Last Updated: 9/28/22 | September 28th, 2022
Booking a flight can be one of the most stressful parts of travel! Airfare is expensive and, with variation in prices, we often worry that if we buy right now, prices could drop and we’d be the person who paid the most money for the flight. “Maybe if I wait just a little longer, prices will drop,” we say to ourselves.
I used to spend hours upon hours searching for the right price. I’d search multiple websites, second-guess myself, and worry about what happens when the prices drop. I would hold off on buying, waiting for that perfect moment. It was like trying to time the market — it simply doesn’t work. 99 times out of 100, you lose.
On a recent trip from Austin, a one-way ticket on American Airlines was $206 USD. The next day it was $149 USD and a BETTER route. When I checked a few hours later, it was back to $206 USD.
You can’t predict prices. The best day to book is usually today.
A while back, I went to visit the folks at Google Flights. Over lunch, they told me about a study they did on thousands of flights. They found the average drop price is about $50 USD. That means if you wait, you’re most likely to save about $50 USD but might be stuck with a price that is hundreds higher. (This excludes sales and mistake fares.)
As someone who doesn’t go a day without searching for airfare to regions all over the world, I can tell you that you can’t second-guess yourself. If you’re comfortable with the price you paid, you need to accept it and move on — even if airfare drops.
In the past, I’ve explained how to find a cheap flight and the theory and strategy to use when searching for a flight. Today, I want to show you how to put that into practice and walk you through how I book my tickets.
After that, I start with the ITA Matrix, an amazing tool that allows for complex searching and that every flight junkie I know uses. While it only searches major airlines (no budget carriers here), it has a calendar option so you can see prices over the course of the month and provides a solid baseline on prices.
Being flexible with your dates is key to booking cheap airfare, so getting an overview of an entire month is important. In fact, being flexible with your destination can yield even cheaper fares. If you aren’t set on somewhere in particular, use the “everywhere” option in flight search engines like Skyscanner or Google Flights and see what you can find.
But for the purposes of this article, I’m going to use concrete destinations. Let’s look at our example route from New York to Barcelona:
You can see at a glance that the cheapest flight for this route is $425 USD. But click through to choose your dates and booking options, and you’ll get the full picture:
As you can see, although the cheapest round-trip flight is indeed $425 USD, this TAP Portugal flight has a layover in Lisbon and returns to a different airport than you left from (leaving JFK, returning to EWR). For just $490 USD round-trip, you can fly direct with American or Finnair, leaving from and returning to JFK, a much better flight overall.
New York to Barcelona on Skyscanner:
Skyscanner brought up flights with budget airlines LEVEL and Vueling. While the price differential isn’t huge ($474 USD on budget airlines vs $490 USD on major carriers), you can see that Skyscanner brings up different flights and results, making it worth checking.
New York to Barcelona on Momondo:
You’ll also notice Momondo brought up the cheapest flight of all, for $333 USD round-trip. If you look at the details though, it has an incredibly long layover in Lisbon, so probably not worth booking. Still, that’s another reason to check multiple booking sites. You might find a cheaper price elsewhere!
Next, I visit Google Flights to search regional fares. For example, if I’m flying to Barcelona, I’ll see what flights to nearby airports might be cheaper. It may be cheaper to fly into London, a major hub, and take a budget airline to Barcelona.
Though you’ll end up booking two different tickets on two different airlines, you can sometimes save hundreds of dollars. I once booked a flight to Dublin and then flew Ryanair to Paris, saving me $200 USD instead of taking a direct flight.
In Europe, there are plenty of options for doing this, since there are a lot of airports and budget carriers to choose from.
If you aren’t a junkie like me and know which budget airlines fly where, visit the airport’s website to get a list of airlines.
Or, simply put your departure airport into Google Flights and a larger region as the arrival airport. In this case, you can put in “Europe,” which will bring up a map view of the cheapest flights from New York to anywhere in Europe:
I see that leaving on the 17th there’s a $376 USD flight to Lisbon, one of the cheapest options for getting from New York to Europe. I then do a separate search for flights on those dates from Lisbon to Barcelona. I discover that it’s only a $57 USD round-trip flight on Ryanair, bringing the grand total to $433 USD round-trip.
