The Art of Finding Cheap Flights in 2020

Having flown over 300,000 miles in the past 2 years, I learned that even the smallest savings add up. Especially when you spend a little extra effort booking flights. My name is Doug Ward and I run a small business relocating animals across the globe for military members, families, and shelters. I end up booking a lot of flights across the globe out of my own pocket and have learned a great deal about the airline industry in the process. Throughout this article I will break down the method you should use to purchase any flight. There are four steps to become familiar with before you get out there and find that perfect flight: How to Fly, When to Fly, When to Book, and How to Book. It may seem elementary, but there is a lot to consider when booking your ticket.

Now before we get started, let’s cover the first rule of finding cheap flights. When most people search for flights, it starts and ends with one booking engine. This ends up costing them a lot of extra money. Instead, take the time to really search for flights using the three sites I have listed below (Kiwi, Skiplagged, Google Flights); if you can do this, you’re already miles ahead of the average joe. The bottom line is if you’re willing to put the time and effort into looking for the cheapest flights, it will pay off.

How to Fly

Whether you have United Elite Status or just fly a few times a year, following these three guidelines will better prepare you to fly on a budget.

  1. “Carry On Only”: Sometimes it is possible to take something bigger — like a 35L backpack — as a personal item. (It doesn’t fit within the “personal item” size but since it’s on your back, airlines won’t hassle you. Source: I’ve done it on over 40 flights across the globe)
  2. “Budget or Bust” : No complimentary drinks/food or extra legroom on your flights at these prices. Make sure to bring lots of snacks!
  3. “Don’t Worry” : The following advice will cause more stress when flying and/or booking. If you find stress extremely bothersome, you may want to avoid some of these recommendations.

If this style of travel sounds doable, you should be able to follow most of the advice to come.

When to Fly

Airlines are priced based on demand. Before you start planning your epic vacation, consider how many other people are looking to travel during the same time. More People Traveling= Higher Prices.

  • Be Flexible: Being able to move your travel dates +/- 3 days will allow for more options and a higher possibility of cheaper tickets.
  • No Weekend Trips: If your job/life allows travel on Tuesdays, Wednesdays, and Saturdays, you’re in luck! These are the generally the lowest demand days. Weekend trips — Friday through Sunday — are the one of the most expensive travel choices.
  • Don’t Travel on School Breaks or Holidays: School breaks are the most expensive times to travel and it’s no question why: Demand is extremely high. Everyone is trying to go home for the holidays or travel to some far off place. You can expect to pay as high as 400% more than you would during a low demand time.

When to Book

Now that you know when to travel, let’s jump into when to book your flights. Deciding when to book is one of the hardest and most speculative parts of budget travel. There is no perfect formula on when to book the cheapest airline ticket, but there are a few trends to follow to make sure you’re not overpaying.

  • $$$-$$$$ Extreme Planners (6 Months — 1 Year): If you’re someone who plans vacations a year in advance, you will NEVER find a good deal. Airlines charge inflated prices this far ahead.
  • $$$-$$$$ Last Minute (Less than 7 Days): Airlines notoriously increase flight prices starting about two weeks ahead of time for high demand days, and one week ahead for low demand days.
  • $$-$$$ Regular People (1 Months — 6 Months): Most people currently fall into this category. People like to plan for the near future and can get a range of prices in this time frame. Generally not the best time to book but there are still deals to be found.
  • $-$$ Deal Hunters ( 1 1/2 Weeks — 3 Months): This is generally the best time to buy flights. You’re not booking last minute and you’re not planning too far ahead; At this point, airlines are still teasing out demand and have plenty of seats to fill.

Pro Tip: One of the best ways to find deals in this time frame is to sign up for your local budget airliners email campaigns. Wait for the deals and keep looking! If your route isn’t on sale, look for other deals. Make sure to sign up with an email you check relatively often and will at least skim the subject lines budget airliners often run short term deals such as 90% OFF, $15 Flights and more. Most of these have heavy restrictions on dates and days of the week here is an example of Frontier’s 90% OFF Deal that runs almost once a week:
- Must book in the next 48hrs
- Valid for domestic nonstop travel on Tuesday, Wednesdays, and Saturdays
- Within the next 2 months
- Not valid on Holiday weeks (Nov 17–27)
- Applies to fare only, not taxes or fees

Sign up for Budget Airline Email Newsletters below:

- USA
Frontier Airlines
Spirit Airlines
- US International
WOW
Norwegian
TAP Portugal
- Europe
Ryan Air
Wizz Air
EasyJet

How to Book

Now for the fun part, shopping around for the best flights! Once you know where and when you want to travel check these all three of these magic-powered travel sites:

1. Kiwi.com:

Magic Power:🌩 Kiwi allows for multiple one-way flights to be connected that would otherwise not be booked together.

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Kiwi is the best booking engine for budget travel because it searches through all flights that could possibly be connected and gives you multiple options. For example, if you’re flying one way from New York to Alicante most flights would cost around $500 on your average booking engine. Kiwi will find unique connections between airlines, like flying Norwegian Air to Dublin, then RyanAir the rest of the way to Alicante for $160. These flights would never be paired on Google Flights, Kayak or any similar booking engine. In this way, Kiwi helps users to find more affordable, time efficient flights and offers more options to choose from. Kiwi also allows users to choose flexible date ranges and alternative airports that may have cheaper flights. You can often save hundreds of dollars by flying to an airport that is only a 30min drive away, or moving your vacation +/- three days. One of the greatest advantages of booking with Kiwi is that they guarantee your whole itinerary even when you book with multiple airlines.

Pro Tip: Email me if you want $23 off your first flight of $200 or more! (me@dougward.xyz)

2. Skiplagged.com :

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Magic Power🌩: Skiplagged allows you to book flights where you can get off on a layover stop.

Skiplagged is a hidden gem for booking flights. For example, you’re traveling from Anchorage to Denver. You can book a flight from Anchorage to Los Angeles and get off the plane on your stopover in Denver, saving time and money. There are a few caveats with this kind of travel. First, Airlines don’t like it, although it is not illegal or punishable. Second, you cannot check any bags. Your bags would end up in Los Angeles. Third, you cannot get airline miles for the travel and should not associate your frequent flier numbers with these flights. This is because you will not be flying the last leg of your booking, and the airline could possibly blacklist your airline mileage account. Despite the drawbacks, who wouldn’t want to save 7 hours of travel and $81?

Google Flights:

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Multi-City Trip Example

Magic Power🌩: Google Flights is the best way to check that your getting the best deal from the previous sites.

Google Flights lets you to take advantage of the speed and power of google when looking for flights. It allows you to easily view the regularly connecting flights and compare your results with the past two sites. It is also one of the best sites to use when booking a Multi-City trip, providing fast results when you want to search new dates or locations.

Pro Tip: Kiwi generally adds $10–50 to your booking when they connect flights, so search your favored Kiwi flight itinerary on Google Flights using the Multi-City feature and book them separately without Kiwi to save more.

Time to Book!

You can expect to spend at least 15 minutes searching for flights with these sites, and it will be one of the best time/money returns out there! After looking through the possibilities, you are now ready to weigh your options — from costs to travel time — and make the decision that works best for you.

Still need some help finding the perfect flight? Check out r/airfarehunting on Reddit to have someone hunt down some cheaper flights!

If you want to pick my brain about travel, talk about flight economics, Venmo me $5 to find you the perfect flight, or just say hi, you can learn more about me and how to reach me on my website!

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