How to choose a flight

If you travel with any sort of frequency — or even if you don’t — it’s worth taking the time to learn how to pick flights effectively. Choosing good flights and good seats on those flights can often be the difference between an easy travel experience and a miserable one.

When you fly 100-200 times a year, the argument for taking the time to get good at picking flights this is sort of obvious: every little thing that’s wrong with your week-to-week travel experience adds up fast. When you get on an airplane twice a week or even more, poorly timed flights or dealing with a long (or delayed, or cancelled, or really any) connection can mean the loss of hundreds or even thousands of hours per year.

These things mean less when you fly less than, say 10-20 times per year, but even someone who only travels occasionally should learn how to choose flights too. At that number, you can just deal with inefficient timing and miserable experiences on every single one of those flights, but why would you want to, when a minimal amount of effort can put you on good flights instead?

Having a system by which you pick good flights can make the process of booking travel itself faster, too— you just choose the one that does the best against your criteria. No hemming and hawing about timing or scheduling, waiting a day and then being mad when the price goes up.

Choosing a flight shouldn’t take more than 10 minutes per trip, and it’s worth every one of the ten. What follows is my personal criteria and system for doing this. Yours may be a little (or entirely) different. That’s great. Use this as a starting place and tailor to your needs.

Shop For Flights On Value

Before we get into what makes a good flight good and a bad one bad, I want to explain the most important thing I’ve ever learned about choosing flights:

Never choose flights based solely on price. Choose flights based on value.

Price has a place in the calculus of choosing the best flight, sure, but the best flights usually aren’t the cheapest —nor are they the most expensive.

The best flight is the one that (in order) gets you to the place you want to go, when you want to be there, as quickly and comfortably as is reasonable, priced within an acceptable range. This is true whether or not you’re footing the bill.

If you only choose flights based on “price, lowest to highest,” you give up your right to choose (and complain about) literally everything else, from timing to seats to carrier.

Give yourself more flexibility by shopping on value instead.

If you are traveling for pleasure, this is especially hard, but I have a simple trick for you: put a price on your pleasure.

My price is $150 per round trip plus an extra $25 per hour of additional travel time I don’t have to incur. That is, even when I’m traveling on my own dime, I will spend $150 + $25 per hour shorter more than above the cheapest possible ticket to get a better flight. Whether that’s a better seat, a better airplane, a direct flight, a better time, whatever. The math is completely arbitrary; use whatever numbers make sense to your pocketbook. The idea I’m trying to sell is that your time and comfort also have a price, even (especially!) when you’re traveling for pleasure.

Let’s say you only take one vacation away from home this year, 10 days total. Do you really want to start that vacation miserable and exhausted by waking up at 4AM and then burning 10% of your total vacation time sitting in a connecting airport just to save a hundred bucks?  Even if this hypothetical early morning connecting flight gets you in by the early afternoon, is it really worth $100 in your pocket to be too exhausted to actually do anything by the time you get settled and go exploring?

Remember also to do this math based on the loaded cost of a flight.

From a purely economic basis, the cheapest tickets are almost always on low cost carriers (or more frequently these days, the “basic” offering of major carriers, which are in many ways worse, because at least when you fly Spirit you know what you’re getting yourself into). They often fly into secondary airports from which it takes more time and money to get to your real destination, and, once you add back those transportation costs and the other amenities that you lose and have to buy back a-la-carte (like a carry-on bag), it’s often not even much cheaper.

If you are traveling for work, you doubly shouldn’t feel a need to get the cheapest possible ticket. Spend the extra hundred or two (or three!) to be on your preferred carrier on a good plane at the time that best suits you. It’s a good practice to treat your employer’s or client’s money with respect, but value of you being happy, well-rested, stress-free, and there at the right time — and therefore more effective during your working hours — is worth the additional cost to them.

Again, I’ll just go for the economic argument: whether or not your firm charges by the hour, let’s say your services are ultimately billed to a client at an effective hourly rate of $250/hr. If taking a different flight means you’re able to get two more hours of effective, needle-moving, billable work done at the client (because you’re there longer, or you’re well-rested, or whatever), it’s worth it, even if the flight is $499 more expensive.

