Travel Tips & Tricks

A Guide To Finding The Right Flight Every Single Time

October 27, 2018

For any trip that involves flying somewhere, your flight is the starting point of the trip. Until you know which arrival and departure times are available on which dates, and if they fit in your budget, you can’t get your housing or begin building out an epic itinerary.

This is part of a series on how to plan epic trips. Here are the other detailed posts on trip planning, and you can also download my free e-book for dozens more trip planning tips on flights, housing, itinerary, and more!

Getting Started Planning A Trip: Important Questions To Guide You

My Trip Planning Process: Inspiration, Research, Realism

How to Pick the Perfect Hotel or Rental Every Single Time

How to Put Together Epic (& Feasible) Itineraries

There are so many tools, websites, and tips out there for booking flights that it can feel overwhelming, even for someone who travels a ton.

So over the years I’ve developed a simple but super effective process for how to find the best flights for any kind of trip, and I decided to outline my entire process to help others who feel overwhelmed by the choices.

What this post covers:

What do I mean by “right” flight?
Searching from an Incognito browser
Where to search for the best flights flights
How to accurately compare different flights
Picking a seat you’ll enjoy
Is it time to pull the trigger??

Wait, what do you mean “right” flight??

First, let’s level-set on expectations here. I said “right” flight in the title because when it comes to how to find the best flights, it’s the key word to keep in mind. Sometimes that’s the absolute cheapest, but for most of us we also have to balance the cost with how much time it takes.

For instance, if a non-stop flight to London from Atlanta is $1,000 but I can get a flight with two layovers and a total travel time of 23 hours for $800, I’m going to pay the extra $200 and fly non-stop.

My time is worth money, so that’s what’s right for me. That isn’t always the case, and it doesn’t mean it’s right for everyone. You know what balance of cost and time is most important for you. These tips can be applied no matter what.

You might also like: 15+ Of The Best Tips For Avoiding (& Surviving) Air Travel Woes

To start: search under the radar

First tip: always use an Incognito browser! I use Chrome exclusively, and they’ve taken away the easiest way to get to Incognito, but it’s still totally possible. Now what you have to do when you’re in Chrome is hit “CTRL + Shift + N”. There is a slightly different process depending on whether you’re a Mac or Windows user and your preferred browser, but a quick Google search should get you sorted out.

Ultimately this means that the browser doesn’t have your past browsing history, so the airline sites can’t increase prices just because they know you’ve been looking for a particular flight.

BUT, unlike “Guest Mode” (also a choice), the browser remembers your saved passwords and such—super helpful if you’re ready to actually book your flight and need to sign into your airline miles account, for instance.

Mozilla has a similar offering, and I’m assuming Internet Explorer does too. If you want to know more about Incognito and Guest modes in Chrome, this link is helpful.

You might also like: 11 of My Best Travel Tips for ANY Trip

Where to search for flights

I recommend that any time you’re looking for a flight (particularly an international flight), you search on at least four search engines to see what differences there are. Sometimes they’re negligible, but other times you’ll be surprised.
- Kayak, Google Flights, Momondo, and Skyscanner are the ones I use currently. One helpful thing about Google Flights is that it also pulls in results from a lot of the smaller budget airlines, especially internationally. In fact, I’ve been using Google Flights super heavily lately, with the others as only supplemental.
- I have not found Expedia, Travelocity, or Orbitz to be particularly useful (and I feel like they’re mostly owned by the same people); I freely admit I have no idea how to use Hotwire or Priceline and honestly, they stress me out when I try to.
I also recommend signing up for some of the flight sale notification websites. AllTheFlightDeals.com, NextVacay, and Scott’s Cheap Flights are three I’ve used, and most of these sites have both free and paid versions.
- On these sites you enter your home airport (as well as other airports you’re willing to fly out of if there’s a great deal) and they’ll send you emails when good flights appear. It might be to San Diego or to Nairobi, but keep an eye out and you’ll probably see what you’re looking for eventually.
- Try all three (and any others you find) with the free versions, which will give you a sense of which is the best fit for your home airports and the types of destinations you’re looking for, and then consider trying out the paid version (it’s typically pretty affordable and one cheap flight will more than pay for it).
If you collect frequent flyer miles either through an airline program or a credit card (like Chase Rewards), make sure to check your balances to see if you have enough miles to cash in.
- For instance, I decided to cash in like 150,000 Delta miles for a business/first (Delta One) flight to London last year, and it was AMAZING.
- The airlines and programs devalue miles constantly, so don’t just sit and hoard points. Use them!

