How To Find The Cheapest Flight Possible

Airfare is expensive, and is often what holds many of us back from pulling the trigger on booking our next trip. This guide aims to help make the process a bit more affordable.

By: Brian Fulda

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It happens all the time. You see a photo of a gorgeous place somewhere and instantly catch the travel bug. Just for kicks, you decide you want to look up how much flights cost to go there. You're already excited about the idea of going, but to your alarm, the cost of the flight alone is way out of your budget. You sigh, close your internet browser, and shuffle the idea into the back of your brain, where it remains there, forgotten. Back to daily life at home it is.

Finding cheap airfare isn't easy. Otherwise, everyone would do it. But if you're willing to dedicate a little bit of time and put up with some daily email alerts, you can find flights well within your budget, leaving you extra money to spend on having fun once you get there. Between my good friend and I in the past year, we've flown from San Francisco to Ireland, Brazil, Hawaii, and even Indonesia, all without spending more than $500 on any of those round trip flights.

First thing's first, there are a few general tips that apply to the entire airline industry for flying on a budget:

  1. Certain days of the week are cheaper to fly than others. Tuesdays and Wednesdays are statistically the cheapest to travel, with Saturdays not far behind. Fridays and Sundays are usually the most expensive.
  2. Avoid flying close to major holidays at all costs. Airlines know you want to be with your family for holidays like Christmas, and therefore jack up the prices around these dates. The more "cushion" of days you can add before and after a holiday, the cheaper your flight will be. Adversely, flying on major holidays can actually save you a ton of money.
  3. Prices can drastically change from season to season. Since most people vacation in the summer, June and July are the most expensive months to fly (in the northern hemisphere) while January and February are usually the cheapest.
  4. The more flexibility you have, the cheaper the flight you will find. Of course, most of us work full time jobs and only get limited time off per year to travel. However, if you can find a wide open patch of time off, such as between jobs, working a seasonal job, or even utilizing a 3-day weekend to take a day or two off on either end, these can be the best times to travel.

Now that you know these tips, we can move on to the best websites, tools, and apps for finding an affordable flight. Do note that the more of these you use, the better chance you have of finding the cheapest flight.

  • The Flight Deal. When people ask me how I manage to travel so affordably, this is the first thing I tell them I use. Behind The Flight Deal is an amazing team of people that spend all day scouring the web for affordable airfare. I am signed up for The Flight Deal's daily newsletter, which gives me a list of roughly 10-20 deals per day from different airports. I also follow them on Twitter, which is the best place to see deals first. The catch with The Flight Deal is that the deals they find usually only last for a day or two at most, and can sometimes be gone in a matter of minutes, like in the case of a flash sale. However, if you have a flexible schedule, and are willing to be a little bit spontaneous, this is arguably the best site to find the cheapest flight. We're talking San Francisco to Dublin, Ireland for $410, or San Francisco to Hawaii for $180 (yes, both round-trip) cheap. If spontaneity scares you, keep in mind that as long as you've booked a ticket 7+ days ahead of your flight, you can cancel your flight for up to 24 hours after you purchased tickets. I've often jumped on a flash sale deal and then decided within the next day if I wanted to cancel or not. This applies to any flight departing from the US, but I can't speak for other countries. Unfortunately, The Flight Deal only serves a handful of major US cities right now, but that is only bound to grow in the future.
  • AirfareWatchdog. This is a similar site to The Flight Deal, but allows for a little bit more personalization. Unlike The Flight Deal, you can sign up for their e-mail newsletter to only send you deals to and/or from specific destinations. This is incredibly handy if you are only looking for a cheap flight from say, Los Angeles to Hong Kong. You can also just set it to send you deals leaving from your home airport, so you get an e-mail listing all of the deals departing from Los Angeles. Yet another option AirfareWatchdog offers is to change the frequency of e-mails between daily, a few times per week, or weekly. The Flight Deal only offers a daily e-mail option.
  • Google Flights. This might be my favorite tool for quickly and efficiently finding the most affordable flight for my specifications. With Google Flights, you can enter any two destinations, add nearby airports, and look at an actual calendar of when is cheapest to fly (best priced flights show up in green). Additionally, you can specify the number of layovers you have, a maximum price ceiling, airlines you prefer, time of day you fly, and even more, like multi-city trips. Keep in mind that the more specifics you pick, the less chances you have of finding the cheapest flights. Another unique feature about Google Flights is that it tells you some fine points about the type of aircraft you would be flying, such as how much legroom you'll have, if the flight offers WiFi, and more. (Note: Google Flights does not search for certain airlines, such as Southwest, so always make sure to check their sites to get the best deal.)
  • ITA Matrix. You've probably heard of Google Flights before reading this, but this site is like Google Flights on steroids. It's also run by Google, but what makes ITA Matrix unique is that it lets you get into nitty-gritty specifics if you need them. For example, let's say you're looking to do a backpacking trip in Europe this summer, but you're flexible on the amount of days you can spend there. You can tell ITA Matrix to find the cheapest round trip flight between, say, 8-12 days. This is very helpful if you're still deciding how long you want to spend somewhere.
  • Hopper. If you're not sure exactly what is a good deal for a certain flight, Hopper is an excellent tool to scope out what the initial cost should roughly be. While it only exists in app form, Hopper is available for both iOS and Android devices. What it does is collects data over time, taking into account things like seasonal fares, best days of the week to fly, etc, and compiles it into an extremely simple calendar showing you when is the best time to book. Unlike the other sites listed above, it is the only one in which you can actually book a flight through.
  • Skiplagged. This site made controversial news last year when United's lawsuit against it was thrown out by a judge. What Skiplagged does is finds multi-legged flights with a layover in your final destination city that are cheaper than non-stops to said city. So, let's say you want to fly from Philadelphia to San Francisco, but nonstop flights are very expensive for your dates. However, Skiplagged shows a flight from Philadelphia to Las Vegas with a layover in San Francisco for an affordable price. This exact scenario happened to me before, and I just got off my flight in San Francisco and skipped the second leg to Las Vegas. Strangely, this can sometimes save money versus flying nonstop, but if you're feeling desperate, this can be a lifesaver.
  • Expedia, Orbitz, Kayak, and many others. Everyone's heard of these flight-booking sites, but they're always good to check because they can have deals that don't show up on other sites. For example, I used Google Flights to find the cheapest airfare to Iceland not too long ago, which was on Icelandair. I had almost booked my flight on Icelandair's website when I decided to check Expedia at the last minute, and to my surprise, they had the same flight for 70 dollars cheaper! I was amazed at how the airline's site, which almost always has the most accurate prices, was actually more expensive than booking through Expedia. Also, these sites can offer special deals when you book any combination of a flight, hotel, rental car together. So just be aware that the cheapest flight can be somewhere you least expect.

Lastly, I encourage you to do even more research than what's listed above before you travel, as some airlines offer unique deals that can't be found anywhere else. For example, since Iceland is located between North America and Europe, Icelandair offers a stopover (a layover longer than 24 hours) for up to 7 days in Iceland at no additional charge on any of their flights between the two continents. 

Hopefully this guide feel a little bit less intimidated by the cost of flying and you can finally cross that once-in-a-lifetime trip off your bucket list. Good luck and safe travels!

Please respect the places you find on The Outbound.

Always practice Leave No Trace ethics on your adventures. Be aware of local regulations and don't damage these amazing places for the sake of a photograph.