I’m about as close to an Orbitz fanboy as you can find on the internet. I even signed up for the Orbitz rewards credit card, and I continue to book with them even after they eviscerated their best price guarantee program. That’s why I was supremely annoyed to find this in my inbox as I was sitting down to enjoy a burger at my friend Grant’s ‘meat’-up this afternoon:

Cancellation email from Orbitz. Whoever sent that must have known I'm Japanese, since my name is backwards.

Cancellation email from Orbitz. Whoever sent that must have known I’m Japanese, since my name is backwards.

For context, AA has been running some $100.60 round trip fares to Dallas from San Francisco. After all the rewards I can get, it ends up costing me about $93 for each round trip, so I decided to book two back-to-back for next week to start padding my Alaska mileage account and re-qualify for elite status for 2017.

Wait. Did I just say I’m taking a mileage run?

Yes, I did. I’ll give you the math really quickly and get on with my story, but after all is said and done, each round trip earns me redeemable miles at about 1.6 cents per mile and elite qualifying miles at 3.2 cents per mile. I’ll happily buy Alaska miles at that price, and I thought the experience itself would be fun (i.e. worth my time) since I can work from the plane as long as I have internet.

Anyway, on with my story.


Needless to say I was livid and not looking forward to doing battle on the phone (and sitting on hold for an hour), especially because I think it’s impossible to actually get what you want if you’re dispassionate (so I’d have to ‘work myself up’). I considered having GoButler do it (and they were more than willing), but this needed a special touch.

After speaking to the front-line rep, who countered that they had notified me by phone (3 minutes before the cancellation email, having left no voicemail; I sure as hell wasn’t picking up a call from a random number in Chicago) before canceling and that the best he could do was book at the new, higher price of $150.60 and then offer me a ‘voucher’ for $50.

“That’s unacceptable.”

“Okay. I’ll get a supervisor.”

And then the wait. 30 minutes. 40 minutes. At minute 51 of my phone call, I finally got to speak to a supervisor, who said she needed to speak to the ticketing department to investigate why the ticket had gotten cancelled.

While she waited, I stated my case. I didn’t pull a DYKWIA to the letter, but stated that I was a loyal customer who spends thousands of dollars a year at Orbitz (which is true; I spent thousands of dollars LAST year, almost all of which were earned from best price guarantee claims 😉 ) and hoped she understood my frustration since the flights were so clearly distinct. Then I told her that the only outcome I’d accept was having my original ticket reinstated and receiving another 100 Orbucks on top as a courtesy.

“I’m sorry, but I need to speak to the ticketing department.”

To be clear, I knew both of these conditions were ridiculous (the first impossible; they can’t ‘reinstate’ a ticket), but I did it to anchor her and make myself appear reasonable with my next proposal: that they ticket the flight at the new price, issue a refund for the difference, and give me 50 Orbucks for my trouble.

That worked. And I suspect it did for two reasons. First, the anchoring. I asked for something I knew was impossible and as a result, appeared to be making a concession when I asked for what I really wanted. Second was more subtle but hopefully a good takeaway if you ever find yourself in a similar situation: the mechanism I specified is a process that I know they have because it’s exactly how their best rate guarantee works. I didn’t specifically say that, but getting her thinking along those lines definitely got the ball rolling.

Thankfully, this turned out well enough (and since this was a mileage run anyway the downside of not taking the flight was very low), but it was an extraordinarily unpleasant experience. Any other Orbitz horror stories out there? What about other OTAs?