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The hassle-free holiday flying guide
With fewer flights, more fees and a 20%-to-40% hike in fares, you need a serious strategy.

By Carolyn Bigda and Donna Rosato, Money Magazine
October 14, 2008: 5:24 AM ET

airport_hassles_stock(Money Magazine) — Santa’s got a good thing going travelwise, what with that high-speed reindeer-powered sleigh that takes him to every chimney on the globe in mere hours – no layovers, no delays and no shortage of under-seat storage. You might want to thumb a ride with the old boy, in fact, because flying the nonfiction way isn’t going to be so jolly this holiday season.

For starters, Thanksgiving and Christmas air fares are up 20% to 40% compared with years past, according to Rick Seaney, CEO of That’s in part because most airlines cut 10% to 15% of their capacity this fall in reaction to fuel prices, which reached record highs this summer.

Fewer flights mean fuller planes, less space in the overhead and a greater chance that a canceled flight will leave you stranded for days. The Scrooging doesn’t stop there, thanks to the bevy of new fees. (Want to check a bag? That’ll be $15. Care for a bottle of water? Fork over two bucks.)

To help you get to your destination with your holiday spirit mostly intact, we interviewed reams of experts and dug up the smartest strategies for every stage of the process: booking cheap(ish) tickets, packing to avoid fees, speeding through security and managing delays. Merry flying to all and to all a good flight!

Stage 1: Book like a pro

Start shopping this Monday. Because of the recent capacity cuts, carriers have fewer empty seats to sell, torpedoing the usual advice to buy tickets at least three weeks in advance. This year aim to book six weeks ahead, says George Hobica, who runs In other words, now. The best time to shop: a Monday or Tuesday, as airlines typically lower fares early in the week and raise them on Friday.

Search the whole Internet. Start with comprehensive fare search engines like and that scour the Web for the best combination of schedule and price. (Just be sure to nix potentially problematic flights such as red-eyes and those involving multiple carriers on one route. Kayak lets you filter these out, but ITASoftware doesn’t.)

Drive, then fly. Fares from small and mid-size cities (think Manchester, N.H., Eugene, Ore. or Bloomington, Ill.) are up more than those from big cities. If you live in this kind of place, it may be worth driving a few hours to a larger airport. Going 120 miles in a 2006 Toyota Camry with $3.80-a-gallon gas will add about $38 round trip – pennies compared with what you may save. Since parking might be more pricey at a bigger airport, go to and check out Park ‘n Fly, a cheap off-site option in many cities.

Fly against the grain. Thanksgiving, Christmas and New Year’s Day will all fall on Thursdays this season. For Turkey Day, as usual, it’ll be most expensive to fly out the day before and return the Sunday after. For the other holidays, leaving on the Friday, Sunday or Tuesday prior and coming back Sunday will be most costly. To get a better price, try adjusting your departure and your return to avoid those dates; you can sometimes save hundreds of dollars that way. Use to see how different travel dates will change the price of your itinerary.

Find the secret specials. Once you find a flight you like, search for it on the airline’s site to make sure you’re not missing a deal. (To reduce commissions to sellers, airlines are increasingly saving the best prices for their own sites, posting specials that search engines can’t pick up.) Also go to the Discount Airfare section on Hobica manually collates airlines’ exclusive Web specials and e-newsletter offers. “A lot of the best deals are unadvertised and short-lived,” he says – such as a recent two-for-one deal on Virgin America and a $399 Denver-Honolulu round trip on Frontier.

Delay-proof your itinerary. With fewer flights, it’ll be harder to get on the next plane out if yours is delayed or canceled (a risk in snow-and-sleet season). Check on-time performance of flights you’re considering at; skip those with bad records. The first flight of the day is generally the best bet, as you won’t get stuck behind other delayed planes. If you have a choice of connecting cities, pick the one with the warmest climate – and avoid those listed in the chart above right.

But prepare for reality. Fly at least 24 hours before you need to be back home, and if you’re connecting, be sure your layover is at least two hours. Before you go, check the Web to find out the time of your carrier’s next flight as well as a similarly timed one from a competing airline. Write them down. If you’re delayed, knowing the alternatives will be valuable when you’re trying to rebook.

Check the odds. For most flights, prices will keep rising as the holidays get closer. There are a few exceptions, however, so once you’ve picked a flight, vet it at, which uses historical data to tell you if the price is likely headed up or down. Unless Farecast is at least 60% confident that it will fall, book now.

Get a good seat. Before you select your seat assignment, go to to find out which seats on your aircraft will be most – and least – comfortable. Also, some airlines, including Delta and JetBlue, allow you to pay for a roomier seat (up to 38 inches vs. the average 31). The investment ($5 to $100, depending on the airline) may be worth it if you’re tall or claustrophobic.

Stage 2: Pack efficiently

If you’re able to carry on…Making carrying on your default option will save you a lot of stress. It’s the only way to sidestep the checked-bag fees that most of the major airlines recently announced (see chart above right). Plus, you won’t have to worry about luggage getting lost, misdirected or mauled by handlers. Worried about wearing the same shirt for 10 straight days? Packing expert Doug Dyment of has mastered the art of getting a lot of clothes into a little space – while minimizing wrinkles.

