That sinking feeling has produced what might be called the second generation of Web travel sites that try to remedy it. The poster child for "travel Web 2.0" is Kayak.com. With an executive roster that includes former top management at Expedia, Orbitz, and Travelocity (the giants of "travel Web 1.0"), Kayak's founders like to call themselves the "dream team" of Internet travel. We prefer to leave the dream teams to basketball and comic-book heroes, but that pedigree has generated buzz since before the site launched earlier this year. Does it live up to the hype?
Kayak (like its competitors SideStep.com and Mobissimo.com) tries to allay your worry by searching dozens of travel sites at once. It doesn't charge you anything; it simply points you to providers — airlines, travel agencies, hotels — that will book your reservation. The interface is simple, providing a wealth of information without burying you in data, and sorting options that let you home right in on what you want. We particularly liked the ease with which Kayak lets you filter out flights from congested metro airports and list only ones at nearby business-friendly airfields. Hotel choices are linked to commentary from across the Web to let you vet options quickly.
But even a dream team needs to eat, and there's the rub. Kayak charges the site on which you book your travel, and not everyone wants to pay for the lead. So Kayak doesn't search every travel site out there — and can miss deals. Kayak doesn't search Hilton directly, for example, and it returned rates higher than those we found there. It doesn't search overseas airlines directly, either; SideStep does a better job there. Kayak is worth adding to your online travel arsenal, but if you're looking for that one site...well, keep dreaming.
A version of this article appeared in the August 2005 issue of Fast Company magazine.