Don’t be penny wise and pound foolish.

Pick the best flight

In this context, best means flying on the biggest, newest aircraft possible, without connections. Oh, and avoiding regional jets if at all possible.

There are two main reasons for this: comfort and speed. Big new aircraft have better amenities, more space, more headroom, more luggage room, more comfortable seats, and because they also normally have bigger engines, they will literally get you to your destination faster than a smaller plane.

If you mostly fly one carrier (which you should), take time to learn which planes they fly, which of those are the newest, and which are regional jets, and use this info when picking flights.1 Ever wonder why a disproportionate number of business travelers are lunatic savants when it comes to being able to identify aircraft? This is why.  If you don’t know this information or don’t know where to find it, the answer is the incredibly detailed, and as a backup, All booking sites will tell you what kind of airplane any given leg of a trip is supposed to be on (it might be in an expandable “more info” section). Take a few minutes to cross-reference this with one of the above.

Fly nonstop whenever possible. All connections add time, regardless of the length of the layover. Even flights with well-timed connections can double your travel time once you add in the time it takes to taxi to the gate, leave the plane, walk to the gate, get on the new plane, wait to take off.

The connecting airport is also almost never exactly between your origin and destination, and can even be hundreds of miles out of the way, which also adds time. Add to that the uncertainty of having to deal with delays, cancellations, surprise maintenance, and other unexpected gotchas for not one but two aircraft? Fly nonstop whenever possible.

Fun air travel terminology gotcha: be wary of direct flights. All nonstop flights are direct flights, but not all direct flights are nonstop — direct just means that you can buy one ticket on one aircraft that goes all the way to your final destination. It might actually stop somewhere in the middle to pick up or drop off passengers (in which case, go for an actual nonstop or just a normal layover — you’ll have more flexibility).

If you can’t get a nonstop flight, try to connect through a hub, even if it’s a little bit out of the way. Hubs are more likely to send multiple flights to your destination over the course of a day, and the hour you lose from going out of your way is worth it as a hedge against massive delays and having to stay in that city overnight if your original connection gets cancelled or dramatically delayed.

When given the option, also make sure you’re flying to the right airport for the city you’re going to, avoiding secondary airports that pretend to be in your destination city but actually are far away or have poor access to the city center.

Practical example: if possible, fly into LGA. I know this is blasphemy to most New Yorkers, but I don’t care — LaGuardia is considerably closer to midtown Manhattan than JFK, and unless you’re going at five in the morning, Newark’s geographic closeness will never make up for the traffic nightmares that are the Holland and Lincoln tunnels. LGA is a little run down, sure, but who cares—your primary objective as soon as you enter an airport should be to leave it as soon as possible, not hang around and check out the dining scene in Astoria.2 If you do happen to want to check out the dining scene in Astoria, you should go to AbuQir or Sabry’s. They’re both no-frills but fantastic Egyptian seafood places, which is apparently a thing there. Makes sense, really, considering New York gets great fish and Astoria has a large Egyptian population.

Fly at the best times

In the context of business travel, all of the above considerations (even cost!) take a backseat to when the flight actually occurs. Aside from “a reasonable amount of time before you actually need to get there, in case something unexpected happens,” preferred flight timing is a personal thing.

That said, the goal is always to maximize your amount of productive or quality time on the ground — on the weekend, you want to maximize time at home and with people you like; during the week, you want to be working at the client site, as it’s harder to be productive in transit. This leaves two primary options: flying late, or flying early. Between the two, it really comes down to what you consider good or bad.

The pros of flying late are avoiding the misery of waking up at four in the morning for a 6AM Monday flight. If you’re already a morning person, this shouldn’t be too bad, but many would rather spend an extra night away from home than experience it. If you’re a morning gym person, flying late means you can maintain your routine (always a good thing).

