Planning: Learn to Fly


After you have your passport and have made the 3 Big Decisions and before you start charting where you’ll spend your time and picking hotels, pull the trigger and book your flights. “But I need to figure out all the other details first,” you say. “Pish posh,” I reply with an English accent, “we’re planning not dreaming.”

Time to buy your tickets. No, you didn’t flip too far ahead in the guide, it’s really time. Waiting for your whole trip to be planned until you look for tickets usually results in the trip being put off. The plane tickets can often be the most expensive part of travel- ing and, if they’re the last thing you figure out, the sticker price may wreck all the plans you’ve been making. But if you buy them first, you’ll have a strong grasp on your budget and you’ll know where you can splurge and where you have to save. We also want you to lock into your trip. Take that leap off the cliff, then you won’t dilly dally when it comes to putting the rest of the everything else together. For our part, we want to help you get the most affordable plane tickets available.

When it comes to booking tickets, you have three options available to you (and a few tools that help leverage those options).

Online Travel Agencies (OTAs)

Let’s start with the most popular. Orbitz, Priceline, Expedia, Kayak, Hotwire, you’ve probably heard people rave or complain about each of these websites at some point. They’re robo-travel agents. They all do pretty much the same thing, just with their own special features thrown in to make it exciting.

Each of these agencies has relationships with the Airlines. They’re told how much tickets are and then they turn around tell you. Sometimes the airlines will give a specific OTA a deal on certain fares. Other times, OTAs will sell fares below cost in hopes you’ll book hotels or rental cars through them.


  • Easy to search and compare different airlines

  • Sometimes the lowest fare

  • Able to book individual legs of a trip with different carriers


  • 24 hour cancelation window not guaranteed

  • Customer service varies

  • Occasionally can’t book at advertised fare

Direct Booking with Airlines

Going directly through an airline to book a ticket takes away a lot of the uneasy feelings dealing with a 3rd party can create. You’ll need some good tools to make the most of it (we’ll talk about that next), but you’ll probably feel a whole lot more secure about the process. This is definitely our preferred booking method.


  • Immediate ticketing

  • Reliable customer service

  • You can cancel within 24 hours for a


  • Not always the cheapest

  • Each airline’s routes vary

  • Need to use a search engine to guaranteed refund make comparisons

Search Engines

Google Flights has transformed the way we book our airfare. The search inputs are the same as you would find anywhere: departure and return dates, number of passengers, any specific criteria you have. You’re given results for a wide array of airlines that can be sorted easily by price or number of connections.

After reviewing those flights, you’ll want to click on the calendar option at the top of the screen. This will bring show the lowest price airfare for the days surrounding your departure. You may be surprised to find out you can save $300 just by changing your departure day to a Tuesday instead of a Monday. You may also notice a swing week to week. This is where being flexible with your plans pays off.

You can also sign up for alerts for specific trips and Google will email you when fares drop. When you’ve found a fare you like, you click a link that takes you directly to the airline’s website and you book through them. Kayak and Hipmunk are similar search engines.

Fare Alerts

If you didn't have anything to do all day, you could sit around surfing the airline sites looking for price drops and mistake fares to your favorite destinations. But we’ve all got real lives. All of us that is, except for the employees at fare alert companies like Scott’s Cheap Flights.

They crawl the web each day looking for good deals and screw-ups on the part of the airlines and then send them out in emails. And the things is, they’re really good at it. For Scott’s, you can sign up for the free alerts (why not?) or pay a modest fee for a year-long subscription. We always tell people to just pay for it. If you plan on going overseas more than once in a year, we think it’s a no brainer, you’re gonna save money with this company.

Scott’s isn’t the only name in the game, they’re just the best right now. There is also Secret Flying, Airfare Watchdog, and The Flight Deal. If you’re the kind that likes to get on every list, go for it. But we’re also advocates for keeping it simple and that’s why we’ll give you the following bottom line for booking airfare after just one last tip.

What kind of traveler benefits most from signing up with Fare Alert companies? The spontaneous ones. We’re not necessarily talking about the person who is going to call in to work sick and hop a flight for Hawaii, but more so the person that says, “Rome in the Spring? Why not,” and clicks to book themselves a seat. If you’re flexible about your destination, just looking for whatever adventure comes your way, you’ll be inspired by the deals you find.

The Points Game

Most airlines have points programs in which you earn points for the dollars you spend and the miles you fly with their airline. And almost all of their programs have a partner credit card that will give you points for every dollar you spend using the card. To some people, points are a way of life. They do all kinds of things we would consider a little bit crazy in order to earn them. And if we’re honest, we went a little points crazy ourselves back in the day, but we’ve settled down since then. We consider points another tool to be used for booking direct with airlines. If you’re interested in exploit- ing points to their fullest potential, check out sites like: Upgraded Points or The Points Guy.

Our advice with regard to points is, everything in moderation. We think it’s a good idea, if you’re planning a big trip, to get a credit card with the airline you’ll be fly- ing with and use it to pay for as much as you can related to that trip. That way, you’ll get a bunch of points that can be used to book award travel for future trips. Also, most of those cards have traveler perks like free checked baggage and no foreign transaction fees.

For us living in Phoenix, an American Airlines hub, we like the Citibank AAdvantage card. It’s probably not a good idea to get a bunch of airline cards and rack up a bunch of debt, just for some points. Realize that the reason credit cards can afford to give away a lot of airline points is because there’s lots of people out there paying interest on cards. Try not to be that person.

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Tips, PlanningStephen Reed