The Wanderland Guide to Travel Planning: Booking Flights

Welcome to my newest series, The Wanderland Guide to Travel Planning. This is the second post in a multi-part series, and it’s brought to you by KAYAK. Happy planning!
.

So, you’ve decided where to go. Unless you’re boat or train-bound, or you’ve got a set of wheels and a destination within driving distance, you’re going to have to hop a plane to get where you’re going.

Part II // Flights

If I’m weighing up a few different trips, the price and convenience of flights can often be what tips a destination in my favor (two years ago, for example, I tacked on a side trip to San Francisco from Los Angeles when a quick iPhone flight search revealed a $60 one way fare.) Booking flights is probably one of the most stressful aspects of travel planning, but new tools are starting to make it bearable. Here are some of my tips, tricks, and findings in the world of airfare.

A // Finding Low Fares

• Where to Look: I use KAYAK when searching for international or domestic flights. For domestic flights I also check Southwest directly as their itineraries don’t appear on booking engines, and they are my favorite US airline (hello two free checked bags!). For remote destinations I use Google (simply typing “____ to ____ flight” into the search bar) to double check what low cost carriers fly the route, as they too might not appear on booking engines.

• Search Secretly: Rumor has it that searching for flights in an incognito browser window can save you cash. The theory is that sites that store cookies (basically, save your information) will see that you’ve been looking for a flight and jack up the price the longer you wait, and by searching incognito you’ll get the best deals. Some say it’s a myth, but hey — no harm in trying, right? In Firefox, you can search incognito by going to File > New Private Window. In Chrome, File > New Incognito Window.

• Frequent Flyer Miles: Sign up for a frequent flyer account with every airline you fly, just in case. Yet try to pick one major alliance (there are three: Star Alliance, oneworld, and SkyTeam) and be loyal to the airlines within it. Personally, I build miles with American Airlines, a member of the oneworld alliance, and with Southwest, which has its own loyalty program. Being loyal and sometimes paying a bit more than the lowest fare in order to fly with your preferred alliance pays off. Not only can you use your accrued miles to book free flights, but you can also earn status that will allow you free checked bags, premium seat choices and other perks.

I chose to consciously start flying with oneworld whenever possible because they have a great redemption deal on a flight I take frequently, New York to Bangkok. I haven’t paid full price for that flight in years — instead of $700 for a one-way flight, I pay 35,000 miles and $70 in taxes. And bonus! When you book with frequent flyer miles, you can change to a different time and date without paying a change fee. This allows me to stay flexible when I’m booking long international adventures. Read on to the next section for more on my adventures in travel hacking…

• When to Fly: In general, I’ve found it is cheaper to fly midweek than over the weekends. But the exact dates vary, as do the savings. KAYAK’s new Travelhacker interactive map (go click around, I dare you not to become obsessed) shows the cheapest days of the week to depart and return to each continent according to data analysis of lowest airfares from the US and Canada. It also shows the median airfare for round-trip flights to that region. Using KAYAK’s multi-day search tool can also help you score the best deal if you have some flexibility in your departure days. When my friends flew to Martha’s Vineyard from New York for Memorial Day weekend, that very tool saved the trip — while flying Friday to Monday was a no-go at well over $1,000, they realized flying Saturday to Tuesday was a much more reasonable $300 without so much as opening a new tab.

• When to Buy: It depends on where you’re going. The same KAYAK Travelhacker guide mentioned above also tells you the average number of weeks or months ahead to book in order to get the best deals. Some travelers get crazy enough to research the best time of day and day of the week to book — and I’m one of them! In general, I aim to book flights on Tuesday or Wednesday, when research shows fares are lowest.

Once you’re searching, on certain routes KAYAK’s price forecaster predicts whether airfare is likely to rise if you wait. It’s a super handy tool and it often pushes me over the edge towards pressing purchase or being patient. If you want to keep an eye on prices without remembering to check each day, KAYAK allows you to set daily or weekly fare alerts straight to your inbox as well.

• Picking Seats: Personally I’m pretty easy when it comes to picking seats while traveling alone — window seat if I want to sleep, aisle if I want to stay awake. Less height-challenged travelers can dissect their options at SeatGuru to evaluate where they’ll get the most bang — or legroom — for their buck. If I’m traveling with someone else and there’s plenty of seats still available at seat selection, I’ll reserve us the aisle and window seat. Singe travelers are unlikely to choose the middle seat unless forced to, so chances are you’ll end up with a row to yourself. If not, the single traveler between you will likely be overjoyed to switch to either an aisle or middle. If I’m flying with Southwest, who doesn’t pre-assign seating, I set an alarm for twenty-five hours before departure so I remember to be ready the moment check-in opens and nab myself the best boarding position.

• Agony index: I used to book the cheapest flight no matter what, layovers be damned. I still do if I see a deal I can’t beat, especially when I’m cashing in frequent flyer miles. But in general I try to remember that I might spend just as much eating and entertaining myself over a long stopover as I would have to have flown a more direct route. Don’t forget to factor that in.

B // Gaming the System

If you’ve yet to hear of travel hacking, prepare for a whole new world to open up to you — a world I’ve only started to dip my toes in. Travel hacking comes down to accruing points and miles and redeeming them in an effective way, resulting in free travel. You can accrue miles and points the traditional way, by being loyal to a single airline alliance or hotel family, and you can earn them through credit card points.

