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

Airplane at Sunset
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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.

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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 Airfare.com, 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.

Choose Your Time Wisely

You may have no choice of dates if you’re travelling for business or an event, but if you’re travelling for pleasure, the Internet can help you pinpoint the most affordable time to fly. To start with, research “shoulder seasons” for your destinations, which are the lulls in-between hot travel seasons when rates on everything from airfare to hotels drops. September and October typically fit the bill, right between the madness of summer travel and holiday travel, but depending on your destination, different months may apply. Colorado ski resorts might get packed during the winter, but you won’t see quite as many people lining up to visit the Windy City during those months. Google is your best bet for finding prime time.

SkyScanner.netTo narrow your trip even further, use SkyScanner.net, which will actually break down flight prices into a bar graph for the entire month, letting you pick the days with the lowest fares.

Buy in Low

Even after you’ve picked the cheapest time to actually travel, picking the cheapest time to actually book your tickets can be another matter of confusion. In general, cutting it any closer than two weeks on airfare is a major gamble, says Heidrich. But booking further out, the market forces that control airline flights can seem as unpredictable as the ones driving the DOW: Some fares fluctuate hundreds of dollars in days. Microsoft’s Bing travel search tries to accommodate with Farecast technology, which uses previous data to predict whether you should buy immediately, or wait for it to drop within the next seven days. It delivers a confidence meter in its own predictions, and even if you don’t trust it at all, you can use the same service to view historical flight price data and cook up your own predictions as to where things are headed.

PricelineGo with the Flow

Flexibility can pay off big time for less picky travellers who don’t care exactly when they arrive somewhere, or which hotel they plant their bags at, as evidenced by sites like Priceline and Hotwire. Both offer rates well below average, but you won’t be exactly sure what you’re booking before you get it. If you’re looking for a hotel, that means you merely choose the number of stars and the area of town you want to be in, and if you’re looking for a flight, you only get to choose your dates – not the time or number of stops.

Heidrich believes it usually makes a lot more sense to use these services for a hotel than in a flight. “You know what you’re getting with a hotel,” he says. “With a flight, who knows what routing it’s going to take. Who knows if it’s going to be the times of day you need. It just makes planning much more difficult.”

But don’t let that deter you, especially if you have more time than money. “There’s very little risk,” says Heidrich. “If you don’t get it, you can either try again, or you pay what you would have paid through regular means.”

More intrepid bargain hunters can also scratch up clues to get a better idea what lies on the other side of a bid. BetterBidding serves as hub for users of both Web sites, including tips for bidding on Priceline and a running list of participating hotels you might end up with. You can even learn to game Priceline’s bidding process, and view what prices other Priceline customers have booked in your area, to get some idea what starting bid to plug in.

Book Together, Save Together

Sites like Orbitz that offer to roll your hotel, rental car and airfare into one package deal aren’t pulling your leg: Those are legit savings. And it makes business sense. According to Heidrich, the sites offering them get more profit margin on the combos, so they have more room to whittle down the price as an incentive for consumers to snag them.

For example, Orbitz offered us two round-trip tickets from Portland to Rochester, NY for $1,926 when bundled with four nights at a four-star hotel. Separately, the flights would have cost $1,300 and the hotel $734.39, both through Orbitz. That adds up to a savings of $108.39 for one trip, and that’s not to mention the convenience of handling the entire booking through one transaction.

Get Onboard with Twitter

Even if you’ve avoided using Twitter for tweeting the inanities of your own life, it can still be a useful tool for finding bargains. And if you follow them religiously, you’ll be able to respond quickly to the deals that won’t last.

Rick Seaney on TwitterHeidrich recommends following rickseaney, who runs FareCompare.com. “He tweets a lot of deals that no one else has,” says Heidrich. And that includes the all-elusive “mistake fares,” that will let you fly unreasonably cheap – as long as you can snap them up before the airlines catch on. To deliver more regional fares relevant to your home airport, Seaney also runs separate Twitter accounts like flyfrompdx, flyfrommia, and flyfomlax that feature only deals relevant to those airports.

The airlines themselves also run Twitter accounts with some of their most deeply discounted deals. Check out JetBlue, United and Virgin.

Stay Alert

The best deals can come and go in the blink of an eye – and they may never crop up on your Orbitz searches. Many airlines offer special one-off and last-minute deals through newsletters, but unless you want to spend an hour combing through inbox every morning for the good ones, you’re going to need some automation. Fortunately, just as some sites will help you sort through regular airline fares, another batch of specialty sites will help you spot and jump on the hot deals.

Airfarewatchdog.com allows you plug in your home airport and view a list of hot deals right on the spot, and it will even send you a fare alert when a trip you’ve specified interest in reaches your magic price level. TravelZoo offers the same type of interface, but goes a step further. “It’s not just flights, it’s packages,” says Heidrich “All-inclusive trips to Mexico, cruises, and all this stuff.” And the site’s newsletter highlights 20 of the hottest deals every week. The Deals section of BootsnAll operates the same way. And you don’t actually have to book through any of the sites directly – they just hand you off to the company offering the deal.

It’s Not Over Until It’s Over

Even after you’ve booked your tickets or room, you still have the opportunity to save money. How is that even possible?

Refunds. If you accidentally booked at a less-than-ideal time and the fares plunge in coming weeks, some airlines will actually refund you the difference. No reasonable human being wants to check prices on a flight they booked every day just to see if it dropped $20, but with the help of Yapta, you don’t have to. Yapta will monitor your flight and send you automated alerts if and when the price drops on it, giving you an opportunity to hop on the phone with your friendly airline customer service representative and get that refund in the mail. Keep in mind: most airlines offer travel vouchers for your next flight on that airline, meaning you’ll need to fly again with them to realize the savings.

Looking for cold, hard cash instead? Orbitz will automatically cut you a check with the difference if another customer manages to book the same flight or hotel for less as part of its Price Assurance guarantee.

Trust No One

Agent Mulder had it right. Although sites like TripAdvisor make a fantastic stop to scope out potential hotels prior to going, they’re littered with false and misleading reviews, so don’t let a few bad ones scare you out of a two-star hotel and into a five-star that costs $200 a night more. It might even be the folks behind the desk at one hotel ripping on the guys next door.

“When I’m reading a review, I’m always trying to see if that’s something I would actually say,” says Heidrich. “If it seems a little bit too good or a little bit too bad, just discard that one and move on to the next one.” Some sites also let you view a profile of the reviewer, which can be telling. If he or she only has a review or two, don’t weight their criticism or praise too heavily. In some cases, it might even be one hotel planting fake reviews on other hotels, something that TripAdvisor has actually admitted happens within the system. And don’t forget that the most agitated customers are always the ones most likely to log on and rip a hotel to shreds, whether that’s representative of the general experience or not.

Nick Mokey
As Digital Trends’ Editor in Chief, Nick Mokey oversees an editorial team covering every gadget under the sun, along with…
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