This saves $16-57 USD (depending on if you go with a budget airline like LEVEL or major carrier like American), but when you factor in immigration, checking into a new airline, possible delays, and your time, it’s not worth it. This doesn’t produce anything cheaper without extremely long layovers.
I don’t believe saving $57 USD is worth an extra 20 hours in an airport. Though I have used this method to save money in the past, in this case, booking two separate flights isn’t worth it so I move on.
Even if the savings seems pretty decent, you’ll still want to watch out for budget airlines’ notorious fees, because they could negate any possible savings. These airlines usually charge fees for checked bags, carry-on luggage, printing your boarding pass, using a credit card, and anything else they can get away with. Be sure to add up the cost of the ticket AND the fees to make sure that the price is lower than a larger carrier.
I usually only use this method if it will save me more than $150 USD, and if there are at least 3 hours between connections. Since you’re booking two separate tickets, if there are delays on your first leg that cause you to miss your second flight, the airline isn’t responsible for rebooking you.
After looking at these three websites, I’ll visit the airlines’ websites to see if there are any cheaper deals to be found. In order to encourage consumers to book directly with them, airlines often have cheaper prices listed on their websites.
In this flight example, the airlines’ websites were offering the same or more expensive fares, as you can see with this American Airlines flight (that ITA Matrix found for $490):
This isn’t always the case though, and sometimes you can find cheaper fares when booking directly. A quick search of airline websites will ensure that you’ve exhausted all your options.
After booking the flight, I make a note to check back in 23 hours as you have 24 hours to cancel a flight without penalty. Right before that time is up, I’ll do a quick search to see if the price dropped (see my Austin example above). I’ll either rebook or keep my flight based on what I find.
After that, I don’t give it a second thought, even if two weeks later there’s a sale or I see cheaper prices pop up somewhere. You can’t know the future or when a sale will come. You can only make your best decision with the information at hand at the very moment you’re booking.
Maybe you’ll spend 10 hours searching to find some obscure website that is $5 USD cheaper. Maybe your flight will become $200 USD cheaper the next day. Maybe there will be a sale. Maybe the price will go up!
In the end, it is not worth worrying about.
First, you’ll be frozen with potential buyer’s remorse if you worry about future prices. You’ll never buy a flight because you’ll always be wondering “what if?” In the end, you’ll wait too long — and probably pay more. Second, how much is your time worth? Maybe I could search more, but I’d rather use those extra hours to enjoy life, plan a trip, work on my blog, or relax at the beach. My time is more valuable than a slight drop in price will ever be.
If you’re spending more than an hour booking a flight, you’re spending too much time. This entire process from start to finish took me 40 minutes. After that, I went back to watching Narcos on Netflix. I never second-guess myself on flights. You’ll go crazy if you do. Spend 30-40 minutes finding a cheap flight at a price you’re OK paying (Still too much money after all of this? Go somewhere else), book it, and move on with your life.
Book Your Trip: Logistical Tips and Tricks
Book Your Flight
Find a cheap flight by using Skyscanner. It’s my favorite search engine because it searches websites and airlines around the globe so you always know no stone is being left unturned.
Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and hotels.
Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:
- SafetyWing (best for everyone)
- Insure My Trip (for those 70 and over)
- Medjet (for additional evacuation coverage)
Want to Travel for Free?
Travel credit cards allow you to earn points that can be redeemed for free flights and accommodation — all without any extra spending. Check out my guide to picking the right card and my current favorites to get started and see the latest best deals.
Need Help Finding Activities for Your Trip?
Get Your Guide is a huge online marketplace where you can find cool walking tours, fun excursions, skip-the-line tickets, private guides, and more.
Ready to Book Your Trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use when I travel. They are the best in class and you can’t go wrong using them on your trip.