Priceline Founder Unveils New Flexible Booking Website

Upside.com, Jay Walker's latest innovation in travel marketing, is now live in beta. Although it's aimed mainly at business travelers who aren't fully managed, a representative suggested that leisure travelers might find it useful, as well. Jay Walker founded Priceline, so anything he does deserves your attention. Whether it deserves your patronage is a bit less certain, but it might well be.

The basic idea is simple: Flexibility can cut your costs. Once you decide on a specific itinerary, Upside.com can show you how being a bit flexible can lower your cost.

Here's how it works. To arrange a trip, you start by entering your departure and arrival cities, dates, and other requirements, including ticket refundability and hotel star rating. Then, Upside.com's "Flexibility Engine" software analyzes and scores more than 20,000 round-trip flight and hotel combinations that could work for your trip. It returns and displays six customized choices of "business quality" flights and six choices of hotel rooms that meet your needs. You choose preferred flights and hotel, separately.

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The system then calculates and displays your selected flights and hotel room bundled together for one price, which Upside.com says is "money saving." If you take this option, you or your company pays less than you otherwise might, and you get a gift card. But Upside.com also displays alternative bundles that cost even less than your preferred choices. If you have enough flexibility to take one of the suggested bundles, your company still pays less than it would have and you get a higher-value gift card for yourself.

As of today's launch, Upside.com provides service to and from all U.S. commercial airports, with round-trip travel originating in the U.S. domestically and to more than 60 international destinations. It also includes more than 1,000 hotels including all "business quality" brands.

The basic idea is win-win for you and your employer. Your employer pays less than it otherwise would and you get a gift card. And the gift cards are real: values start at $50 but can go up to $500 on some trips, and they're with real-world retailers such as Amazon, Home Depot, Whole Foods, Target, and dozens of others.

Upside.com says you still earn frequent flyer credit on flights and charge credit on your credit card, but my take is that you will probably not be able to earn hotel reward credit or take advantage of direct-booking bonuses such as free Wi-Fi.

Although the announcement lyrics don't say so, it's pretty clear that most of the squeeze goes on the hotels rather than the airlines. In fact, the new system, like Priceline, gives hotels an opportunity to troll for cost-sensitive travelers without openly cutting rates. In support of that supposition, I found that the hotel options on a test trip to San Francisco, while perfectly OK, were not on the expected "A" list of options.

Of course, you don't have to go to Upside.com to find bundled air/hotel pricing. Most airlines do it; Allegiant has been making a living on it for decades. You can certainly search and book bundled deals yourself. But the gift card possibility means that you might do better working through Upside.com.

I haven't figured out if there are any special ways to game this system beyond taking advantage of whatever it offers. I'd love to hear from travelers who have tried it.

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Consumer advocate Ed Perkins has been writing about travel for more than three decades. The founding editor of the Consumer Reports Travel Letter, he continues to inform travelers and fight consumer abuses every day at SmarterTravel.

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