Kayak: A Step Behind SideStep

This online dynamo scans hundreds of travel sites for the best deals. Yes, it's good, but it can't match its closest competitor

Editor's Rating:

The Good: Aggregates listings from hundreds of sites

The Bad: Not always the best deals. Lacks SideStep's price-comparison toolbar

The Bottom Line: A leap ahead of traditional travel sites, and could catch up with SideStep

I generally find toggling between various Web sites for the cheapest airfares or hotels a time-consuming annoyance, however necessary it may be. So when my editor asked me to do a series of travel Web site reviews, I figured, well at least I'd be working as I planned coming trips to Cincinnati, Memphis, and Hawaii.

Don't get me wrong -- even my least-favorite sites have come a long way in recent years, with features like handy calendars that pop up when you want to pick a date, and automatic searches of nearby airports. But in this age of advanced Web services, it seems an anachronism to have to go to a site, enter information, wait for results, comb through them -- and then do it all again on another site. There's got to be a better way.

Turns out, there is. There's a budding crop of so-called meta-search providers that scour loads of other sites for the best deals. They offer a wider selection, including airlines such as JetBlue (JBLU), and are faster and easier to use than more established online agents like Expedia (EXPE) and Travelocity. And they boast navigation tools that let you slice and dice searches nearly any way you want.


The first one on the market, SideStep, was the subject of last week's review (see BW Online, 5/13/06, "Don't SideStep This Site"). This week I am looking at a fast-charging competitor, Kayak.

This is no fly-by-night operation. Kayak was started in January, 2004, by several of the original founders of Orbitz, Travelocity, and Expedia, and it has raised $30 million to date. On May 22, it's set to announce yet another round of funding. Kayak is using the money to develop features, such as social networking applications that could help you better plan trips with friends and share vacation photos. And in good old 1999 dot-com style, it's also launching a marketing blitz.

Like SideStep, Kayak does an outstanding job of ordering up scads of low airfares in seconds. It took less than a minute to come up with more than 800 early June flights from San Francisco to New York, from rivals like Cheaptickets.com to the airlines themselves (who knew Alaska Air (ALK) traveled that route?). They're served up starting with the cheapest ($295) to the most expensive ($970), but you can rearrange results just about any way, narrowing the price range, eliminating certain airlines, reducing the number of stops – you name it. Kayak does that by using a programming technology known as Ajax, which is designed to make a faster, more interactive Web site.

But as good as Kayak is, I found it didn't consistently dig out the cheapest fares. And Kayak lacks the toolbar I found so helpful on SideStep. Once downloaded, it automatically pops up and starts scouring its own inventory every time you log a search on a competing travel site -- no reentering data, no flipping between windows or taking notes. Kayak Chief Executive Steve Hafner sniffs that SideStep's tool is little more than glorified spyware. You know what? I don't care. It lessens my travel-planning headaches and I love it.


None of this is a big knock against Kayak. Both it and SideStep have taken online travel searching to a new, much more pleasant level. And there are a few reasons to go pick Kayak over SideStep. It has multicity search, which SideStep lacks, and is about to introduce flexible travel dates, letting you search for travel within a preset number of days before or after a given date, another feature I love. Typically, I don't have to travel on exact dates, and I'd like to know the best fare without having to do multiple searches.

SideStep should take note. These are still early days in the meta-search wars and Kayak could yet outpace its competitor with better features. But until then, it's more of an occasional tool than regular online destination for me.

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