for a free flight pass. All he had to do was reach nine airports from a total of eight flights, all in one day, and all in the great state of California.

Here’s how it all works, as the Cranky Flier himself explains:


Southwest put a targeted offer out to some Californians so it could try to boost spending. The idea is simple. Fly 10 one way flights before October 31 and you get a companion pass from then through the end of 2017. For those who aren’t familiar, the Southwest companion pass is a magical thing. Anytime I fly, I can have my companion fly with me for free (well, plus a few bucks in taxes).

I already had a roundtrip from Long Beach to Oakland last weekend (trip report coming), so that leaves only 8 flights to go. I thought about just running back and forth on $39 fares between Oakland and Long Beach a few times, but that wasn’t really going to be all that exciting. Instead, my crack team at Cranky Concierge got to work.

He’s scheduled to fly from Long Beach to Oakland, from Oakland to Ontario, from Ontario to Sacramento, from Sacramento down to Orange County, from Orange County to San Jose, from San Jose to Burbank, from Burbank to SF, and finally from SF to LA. He has one 25-minute layover in Burbank and two 20-minute layovers in Sacramento and SF. This could be tough.

And he’s currently in the midst of this whole operation as we speak! He has a guide on how to follow along with his travels on his blog here and on Twitter here. Pray along with me that he doesn’t get sat next to a screaming baby.


(Hat tip to the wonderful Tamerlane’s Thoughts!)