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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.

Flight Booking Tips

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.

Flight Booking Tips

• 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.

How to Book Flights

• 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.

How to Book Flights

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.

Flight Booking Tips

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.))

How to Book Flights

• 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.)

How to Book Flights

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!

  • Ellie Quinn
    October 9 2015

    Loving this new series!
    I’ll have to check out some of those apps, although is Kayak mainly aimed at the US or worldwide?
    So true about booking a cheaper flight with a long layover and how it may end up costing more in food ect. I think that about early morning/late night flights, if you have to get a taxi to the airport because public transport isn’t running you’re often better paying more for a flight at a decent time!

    I also wish we had all these frequent flyer miles in the UK, we just don’t have as much as the US at all!

    • Alex
      October 10 2015

      Kayak is worldwide! I used them to book my entire Europe trip last summer and I didn’t find better prices anywhere. And good point about public transportation. Luckily the Skytrain and the subway run 24/7 in NYC, so it’s easy to reach JFK anytime of day!

      • Ali Butt
        February 20 2017

        Can u tell me please how can I get the Tomorrowland ticket and all procedure?

        • Alex
          February 27 2017

          Hi Ali! You can find my Tomorrowland ticket-getting tips here. Hope that helps!

  • Pilar
    October 9 2015

    Dear Alex, check
    I cannot leave without it and I travel for work 5 days a week!
    Have a great time in Koh Tao xxxxx

    • Alex
      October 10 2015

      Wow! Awesome site — I’ve never heard of it before but just had a lot of fun playing around with it. Thanks for the tip!

  • Shaun's Cracked Compass
    October 9 2015

    Really enjoy hearing your process Alex! Like Ellie, travel rewards in Canada suck, big time! I’m a little jealous of all the choices yanks get.

    Kayak & google are my go-to searches for flights. And the cookie monster is real. I’ve noticed that as I look for flights they tend to tick up, I clear my cache & cookies, same price I originally searched for comes back… in most cases.
    Shaun’s Cracked Compass recently posted..Have you been on an airplane before?

    • Alex
      October 10 2015

      You might not be able to gain points with credit cards, but you can always build the old fashioned way with frequent flyer miles 🙂 I am so grateful so the credit cards though, it’s saved me thousands over the years.

  • LC
    October 9 2015

    Thanks Alex, wonderfully thorough and in-depth (as always). I’m endlessly envious of the American travel points system!

    • Alex
      October 10 2015

      It’s definitely a bonus if you play your cards right (pun intended!) But you can always build points with a frequent flyer number the ‘ol fashioned way, wherever you live.

  • Luda
    October 9 2015

    Awesome series, looking forward to reading more! I totally second the deleting cookies/going incognito tip … I did this while looking for a cross-country flight recently and saved about $50!
    Kayak is also one of my first choices for finding flights– their package deals are great 🙂
    Luda recently posted..Weekend Updates: Cal Academy & Souvenir Shopping

    • Alex
      October 10 2015

      Nice! That’s not bad for opening a new window 🙂

  • Tamara
    October 9 2015

    So many great tips in here! Thanks!!

    • Alex
      October 10 2015

      You’re so welcome Tamara! Glad you found it helpful!

  • Naomi
    October 10 2015

    Really liking the new series! I’ve been using Kayak for years but I didn’t know anything about all these new features. Yet another reason for me to love Kayak!
    Naomi recently posted..Workouts for girls on the go (guest blog by Quinn Vaccarino)

    • Alex
      October 13 2015

      I’ve been loving them for years too! Which made it very exciting to get to partner with them 🙂 Glad to hear they have so many other fans here!

  • Britt
    October 10 2015

    I’m kind of addicted to travel hacking. The programs aren’t as good here in Australia but I still managed to accrue enough points to get a business class flight to Europe for my trip starting next month. I’m almost most excited about the flight than anything else!

