The Seasoned Cynic's Guide to Cheap Flights

I started traveling in 2015. After a difficult couple of years, the answer to all my problems seemed like a poorly-planned solo trip to Italy. Lucky for me, it DID change my life for the better! The past three years have taken me all over 3 continents, and I have to be honest that I’m addicted to wandering the globe.

When I discuss my trips with others, they often tell me how jealous they are that I must have tons of money to travel as much as I do. The truth is that I have the time to travel because I’m self-employed and don’t have any children, but what’s more important is that I don’t spend very much on traveling because you don’t have to be rich to take vacations. The main expense is the flights, and there are many tricks you can use to lower (or even eliminate) the costs. Once the plane is taken care of, what you spend during your trip doesn’t have to be any more expensive than your daily cost of living at home. In fact, there are many places where you’ll spend even less - in Thailand, most of the hearty, healthy street food was about $1 for what was the equivalent of a full meal for me! Stick around and I will share everything I know about seeing the world without breaking the bank.

Here are my tips for finding an affordable flight:

  1. Use! It is an amazing resource for finding and comparing cheap flights. You can find roundtrip airfare to Europe for $400 or less. If you ask it to, it will even track prices and alert you to changes for the worse or for the better so that you can find the perfect way to reach your destination. Just don’t tell anybody about the site. Shh.

  2. When searching, use sites that allow you to look at an entire month of prices so you can see and select the best day to fly out. My favorites are Skyscanner and Google Flights.

  3. Book as soon as you can, but be aware that the optimal time to book a flight is 6-8 weeks from when you want to fly. If you are wanting to go somewhere during a peak season (ie. Paris during the summer), you’ll want to book 3 months out. Keep in mind, though, that going to popular destinations during the summer or right before major holidays will be expensive, so these aren’t the times to be relying on finding cheap airfare.

  4. As hinted at in #3, visit places off season! Don’t go to Rome during the summer time and don't go to Hawaii for Christmas. If you can, you always want to skip times of the year when most people will be traveling because their kids are out of school. To save money, travel during late autumn and winter. PRO TIP: go to places that are cold during winter (Canada, Germany, Norway, Denmark, Sweden…) because they have been dealing with crazy cold winters for a long time and know how to ROCK them! You can often experience countries at their most authentic when you go at times there aren’t many tourists. Most people want to run away to an island when it’s cold at home, you know? Therefore tickets to warm places will be pricey. You can save a bundle by going someplace most people wouldn’t think to go at particular times of the year. Might be a bit chilly, but a hot, boozy mug of Gløgg in Copenhagen will warm the tips of your toes.

  5. Choose flights that are in the middle of the week, on the day of a major holiday, on the day after a major holiday, late at night, or very early in the morning. Less people want these flights or are able to take them.

  6. Go to discount sites that post tickets that are on sale because of various errors! Check out Secret Flying and Airfare Watchdog. You can also find deals sometimes by directly searching flights on the website of a particular airline you like.

  7. Book your own connecting flight! Get a ticket to fly into a location between your home and your final destination, then grab a cheap ticket to your destination that leaves more than 3 hours after your first flight lands - that way, you’re safe if the initial flight comes in late. You can often save hundreds of dollars by doing this, and you can even plan to have that first flight land in a place you want to visit so that you get to spend a few days there before hopping onto your second flight! Airwander is good for this and will even allow multiple destinations before you get to the final one.

  8. Use a budget airline! I have seen roundtrip flights to Europe for $250 or $300. These tickets are totally worth it if you can deal with a loss of leg room, free snacks, etc. Do keep in mind that these airlines make money from charging for things such as getting your boarding passes printed and beverages. You are certainly able to see everything that you will get charged for, and you want to total up the fees to make sure they don’t result in a ticket that’s just as expensive as one from a regular airline.

  9. If you are a student, look for student discounts! You can save quite a lot by simply seeking or requesting lower rates. We’re talking like 20% more ramen in your life.

  10. ALWAYS search for a ticket as a single person. Why? Well, if you seek out a group of tickets, you will be given a price based on the most expensive ticket regardless of age, different parts of the plane, or any other factor. If you search as a single person, you can find a great deal and individually buy all of the tickets you need. Simply by doing this, you will find lower rates and pay less for your airfare.

  11. If your home currency is stronger than the currency of a potential destination, search for tickets in the foreign currency - a weaker currency can often result in the same ticket on the same airline for a lower price simply because it has less value. This doesn’t always work, but sometimes it does!

  12. Get a credit card that gives you fantastic points or miles that you can hoard and apply to travel. I own a restaurant and a product line, so I have to spend a certain amount of money anyway, therefore I am always earning points that I can apply to travel by using cards that reward me. Even if you don’t own a business, you surely have regular expenses, too, and you could be earning trips with the right cards! There are various airline rewards credit cards that help you rack up points and give you different perks like waived baggage fees. I would definitely suggest you doing a little research on which one makes the most sense for you. PRO TIP: My only specific recommendation is the Chase Sapphire Preferred card, which I personally use and love. If you spend $4000 in the first 3 months of having it, you get enough points to trade in for a $650 flight. That’s a major help if you know you’re going to be spending practical money at home AND want to take a trip! (I was not paid to tell you any of this.)

  13. For my 13th and final tip, if you start traveling, realize that it’s far more affordable than you think, and decide to start doing it regularly, pick out a large home base to fly in and out of (roundtrip) every time you visit a particular continent. My “home base” when I go to Europe is Paris. It is a major city, so there are a genuinely staggering amount of planes that enter and leave it every day. Because there are so many flights, you can score deals on tickets every day, and once you’ve been to the city a few times, you’ll experience a level of comfort that will give you some confidence, allowing you to feel energized and focused when you arrive. Scoring deals on tickets to get out of Paris is beyond easy (think a flight to Spain for like $45!!), so you can hop around the continent cheaply, then return to your tried and true Paris for a little R&R in a place you know before heading home.

Thanks for reading. Do YOU have any tips to add? Email me or start a conversation in the comments!

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