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By the way, this is just an image. You can’t really search for flights here.

As I began to consider the possibility of traveling while working, I started searching for cheap flights and Airbnbs to see if it was something that Way and I could afford.

Initially, my search led to many frustrations and that is when I changed my priorities. Instead of searching by destination, I embraced the adventuring mindset and started searching by price. I knew any destination would be a chance to revisit an old favorite or find a new one.

That led me to Puerto Vallarta, Mexico (from Tucson and back to Las Vegas) for $395 round trip … wait for it … in First Class! On top of it, it was a last minute ticket purchase because I had some family things to do that kept me stateside a bit longer than I planned. I could have gone cheaper but I wanted to kick off this adventure in style.

So here are some of the tricks I use to find cheap flights. And I say “I” because I do most of the booking, but Way helps in the searching! In fact, it didn’t take much before he also became addicted to the great cheap fare hunt.

How to Find Cheap Flights

The name of the game in cheap fare hunting is flexibility!

To find cheap flights, you need to be flexible. Most vacation planning starts with choosing a destination. But unless you have a purpose for your vacation (other than vacaying) then be flexible on the destination and maybe let the cheapest fare decide.  We chose Stresa, Italy not because of the cheap fare, (although we did find one) but because we wanted to take our youngest boy to meet his Italian family – our oldest went to meet everyone during his epic adventure following high school.

Be flexible on your departing city. Phoenix is an obvious choice for my family. I have found, however, that Phoenix is often more expensive than some other cities.  Las Vegas, Los Angeles, and even Tucson are often cheaper.

Focus on getting a cheap fare on the most expensive part of the trip and piece together the rest. Two itineraries are often cheaper than one. Always remember to check Southwest Airlines independently because their fairs do not show up in cheap fare search engines.

Be flexible on your dates. If you are traveling to Europe during the summer, chances are you will pay more than you will if you travel during September. Look for slightly off-season destinations or slightly off-peak travel times.

To find the cheapest fares avoid peak travel times such as summer (mid-June through mid-August) and major holidays and festivals in both originating and destination cities.

The bottom line is without flexibility it will be impossible to find cheap fares. There is a rarely much to be done if you are dead set on a specific destination during peak travel season from the airport closest to your home.

Favorite Cheap Fair Hunting Websites

Google Flights – I always start my search here. I can use the calendar to help me find the least expensive dates and I use the map to help me find the least expensive destinations.

Once I find a cheap fare on Google Flights, I tend to shop the itinerary around on these sites:

  • Momondo
  • Skiplagged
  • Kayak
  • Hopper (Phone App – I love searching for flights and dreaming of getting away while waiting in line. Don’t judge.)

How to Know When to Book Your Flight

I find this is the biggest challenge to finding cheap fares. Should I book or should I wait?

Oftentimes, the cheapest fares are non-refundable. That means if you book a fare and find it cheaper elsewhere you are out of luck. When I am searching for a cheap fare, I know a great deal when I see it. If it is a great deal, I book it right away. The really cheap fares don’t last long.

Fares are cheaper when purchased as round-trips. Lately, I have been booking one-ways because we want our itineraries to be flexible. It is a lot harder to find great cheap fares one-way.

Some airlines that offer one-way flights at 50% of the cost of a round-trip fare are:

Also most intra-continental budget carriers like RyanairAir Asia.

Here is a guideline (note the word “guideline”) for great round-trip fares from the U.S.:

  • Africa – $800 or below
  • Asia – $500 or below
  • Australia – $700 or below
  • Caribbean – $300 or below
  • Central America – $400 or below
  • Europe – $500 or below
  • Hawaii – $300 or below
  • South America – $600 or below

It doesn’t mean if you find a fare above these prices that they are necessarily bad. It’s just if you find fares below these prices they are exceptionally good and not likely to last.

My Approach to Booking Cheap Fares

I tend to book my fairs about three-weeks in advance unless I find a screamin’ deal. My theory (totally a guess) is that most travelers make big travel plans about a month in advance and there aren’t a lot of last-minute bookings for longer haul flights.

Here is my process:

  1. Begin searching on Google flights. I start with a general destination in mind and then explore the calendar and map for cheaper fares.
  2. Once I settle on a fare, I shop the itinerary around on the sites listed above.
  3. If I find a GREAT fare, I book it right away. Be warned GREAT cheap fares don’t last long!
  4. I set fare alerts on Google Flights, Kayak, and Hopper and evaluate the situation when I am alerted
  5. If I haven’t already, I book at three weeks out

One thing that helps me is knowing how fares fluctuate in different markets. That is why when we see a cheap fare that is GREAT, Way and I will share it. Just hit #goexplore at the top of any page to see the latest fare alerts. And then #goexplore!

One last thing, if you want a cheap fare, don’t leave it to the last minute. Cheap fares and last-minute bookings don’t play nice together. You will be more likely to find cheaper fares last minute on international flights. If you are scrambling for a cheap last-minute fare, follow the guidelines above.

Note: I don’t make any money from the links on this page – they are not affiliate links. I don’t get a commission, a royalty, or get paid to promote a fare. It’s just me sharing information with you.


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