Best Online Travel Deals 2009 and 2010: How to Save Money By Booking Online

Airplane at Sunset

Travel expenses add up. Between airline tickets, hotel rooms, rental cars, and three square meals out on the town a day, it’s tempting to give it up entirely when money gets tight.

But you don’t have to scratch that surf trip to Maui in favor of the Jersey shore just yet. With the near omniscience of the Web a mouse click away, finding cheap deals and ways to slash costs on your next vacation (without packing three dozen bologna sandwiches into a cooler as your sole source of sustenance) has never been easier.

We sat down with Chris Heidrich, co-founder of the independent traveller’s resource BootsnAll and the guy who always books the cheap tickets you wish you had seen, to find out how to harness the black magic swirling within the Web and parlay it into travel bargains.

Here’s how to get out of Dodge without having to sell your Dodge to do it.

Aggregate the Aggregators

Everyone has heard of sites like Expedia, Orbitz and Cheaptickets, which take the legwork out of finding the cheapest airline by searching them all for you. But while one might turn up a ticket for $252, the next might best it with $234, leading to a new dilemma: You need to check out multiple aggregators if you want to find the cheapest ticket.

Kayak and MomondoFortunately, some sites take yet another step back and actually aggregate the aggregators for you. Kayak, for instance, will scour all the airlines on its own, but also redirect you to, Hotwire, Expedia, Travelocity and Priceline, all with one click. “It usually gives a really good overview of what’s available,” says Heidrich, who makes it his first stop. For the ultimate lay of the land, CheapTicketLinks, an offshoot of BootsnAll, allows you to enter your departure days and airports, then jump to a dozen other aggregators, including Kayak.

For flights outside the United States, Heidrich recommends the Danish site Momondo, which scans more airlines and sometimes offers more competitive rates.

Cut Out the Middle Man

Sometimes, aggregators offer more competitive rates than airlines and hotels themselves publish on their sites, but it’s always worth your time to check their sites directly before using a third-party site to make sure. In some cases, you might be able to cut out booking fees, and even if the rate ends up being the same, you have one less company to deal with if you need to make any changes to your plans, or have any questions.

Heidrich recalls the time he mistakenly booked a rental car for the wrong days through a third-party site, and called them to try to change the dates. Their answer: Sorry. “No refunds, no trade backs, do not pass go,” he says. “I was just left on the hook.” Had he booked through the rental car company directly, they might have been able to switch the days with little hassle, or even for a small fee, rather than forcing him to eat the entire cost of the mistake.

Go Old School

If you’re dealing with a company directly, don’t be afraid to pick up the phone to wheel and deal, using Internet prices as your first bargaining chip. Hotels especially can show some flexibility on their posted rates.

“Hotels these days are all hurting for business,” says Heidrich. “If you find something online, I would suggest people actually call the hotels and say, ‘I’ve found this online, what can I get it for directly through you guys?’” Even if you don’t end up getting a better price, you might end up getting your choice of room, or other benefits.

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