Jim Stewart’s trip was a disaster before he even left for the airport. When he tried to reserve a package vacation through Expedia, the price mysteriously went up. He made another reservation, tried to cancel it, rebooked another one and — you guessed it — ended up with two reservations for the same trip.

He explains,

I booked a flight, hotel and auto with Expedia for $872. Three days later they informed me the “new” price was $1,091. I called them and told them to cancel everything.

I then booked flights, etc., on my own for the exact dates that Expedia had originally booked. They went ahead and billed us for the $872 [for the first trip]. When we called them, they said I did not cancel the original flight.

I’ve talked to at least four different people who seemed trained in talking in circles. I finally wrote the general counsel on Aug. 3 and again on Aug. 17, but haven’t heard anything.

There’s so much to learn from this case, it’s hard to know where to begin.

But before we do, here are the results of a quick poll I ran between 8:30 and 10:30 a.m. this morning. There were more than 500 responses.

What went wrong here? We’ll get to what happened over at Expedia in a moment. But let’s start with Stewart. It looks as if he spent some quality time on the phone. Unless he recorded the call, he’d have no verification that he tried to cancel his vacation. I would have tried to at least get some kind of verification in writing. Appealing to Expedia’s attorney is fine, as long as you go through channels first. It looks as if Stewart didn’t.

I checked with Expedia. Here’s what it said in a response to Stewart:

Through reviewing your letter, we see that you purchased a vacation package and then received an email that the package was not booked and the price had increased.

We have reviewed the enclosed documents you have provided and found that you saved an itinerary online under the account of Jas Stewart on May 23, 2010. We then show that you called into our Sales Department and purchased an identical flight and hotel package under the account name of Betsy Stewart along with a car reservation on [your] itinerary.

The enclosed documents provided show that you received an email for the saved itinerary due to a price increase. With saved itineraries, our system will generate a standard email should the price increase to advise our customers should they still pursue to purchase the saved itinerary; however, you were already confirmed on the flights and hotel reservation purchased via [your second itinerary].

You stated in your letter that you contacted our Customer Service Department to cancel the reservation on May 26, 2010 due to the fare increase. We have no record of a cancellation being requested or processed on that date.

In other words, so sorry. The flights were non-changeable, non-cancelable, the rooms had a no-show penalty. Stewart is basically out of luck. However,

As a gesture of goodwill, we have applied a $50 Expedia Travel Coupon into your Expedia.com account under Betsy Stewart. This coupon is valid for one year and can be used towards a future Expedia Special Rate Hotel or Vacation Package purchase.

So if I’m understanding this correctly, it appears his first itinerary was saved but not confirmed. He then booked another itinerary through Expedia under a different name, and tried to cancel it, but didn’t.

If you’re confused about how all this works, and indeed, if this entire case confuses you (as it does me) then you can read up on how reservations are saved and booked through Expedia’s system here. Bottom line: Steward would have been better off canceling his request online.

There’s something funny about this case. Seems to me Expedia should either sell a vacation on its site, or not. “Saving” an itinerary that could go up in price and then somehow gets booked, is troubling to me.

If nothing else, perhaps its time for that proposed law that would allow us to access our call-center conversations?

Update (noon): When my Expedia contact called this case “confusing” he wasn’t kidding! I’ve reworked this post a few times, thanks to reader comments and re-reading all of the correspondence. Wow. What a mess!

(Photo: Jonathan C aves/Flickr Creative Commons)