    In terms of one way tickets. If its a destination served by Qantas they have a fully flexible ticket that you can cancel at any time for a complete and free refund. It’s pretty expensive (about double a normal ticket) but I don’t really care because I know I’m going to cancel it anyways when only buying the ticket to prove I’m returning. Once I enter the country I cancel it and get my money back.
    Britt recently posted..The Proud Peacock (Melbourne Food Review)

    • Alex
      October 13 2015

      Ahhhh that’s amazing Britt. I’ve yet to hack a business class ticket — you’re my hero!

  • Jenia
    October 10 2015

    We used to do Chase Sapphire and just switched to Capital One only because of the annual membership fee. It’s kind of a pain to switch every year, but the travel miles bonus (40,000 miles just for signing up!) is a whole lotta travel miles that makes it worth it. 🙂
    Jenia recently posted..Belgrade’s Warring Identities

    • Alex
      October 13 2015

      Indeed it is! I tend to have a few cards going at once but usually apply for a new one and cancel and old one once a year.

  • Kristina
    October 10 2015

    Thank you so much for putting in the time and effort to write these posts that are so helpful!
    I’d love to hear more about how you decide what to see once you get to your destination and how you plan an itinerary. I know you read a lot of guidebooks so how do you decide what to see and what to skip from all the information out there! And how do you deal with FOMO?
    Second, how do you manage your cell phone and other life details like medication when you’re always on the go?
    Also would love to hear about your tips and tricks for working on the road. I’m overly sensitive to my working environment and don’t tend to be productive when there is a lot going on around me. How do you adjust to constantly changing working environments?

    • Alex
      October 13 2015

      The first two questions I’m definitely going to be addressing throughout this series! The last one I think is a different topic, but I’ll keep it in mind for future post ideas 🙂

  • Dominique
    October 11 2015

    I’m so bad at travel hacking! I always apply for new frequent flyer programs only to never use them again! I’m always impressed when people are able to fly on their points! It’s a goal I’m working towards, maybe I should try using credit cards to save points… Thanks for the tips I’m looking forward to the next article!
    Dominique recently posted..Abu Dhabi – Islands and Views

    • Alex
      October 13 2015

      You’re so welcome Dominique! Hope it helps you get that free flight faster… the first one is always the best 😉

  • becky hutner
    October 11 2015

    Man, I would be PISSED if I’d settled for Sbarro only to run into a Chipotle. In fact I was pissed after my last airport Sbarro meal full stop!
    becky hutner recently posted..Fashion ‘Round the World: WINTER ’15

    • Alex
      October 13 2015

      Yeah, it never quite hits the spot, does it? Chipotle in an airport is like striking gold!

  • caroline
    October 13 2015

    Oh man! I love this. I was just looking for a trip from florida to va for christmas- literally flying out xmas eve. the best I could find via skyscanner was 400. I looked through my credit card reward’s website and before my lame $50 discount, I found one for about 250! No free checked baggage though- I didn’t know that about SW.

    Cant wait to test out Gate Guru! I have two trips coming up I can use that on! thanks for the tips 🙂
    caroline recently posted..giants causeway, northern ireland

    • Alex
      October 13 2015

      You’re so welcome Caroline! May you find the best dining at the optimal location to your gate 😀

  • Erika
    October 13 2015

    I love the Barclaycard Arrival!! I use it for all my day-to-day expenses and it has made travel so much more accessible for me! I haven’t gotten any more into travel hacking than the one card, though — I know a lot of travel hackers can have dozens of credit cards at once, but that just seems like too much to manage for me!
    Erika recently posted..Pumpkin Spice Popcorn and a Scary Movie Marathon

    • Alex
      October 15 2015

      Yay! Makes me so happy to hear a success story like that, Erika. Kudos to you. Yeah, I typically keep three cards at once… and even that gets hard to juggle!

  • Leigh
    October 19 2015

    I love what you call “agony index” – I have a friend who will pick a 28 hour itinerary involving planes, trains and buses just to save 50 bucks!