The cons of flying are, well, you get in late. Often very late. Delays cut directly into sleeping time. When late also happens to mean the last flight out, a cancelled flight means you’re not going anywhere until the following morning.

Flying early has inverted benefits: delays eat into working time, not personal time; it’s an opportunity to get an early jump on the week while in transit, and you can spend Sunday evening in your own home watching Game of Thrones (or whatever it is that you do on Sunday night). Plus, you get an extra night in your own bed, although if you can’t nap on planes and want to get enough sleep, this extra night comes with a very early bedtime.

The drawbacks of flying early are mostly around getting up so damn early, sometimes as early as 3:30 or 4:00 in the morning. If you have a regular morning routine, this will be a weekly or bi-weekly interruption to it. Waking up that early can make you a sleep deprived zombie on  Monday, which is always rough, but can be especially bad when it’s your first day on a client and you’re trying to make a good impression.

The most common pattern I see is probably a combination of the two: fly early on Monday and directly after work on Thursday (assuming four days on-site), jumping on the next flight out after their weekly obligations are complete.

You don’t necessarily have to do that, though. For example, I prefer my routine to not be interrupted by travel, even if it means not being home exactly as soon as I possibly can, so I often stay an extra night and fly out on Friday morning, especially if I’m going directly to my home office for a day of work anyway. Make the choices based on your priorities, not what everyone else is doing.

Select the best seats

The best seats in an airplane are as close to the front of the aircraft as possible, on an aisle. Pick these.

The front of the plane is desirable because you can leave the plane faster, and the farther away from the engines you are, the less their rattle and noise will bother you.

The aisle is desirable because you can get up to move around, stretch, or use the bathroom as often as you like. The view from an airplane window really never gets old, but it’s not worth the inconvenience and discomfort of sitting in a window seat.

In the aisle seat, you will have to deal with row-mates needing to pass by you, which requires you to stand up every once and a while, but since you should aim to stand up and move around at least a few times and up to as often as is reasonable on a flight, being periodically forced to stand by your row-mates is actually a feature, not a bug.

There are only four major reasons you would not choose a forward aisle in my mind. They are:

  1. If you’re picking premium cabin seats.
    Seats in first and business class cabins normally have enough leg room that while aisles are still nicer, being on the window is not a major impediment to getting up and moving around. Unless you make way more than me, you’ll mostly only be put in these seats on an upgrade, so don’t worry too much about it — you won’t get to pick your seat anyway.
  2. If you’re flying on a red-eye or first-thing-in-the-morning flight.
    First off, red-eyes are the worst value-for-money flight in the business; do not fly them if you can at all avoid it. That being said, the window seat may create a better napping setup, as it provides a wall to lean against. Plus, your sleep won’t be interrupted if one of your row-mates needs to get up. This only applies if the flight is three hours or shorter; on longer-haul flights, aisle access is more important than either of those benefits.
  3. Bulkheads and exit rows.
    The bulkhead (the row with no seats in front of it) and wide exit rows can be a godsend for anyone taller than about 6’4”, but otherwise avoid them. Part of the deal is that they move your tray table from a the back of the seat in front of you into an uncomfortable and rigid armrest divider, robbing you of a couple of inches of seat space and the ability to hang out into the aisle slightly. 
This goes double if it’s a mid-plane bulkhead on a 767 or similar, because that space that you thought was all yours becomes a de-facto waiting area for the bathroom on the other side of the wall in front of you, which means you get to spend much of your flight looking at and listening to the sound of butts (and if you’re trying to sleep, the area around the bathroom is usually brightly illuminated the whole flight). The row in front of an exit row is also a no-go, as they have limited or no recline to ensure there’s space in the case that the exit row actually needs to get used as an emergency exit. Sit a row or two back instead.
  4. Other anomalies.
    No heuristic is perfect. Some aircraft are just laid out weird, and the front-and-aisle heuristic doesn’t work for certain seats or even entire planes.3A good example here is tiny one-and-two regional jets. A one-seat row means you have both a window and an aisle! The best of both worlds! Not exactly — these craft are so damn tiny that the curvature of the plane’s body robs you of precious shoulder and leaning room. Sit on the aisle of the two-person row instead, or better yet, take a bigger plane. This can be mitigated with a quick check on SeatGuru or Airfleets for your specific aircraft, which will also tell you nice-to-know things like plug availability and location, and if the seat you’re picking randomly has limited recline. Be sure you search for the aircraft and airline together — different airlines will often configure the same aircraft in different ways.