You might also like: Travel FAQ: How To Pay For Things While Traveling

How to compare flights

I believe there’s an art to how to compare flights, and it’s key in how to find the best flights. Price is where most people automatically gravitate, and it’s certainly important. But price depends on a number of different factors, and you need to look at all of them when picking a flight.

Some things are really obvious—for instance, dates and time of departure and arrival. If you can be flexible on dates and times, you have a good chance of getting a better deal. But outside of those, many people don’t think about some of the other important factors. I’ve outlined a few here, and there’s a helpful diagram below to show how you find some of these elements on a flight search listing.

Airline

Airline is one thing that can make a huge difference in your overall trip experience. Make sure you understand whether you’re booking a low-cost carrier (such as Frontier, Spirit, or Norwegian). There’s nothing wrong with it, but the fees can add up so you should go in eyes-wide.

Look up reviews of different foreign airlines and ask friends as well—some are amazing (Turkish, for instance) and others are a little more bare-bones (looking at you, TAP Portugal).

Pro tip: Make sure to look not only at what airline you’re booking with, but what carrier is actually servicing the flight. Due to alliances, this is often unclear and really makes a difference in your experience.

Total travel time

Total travel time is one of my hot buttons when booking a flight. Long layovers waste your valuable time unless they’re SO long that you can actually get out of the airport and see a bit of your layover city (inherent with its own luggage logistical issues).

Too short can be a concern too, though at least if you’re booked all the way with one airline they’ll have to make it work for you somehow. Just make sure to check not only the number of layovers but your overall travel time before booking.

Destination airport

This sounds like a no-brainer but you’d be surprised how often it trips people up—make sure to check the airport you’re flying in and out of.

You can sometimes nab a better deal by using a different nearby airport, but sometimes you don’t realize that you’re booking London Gatwick rather than London Heathrow and will have a super long train or expensive cab ride to get into the city.

And if you’re flying to NYC, there are major pros and cons to all three NYC airports, so ask around. Again, eyes-wide. As long as you make the choice on purpose, that’s what matters.

Choosing a seat you’ll enjoy

For international flights, most airlines (except budget ones) let you pick your seats when you book. So make sure to decide whether you want a window or an aisle (or…middle, I guess? But why?). I generally go for window, since it’s easier to sleep without people walking past constantly. The downside to that is that it’s harder to get out if you want to stretch or go to the bathroom.

If you’re traveling with companions and you’re all booking your flights together, I recommend booking at the same time and talking on the phone to make sure you choose seats together (if you care).

Here’s a tip for you if it’s a 3-seat window and aisle (like on many domestic flights)—if two of you are traveling together, you can grab the window and the aisle with the middle empty between you.

Others choosing their seats will be less likely to choose a middle seat unless they have to, so you might get lucky and have an empty seat. And if you do end up with someone between you, a middle seat person will ALWAYS swap you for a window or aisle!

Make sure to check whether you’re right next to a bathroom. Most bulkheads—a.k.a. the seats with a wall in front of them and more leg room—are by the bathroom, so that’s a trade-off, but particularly near the back of the plane that tends to be a high-traffic, high-sound, sometimes high-smell area. I usually avoid it.

I try to be closer to the front of the aircraft so I can de-plane sooner and get through customs more quickly. It can make a 30-minute or more difference in getting to your final destination.

One last critical thing to know

Here’s something that the airlines don’t talk about a ton, but has been a GAMECHANGER for me. Most airlines have a 24-hour cancellation policy—even non-refundable ones. Key word is most.

In some cases it’s a cancellation policy, in others they allow you to hold the ticket without payment up to 24 hours. But major U.S. airlines by DOT regulations have to allow this, and I’ve seen the same with European airlines (who tend to have much better customer service policies in general).

You can read more about the ins and outs of the policy here, and the most critical thing is to read the fine print on every ticket if you think there’s a chance you’d want to cancel. This only burned me once, and it was when I was booking on a random 3rd-party cheap flights site I’d never heard of, and they had a complete no-cancel policy.

But if you find a great flight and are still trying to lock down a few details with travel companions (or time off work), it’s worth reading the fine print of the airline’s policy and possibly grabbing the flight, then using your 24 hours to confirm.

@farewhispers and I have done this a million times to grab a sale fare, then work out our travel plans, and in a few cases have released the flights just because it didn’t quite work out.

And there you have it! How to find the best flights, and the detailed process I use each time I book—where I search, what I look at on the listings, and how I find the right flight for me every time.

I’d love to hear from you with any questions in the comments, or let me know if you have some other great tips that should be included here!

Other resources for epic trip planning:

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