Expedia Thinks It Can Help You Find the Vacation You Didn’t Know You Wanted

Expedia has bet everything on understanding the psyche of the modern traveler.

- Drake Bennett, photo by Tina Schula

On a Monday morning in mid-October, in a suburb of Seattle, a young woman named Megan went online to make some travel plans. She and her parents, along with her siblings and their spouses, wanted to go somewhere tropical in January, and in a flurry of texts and Facebook messages, Belize had emerged as the leading candidate. It had fallen to Megan, as it often did, to execute. So, a little after 9 a.m., she typed the name of the online travel agency Expedia into her browser bar and began to explore flights.

Her preference was for Alaska Airlines—she’d had good luck with the carrier—but when she couldn’t find anything, she started looking at American. She noticed there was only one ticket left for the least expensive flight, which caused her some concern. She grew more apprehensive as she noticed that the cheaper available flights had long layovers. Then she saw that some of the layovers were in Los Angeles, and she briefly considered a visit to Disneyland.

After eight minutes, without settling on a flight, Megan began to explore hotels. The photos from a “jungle spa” resort caught her eye—it looked adventurous but also pampering— so she was crestfallen when she noticed that it was booked up for the dates she wanted. “Oh, so sad,” she said softly. She looked through the reviews of another promising hotel and found it had no Wi-Fi, which wouldn’t be a problem, but also ants, which would. She stumbled onto a review someone had written about going to a resort to recover after “a surprising end to a marriage engagement.” That bummed Megan out a bit.