On most major carriers, the seats I’m describing are almost always listed as economy plus or similar, and reserving them comes at a premium unless you have status with the airline. This shouldn’t be an issue for you, because you have status with the airline (right?), and even if you don’t, you’re a value shopper, not a price shopper (right?). Sitting in the front of the plane is worth the 10-15% increase in cost when you have to sit there every week.

Whatever seat you select at the time of booking, double-check the seatmap again at the time of check-in and look for better options. Some primo seats are artificially reserved until close to check-in time, and others will open up as the highest-status people who originally booked into them get upgraded into first.

Ticketing Carriers and Operating Carriers

Not all tickets are created equal, because the travel industry is …weird. Spend a couple of extra minutes before you book to double check two things: the operating carrier and the ticketing carrier. They will ideally match.

The operating carrier — carrier is just airline-industry speak for airline — is the business that will actually be flying your plane. It may not be the same as the ticketing carrier who you sold you the ticket. For most US travel, having a different operating carrier will be a result of regional feeder airlines, networks of smaller technically-independent partner airlines that fly short- and medium-haul flights to secondary markets like Madison, Tulsa, St. Petersburg and Cincinnati.

Look for something like “OPERATED BY: WESTJET AIRLINES DBA UNITED EXPRESS,” directly below the main flight details on whatever booking site you’re using; this may require to open an expandable “more information” drawer.

I try to stay away from regional carriers. I’ve heard stories about some of these regional carriers having lower aircraft maintenance standards or lower-quality flight attendants and in-flight service, so that may be a concern, but I’ve honestly never noticed much of a difference. I personally stay away because they fly old and small planes, which leads to gate-checked bags, uncomfortable seating, and bumpy flights. Often these planes are hand-me-down regional jets that were purchased second-hand from larger carriers after a fleet upgrade, and as such are often worse than flying an RJ on a major carrier, which is already not a pleasant experience.

In the case of regional feeders, your tickets are still on the main carrier’s system, you use the main carrier’s gates, and so-on. There’s really not much that will be different outside of the flight and aircraft itself.

Cross-carrier issues are trickier, and have to do with code-sharing and interlining, generally beneficial practices that can occasionally leave you in a serious lurch.

In this situation, you’re dealing with a different airline entirely. Interlining and code-sharing work by allowing you to buy tickets through one airline for flights that actually occur on a different airline, which lets carriers offer more routes to more places. Most of the time you’ll see this on multi-leg international flights, but it’s also possible to accidentally book direct domestic cross-carrier flights, especially across Star Alliance or OneWorld partners.

You buy, for example, a United Airlines ticket from Houston to Toronto. The first leg is a United flight from Houston to Chicago, on United metal, with United crew, but the Chicago to Toronto leg is actually an Air Canada flight, complete with Air Canada aircraft, gates and staff, despite being issued as a United ticket (this is interlining; selling tickets on a partner airline using your ticketing system) and potentially also a United flight code for that flight (this is code-sharing; effectively aliasing a flight as two different flights on two different carriers. It’s what allows interlining from a technical perspective).

The problems arise when you need to change basically anything about that Air Canada flight — because it’s often not clear who is allowed to make a change or rebook you, neither carrier wants to, and you have to spend three fucking hours at Chicago O’Hare walking between the United ticket counter and the Air Canada one and finally convincing an employee of one to hand-write you a note and have them call the other, and still ultimately pay a change fee for something that should have been free and taken six minutes. No, I’m not bitter.

