How to Book a Cheap Flight

Bordeaux to Amsterdam, 2022

This isn’t where I tell you to put your rent on your credit card so you can earn points and book business class tickets for free. I’m not The Points Guy. I am, however, a savant at finding the cheapest airfare anywhere and I’m about to let you in on all my secrets one simple tip: Google Flights. Yes, it’s that easy.

Some people swear by Kayak or SkyScanner for finding flights like I’ve outlined below. Others live and die by Going (formerly Scott’s Cheap Flights) and SecretFlying for hot tips on crazy deals and airline pricing glitches. I like to monitor the last two for good deals, but the bulk of my flight-searching efforts are spent on Google Flights.

Hot Tip: While searching on Google Flights is entirely possible on your phone, I like to use a desktop to browse. Maybe it’s the #eldermillenial in me, but I like to see everything bigger.

When You Know Your Plans

You know where you’re flying from, where you’re flying into and you’ve got your dates locked down. This is the most challenging of all the scenarios, but it pays off when you’re flexible with airports and creative when it comes to to piecing together an itinerary.

Let’s look at a Thanksgiving trip to Europe to see the Christmas Markets. This is one of my favorite times to visit Europe from the US since flights are cheap and everywhere is decorated nicely for the holidays.

First, you’re going to want to search as one-ways to maximize all the possible routes coming and going. This is where I can see if there is a particular route or airline that’s majorly on sale (usually Iberia or Level to Barcelona), and either book as a open-jaw (flying into one city and leaving from another; like Boston to Barcelona, then Paris to Boston) or a roundtrip depending on price and/or flight times.

I’m based in Boston, but I can easily fly out of Boston, Providence, Manchester, Worcester, and even Hartford if the times are right. So, I’ll select Boston as my “from” and then click the + sign to add the rest of the airports. Keep the destination city blank and then select your dates. In this scenario, I’ll select the Friday before Thanksgiving.

Basel and Strasbourg are the most convenient for the Christmas Markets I’m interested in, but those one-way prices aren’t giving me good vibes. Paris for $283 isn’t bad, but I have a sneaky suspicion that’s on PLAY airlines via Reykjavik, which is super bare bones and not my first choice to get to Europe. So I’ll select the Stops: Non-stop filter to find a better-for-me option.

I had to zoom out since I needed more options, bringing in London non-stop for $348. Not only is that a great one-way price for the holidays, London is also very picturesque during Christmas and it’s a cheap & easy EasyJet or RyanAir flight from London to the Alsace.

That $371 flight to Zurich is also workable since it’s only one-stop and on IcelandAir, which is better than PLAY.

Knowing the cheaper cities to fly into, those should guide your return flights, so I’ll start looking out of Paris, London and Barcelona for the Saturday or Sunday after Thanksgiving. Here’s a non-stop from Barcelona to Boston for $305.

Coupled with the $371 to Zurich plus a quick $15 (!!!) flight from Basel to Barcelona the day before, I’m all in for $691 roundtrip. The trick with Europe is you just need to get there; once you’re there, it’s easy and cheap to get around via planes or trains. So even if you’re trying to get to Zurich, it probably will be cheaper to fly into Paris or Barcelona and then onto Zurich.

When You Have a Time Frame in Mind

You know you want to escape for a four-day weekend sometime next month. With Boston as my departure airport, I’m clicking into the date box, selecting ‘Flexible dates,’ ‘weekend trip,’ and ‘July.’

I’m also going to select Non-Stop flights and set my max budget to $500. Looks like I’m going to Aruba for $412:

When You Know Your Destination

You know where you’re going, but are open to going at different times throughout the year. For example, let’s say I need to get to Panama for a long weekend to hit 50 Before 50, but I’m not picky about the time of year I go. Knowing there are non-stop flights from Boston to Panama City, I’ll select the Stops filter and leave the dates open. I’ll then scroll through the calendar view looking for the green prices to know I’m getting the best deal, which happens to be $442 roundtrip in August or September:

Note the bottom of that screenshot above; you can adjust the timeframe to any amount of days you’re looking for.

When You’re Totally Game for Anything

Life has handed you a wide-open calendar and you’re about to set out on the trip of a lifetime. Why don’t you try booking a round-the-world trip for only $852?

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