These days, I vary rarely pay full price for a flight — instead, I use miles and points. Right now, I’m not building points with any hotel group though I do have large banks of miles with the airlines mentioned earlier in this post. Yet I earn the most miles when I’m not even in the air, thanks to credit cards. Over the years I’ve flirted with various hotel and airline cards with big sign up bonuses in order to boost my number of hotel points and frequent flyer miles, but in the end the cards I’ve stuck with are the ones with a purchase eraser feature. Such as…

The Capital One Venture Card or the Barclaycard Arrival (both with no foreign transaction fees, of course). Both cards offered high sign-up bonuses on approval that helped me earn free travel fast! Both cards also allow me to book any flight on any search engine, and use the points I’ve earned (two points for every dollar spent) to “erase” that flight off my credit card statement. It doesn’t have to be flights, either — I’m just using that as an example, but it can actually be any kind of travel purchase, from hotels to train tickets to even cabs. For example, a $100 flight will cost 10,000 points, which it cost me $4,500 to earn. (Every time you redeem, you get 10% miles back to use toward your next redemption — so it would really only cost 9,000 points, or $4,500 to get that free $100 flight.)

Not bad for money you’d spend anyway!  Yet the real benefit is in the initial sign up bonuses, which each yielded me $400 in travel credit. Worried about meeting the minimum spend to nab that bonus? Time your sign up to align with a big purchase you’re already making, like buying a laptop or booking a major flight. And don’t spend a dime in cash unless absolutely necessary — I charge absolutely everything in order to boost those points up as much as possible. There are entire blogs dedicated to the art of travel hacking, so clearly this is only the briefest taste of what you can do. If you’re interested to learn more, you can read in depth about my travel money management system here, and you can read a great intro to travel hacking here.

C // At the Airport

• One Way Tickets: Some international destinations require you to show a return ticket out of the country or the region when you check in for your flight. This can be an issue if you’re on an open-ended, multi-country trip in which you plan to travel overland. I know more than one person who’s been forced to buy a return flight at the gate or be denied boarding. Getting asked to show your proof of exit can come down to luck, though I think looking well-put-together at the flight check in counter and going through immigration doesn’t hurt your chances of getting through hassle-free. But don’t leave it up to chance — research how strict your destination is and what they’ll accept as proof of exit. Can you show a plane ticket out of the continent? A bus ticket out of the country? Can you apply for a visa ahead of time instead? Can you get crafty with Photoshop? (Just kidding on the last one! (But actually not at all kidding.))

• Airport Apps: GateGuru is my go-to once I’m at the airport thanks to terminal maps and restaurant lists filtered by terminal and sorted by gate. Never again settle for Sbarro only to learn there was a Chipotle around the corner! Looking for a lunch date? Check Stopover to see who else is around.

• TSA Pre-Check and Global Entry: Global Entry and TSA Pre-Check are programs that can make your life at the airport a lot easier through expedited screening and dedicated lines. Last year, I applied for Global Entry (GOES). It cost $100 for five years, and after a lengthy application and an interview at JFK airport, I was granted a Trusted Traveler number that allows me to sail through special Global Entry lines and kiosks when re-entering the US from abroad. When I signed up I was actually primarily interested in the fringe benefit of being auto-enrolled in TSA Pre-Check. TSA Pre-Check is never guaranteed, though when I enrolled in Global Entry I was told to expect it 80% of the time.

Lately, it’s never coming up, and on my last domestic flight a sympathetic TSA agent explained that with so many travelers now enrolling in these programs, Pre-Check is being reserved for those that have paid directly for it, and no longer ushering in elite status frequent flyers or Global Entry members who have received Pre-Check consistently in the past. Bummer. I suppose now I’ll have to also enroll in TSA Precheck, which costs $85 and also requires a lengthy application and an in-person interview.  Still, I’d say it’s worth it for five years of dedicated Pre-Check security lines, leaving on your shoes and jacket on, and keeping your laptops and liquids in your bag!

• Be nice: Didn’t get the seat you wanted and hoping the gate agent can adjust it? Running late and hoping to beg your way to the front of the security line? You better slap on a smile. I can’t tell you how many times I’ve narrowly made a flight due to the help of an airline employee or my fellow passengers, and it’s because I have a strict motto: It’s my problem, not theirs. About to miss check-in time? “Hi, I know I’m checking in ridiculously late and I have no one to blame but myself for this. Is there any way you could help me make my flight today?” Hoping for an aisle seat? “Hi, I know that this flight is pretty booked and you’ve got your hands full, but if there’s any way I could be switched to an aisle seat it would really make my day.” Humor, kindness, and self-deprecation will get you a lot further than hysterics. (Except when it comes to the TSA. Literally nothing will get you anywhere with them. And yes, I’m still bitter about my water bottle.)

Stay tuned for Part III of this series! What are your best flight finding tips? .

Still have more travel planning questions? Sound off in the comments and let me know what’s on your mind, or follow KAYAK on Twitter (they’re quick to answer booking questions) and check out their #TravelProblemSolved page!