    I actually had the reverse happen to me while planning my first trip to Asia – my options to Chiang Mai were a normal layover in Seoul for $1200 or a 20 hour layover in Hong Kong for $800 – so now I get to spend a day in HK and even with a $200 hotel room, I’m coming out ahead!
    Leigh recently posted..My Review of Grand Canyon Rafting – Lees Ferry to Whitmore Wash

    • Alex
      October 23 2015

      Nice! I’ve been able to visit both Singapore and Bahrain for the exact same reason — layovers that were the cheapest option. It’s the best!

  • Marie
    October 29 2015

    I never thought that booking a flight can be hacked.. LOL! Remind me next time to use my credit card when booking please. Damn, I missed a lot of points already. Thanks for this awesome guide.

    • Alex
      October 30 2015

      Don’t let that stop you from getting started! I used to be so annoyed at all the points I’d missed out on and let that derail me from really getting started with it. It’s never too late to get going.

  • Aaron Jade
    October 31 2015

    Hi Alex, great tips. I must start getting into the credit card airpoints schemes, may as well be getting some benefits from using it all the time! Aslo love to use kayak, you can easily get all options on one search instead of using multiple websites. Happy travels.
    Aaron Jade recently posted..Sunset Over Fuengirola Coastline

    • Alex
      November 2 2015

      Kayak is the best! And yes, it always feels good to earn a little something back from all the travels.

  • Claire
    January 6 2016

    If a long layover is unavoidable, take advantage of it and get out of the airport! Not all airports are near enough to fun places to make it worth it, but I have had some great layovers! We couldn’t avoid the 10 hour layover in Fiji when we were on our way to Samoa, so we visited a beautiful Hindu Temple and rode the bus like locals. On the way home we had 9 hours in Honolulu, and we spent most of that time at Pearl Harbor! This spring I am heading to Paris and I am excited to be spending my 8 hour layover in Copenhagen by seeing a few sights and eating new and interesting foods.

    • Alex
      January 7 2016

      Indeed, Claire! I visited both Singapore and Bahrain on 24 hour layovers. They were amazing experiences and I’m so grateful my flight plans brought me there!

  • Kristina
    January 28 2016

    I meant to share this tip a while ago, and totally forgot. Another way that I find low-cost carriers or more obscure domestic airlines is to go to the Wikipedia page for the airport(s) you’re considering. The Wiki site almost always lists all the airlines that fly in/out of that airport. Another alternative is to go to the airport’s actual website, although I find that the user-friendliness of these sites varies dramatically.

    • Alex
      February 1 2016

      Yup, that is a great one! I have found some bizarre little airlines that way! You can also just google “Direct flights from [insert airport code here]” and get so much info.

  • Natasha
    May 9 2016

    Great advice, Alex! I saw a couple of comments about “wishing I had known that sooner”…Like you, I sign up for every frequent flier program and try to stay within a n alliance if I can. I dont have credit cards but I do have my debit cars linked to United mileage Plus, so if I happen to dine out and use my card I often get points for that. But I would suggest to people who are signing up for flier programs -READ THE FAQS & program terms. Sometimes flier programs will award miles if you have flown with them previously within that year but werent a member yet. As long as you have your boarding pass/confirmation info, usually there is a form on the website where you can submit the information and request mileage credit.

    • Alex
      May 18 2016

      Indeed! If you forget to put it in while booking you definitely still have a window to get those miles after!

  • Bruno @ Geeky Explorer
    September 12 2016

    Great tips here! I didn’t know GateGuru and I always forget to check Seat Guru, such great tips there.

    I just get frustrated with airline miles. I wish the miles programmes in Europe were as advanced as in the US. Do you have any recommendation?
    Bruno @ Geeky Explorer recently posted..How To Find Cheap Flights To Anywhere In The World

    • Alex
      September 14 2016

      Hey Bruno! I actually think frequent flyer programs across the board are getting more and more useless, sadly. As more airlines switch to dollar-based accrual rather than mile-based, they will slowly become obsolete to all but first class flyers. Bummer! These days I focus more heavily on building credit card points!

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