Pick the right bag. That means soft-sided (easier to squeeze into unforgiving spaces), wheelless (“Roll-on bags can be triple the weight and subtract one-third of your usable space,” says Dyment) and as big as rules allow (most airlines permit 22 inches in length). One that measures up: the Red Oxx Sky Train ($255,, which weighs just four pounds and can be worn as a backpack. Can’t deal without wheels? Consider Eagle Creek’s Tarmac 22-inch, which weighs in at eight pounds ($275,

Fold the right way. Lay each item of clothing on a flat surface, one on top of the other, each piece going in an alternating direction to create what looks like a plus sign. Place an object – like your toilet kit or a bag of socks and underwear – in the center of the plus sign (see Figure 1).

One by one, wrap the protruding end of each article of clothing up and around the core object until you get a round, compact bundle. “This minimizes wrinkles while maximizing luggage capacity,” Dyment says (Figure 2).

Drop the bundle into your bag. Tuck in whatever stray items (book, iPod) remain (Figure 3). You’re ready to head to the airport.

If you’ve gotta check… If you’re considering shipping your bag via a service like FedEx or the U.S. mail to save money, forget it: Checked-bag fees are usually cheaper. The best way to save money is to weigh your bag before you go. That’s because on domestic flights you’ll owe yet another fee – generally $50 or more per bag – if the weight tops 50 pounds. Just hop on your bath-room scale with your suitcase and subtract your weight (no cheating). Heck, maybe it’ll help you think twice about that doughnut at the airport too. If you must check more than 50 pounds’ worth of stuff, divide it into two suitcases: You’ll usually pay much less to check two regulation-weight bags than one overweight one.

Stage 3: Check in faster

Remember the 24-hour rule. To get an even better seat, check in for your flight via the airline’s website a full 24 hours before boarding time (don’t wait for the e-mailed reminder). That’s when airlines release the best assignments, those that had been reserved for elite fliers. Being among the first to check in can also prevent you from being bumped and help you move to the top of the upgrade list. (With Southwest (LUV, Fortune 500), you up your odds of getting in one of the first boarding groups.) And best of all, if you print your boarding pass at home and aren’t checking bags, you can head straight to security.

Get edgy. Make a beeline for the farthest-flung security checkpoint. “Those on the edges of the airport tend to be less used than ones in the middle,” says Mark Ashley, editor of the blog Upgrade: Travel Better ( To determine the absolute quickest line at any airport in the U.S., go to the list from the Transportation Security Administration (TSA) at

Go black diamond. This year the TSA has been rolling out security lanes labeled like ski trails (black, blue and green), meant to separate “expert” travelers from dallying families. Though it’s up to individuals to choose the appropriate lane, the honor system seems to be working. According to the TSA, the black-diamond lanes are 21% faster on average. So far 50-odd airports have the lanes; you can find them at

Swap out your laptop case. New TSA-approved laptop bags allow X-ray machines to get an unobstructed view of your computer without your removing it – saving time and hassle. The Aerovation Checkpoint Friendly Laptop Bag ($130, is opaque black, weighs less than three pounds and is roomy enough for a 17-inch screen.
Stage 4: Negotiate problems

If your flight is delayed… Most airlines won’t do much for you if the problem is out of their control, like air-traffic congestion or weather. But if it’s their fault – a mechanical or crew problem – they may be more accommodating. Delta (DAL, Fortune 500), for example, says that it will provide lodging if you are stuck for four hours between 10 p.m. and 6 a.m.

It pays to know what your airline says it will do, since it may not volunteer such hospitality. Read its “contract of carriage,” which lists your rights, before you travel. Find links at (click on User’s Guide and then on Info Center).

As for making a connection: If you might miss yours because of a delay at your initial airport, alert the gate agent; the airline may hold the plane for you briefly. Or if weather isn’t the issue, ask whether you can go on another flight or through a different hub. Should none of that work and you miss the plane, alert an agent. The airline must put you on another flight, but it could be a while.

If you’re bumped… As you know, when flights are oversold, airlines ask for volunteers first, offering them a later flight in exchange for a trip voucher. If not enough people raise their hands, travelers sans seat assignments, those who checked in last and, on some airlines, those who paid the least, are the first to go. If you’re tossed off, you’re entitled to on-the-spot cash compensation based on how long it takes to get you to your destination.

If your flight is canceled… The second you hear that your plane is a no-go, call the airline’s toll-free number (you have programmed it into your cell phone, haven’t you?). You’ll get rebooked more quickly than at the counter, where one disgruntled airline employee is being swarmed by a mob of disgruntled fliers. Ask what your options are. Most airlines will rebook you, gratis, on their next flight on which space is available. If that requires a long wait, ask the rep to find out whether a competing airline has seats to your destination and, if so, to endorse your ticket to that carrier. You’ll have the most luck if the flight is on a partner airline. Alternatively, suggest connecting through another city or going to another airport.

Andrew Nusca contributed to this article.