ANYWAY, cross-carrier flights are also bad for status reasons. They make it hard-to-impossible to take advantage of a carrier’s status amenities, like a lounge or upgrade (either via voucher or status). Because you’re technically on an AC flight, you won’t be able to use an upgrade voucher and will be put in the standard upgrade queue as a Star Alliance partner, behind anyone who has comparable status on Air Canada itself. In this specific example, Star Alliance reciprocity agreements will get you in whichever lounge you prefer to be in, but that’s not always the case.

Avoid these kinds of cross-carrier flights if at all possible, and if you can’t, don’t count on the same ease of flight changes, upgrades, lounge access and other status amenities you’ve come to expect.

Fare Codes

One last thing to look at before you actually press “purchase:” what is the fare code of your ticket?

While we think about classes of service in large buckets—First, Business, Economy—airlines think of think of them in much more granular terms, designated by one-letter codes: there are often 3-5 fare codes for business and first class seats, and as many as 12-15 for economy, plus some special wildcard fare codes for things like military personnel traveling on orders. A fare code is best thought of as your real class of service. In fact, within the airline industry and on frequent flier websites, “class of service” normally refers to a specific fare code, not an entire “travel cabin” like Business.

The reasoning behind all of these different buckets comes down to price discrimination — by offering much smaller pools of tickets at different prices, the airlines can target different customer segments.

The simplest way to charge more or less for a seat within the same cabin is by changing the things that come with it. This is where you get concepts like economy plus and the unpleasant but increasingly popular economy basic, AKA economy minus, but also certain fare codes that can increase or decrease your ability to be upgraded, your ability to get the ticket refunded, and your ability to accrue status-qualifying miles.

Within a block of economy tickets with the same amenities, there might still be several different fare codes, each with different prices. The logic here is that leisure travelers, who are more price-sensitive but also more time-flexible, plan further ahead and will buy the tickets from the lower-priced buckets, leaving only the higher-priced tickets for business travelers, who often book later and don’t mind paying a little more for exactly what they want.

As such, for any economy ticket on an airline, there are always a couple of codes to prefer, and a couple to avoid. Naturally, fare codes are not standard across airlines. That would make too much sense. I’m going to use United and American as examples, but you’ll have to learn the fare codes for your airline if it’s not one of these two.

  • Prefer
    “Full-Fare Economy” codes, which are fully refundable, sometimes accrue qualifying miles at a rate of 150% or even 200% of actual mileage, and come with a high likelihood or even a guarantee for upgrades into the business class cabin if there’s space. These are codes Y and B on both United and American, and also some—but not all—W codes on American.
  • Avoid:
    “Deep Discount Economy” and “Basic Economy” codes, which are non-refundable and often non-changeable, come with no likelihood of upgrade, often restrict other benefits like seat selection, and accrue 0% to 50% of the miles. United’s are Z, P, S, T, K, L, G and N, American’s are G, N, S, Q, O and B. At the end of the day, this is another place where the minor benefit of having a higher likelihood of upgrade or the marginal cost does not outweigh more important considerations like the timing of a flight or the aircraft it’s on. Unless you’re actively gunning for a status level, or need a refundable flight, choose the flight first, and then try and get the best fare code you can.

Fly happy

All of this is easier said than done. Shopping on value and not price is strangely hard for a lot of people, myself included, because of some basic ways our brains work. We have a hard time imagining ourselves in the future, and so we book 6AM flights with long layovers on bad carriers with worse aircraft, and when we start looking at flights that aren’t the absolute cheapest, loss aversion kicks in hard — TWO HUNDRED WHOLE DOLLARS? NO WAY! I’D RATHER BE MISERABLE!

Now you is fine with future you being miserable, sure, but future you won’t like it very much. Be nice to future you: decide ahead of time what your comfort is worth. By doing this, you build it value shopping into your decision-making process ahead of time, and there’s no hemming and hawing over which flight to choose. Again, my personal rule is that per round trip, it’s worth up to $150 plus $25 per hour of additional travel time saved to buy the best flight available. Your number maybe be a little higher or lower, but pick one and stick with it.

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