How to Book the Cheapest Flight Possible

I can’t even count the times I’ve seen family and friends spend thousands of dollars on flights to various destinations. Most people are completely unaware of how and where to find flight deals, much less how to use points and miles to fly for free. My rule of thumb is this, if you spend over $1,000 for a flight anywhere in the world, then you paid too much. Have I paid more than $1k for a flight in the past? Absolutely, but I’ve honed my skills since then, and it won’t be happening again. Let’s run down exactly how to book the cheapest flights possible.


My favorite flight searching tool: Google Flights 

Google Flights is the easiest and most efficient flight search engine to use. All you need to do is enter a departure city and destination, as well as sample dates, and you’ll have access to the calendar view (see photo below). This is the holy grail of flight search, and the simplest way to find a cheapest fare (lowest fares in green). Make sure to view other dates because there may be sales far beyond your search dates. Just click the arrows by the calendar to tab over to other months.

Google Flights collect cookies or any of that jazz. Once you find the flight you want on Google Flights, please help support this site by using this link to Priceline to book. By using Priceline you will be given a free 24 hour cancellation policy!


How to Book the Cheapest Flight Possible

Google Flight Calendar View


Another great feature of Google Flights is the ability to use the map view known as Explore Destinations, it is located just to the right of the calendar view above. It allows you to see the prices of other destinations from your departure city. I use this very frequently when there is a sale to Europe, in order to identify other sale cities, nearby, which I might not have found yet. Another great feature is setting up a Google Price Alert to monitor price changes and book the cheapest flight possible.


How to Book the Cheapest Flight Possible

Explore Destinations Map View



Before booking your next flight always check Momondo before paying. You can usually save a few dollars by booking through one of the online travel agencies they search. Many times you won’t have the option of 24 hour cancellation and that is why it’s cheaper.

Positioning Flights

The problem with flight deals is many times they are only from select cities. Most people just ignore a mistake fare or fare deal if it’s not originating from their city. This is a huge mistake. Many times you can find a cheap round-trip fare or use points & miles to get to the city the flight deal is originating from. These are what are known as positioning flights, and they are essential to being a thrifty traveler. Just make sure to give yourself a 3-4 hour time buffer to avoid a missed flight due to a delay on your positioning flight.



Even though Google Flights generally has the cheapest airfare, there have been times when Priceline was able to find something cheaper. Do this separate from the Priceline selection within Google Flights. It’s odd but using Priceline through Google Flights and searching Priceline separate can yield different prices.



Airfarewatchdog is a great site where you can set alerts for certain departure cities and destinations and when there is a sale you will receive a notification email. I use this to let me know if there are any sales for future flights I’d like to take. It sends you a timely email with instructions on how to find the fare and you can book from there. It’s a free and a great service. Airfarewatchdog also has a listing of the top 50 fares across the United States everyday.


Thrifty Traveler Premium

Obviously we’re always keeping an eye out for the best flight deals. To get instant emails for the top flight deals we find, make sure to subscribe to Thrifty Traveler Premium. Also make sure to subscribe to our free daily newsletter, like us on Facebook, and follow us on Twitter & Instagram!


Points and Miles

If you’re willing to be flexible with your travel dates you should definitely consider utilizing points and miles to book your flights. I rarely book a trip without using points. Even 1-2 credit card sign-up bonuses should be enough for you to travel anywhere in the world. Check out our Beginner’s Guide for more details.


Bottom Line

By using the tools discussed in this article you should now know how to book the cheapest flight possible. There are so many flight deals out there everyday, but you have to be flexible and be willing to book immediately. Like I always state in my flight deals, you can cancel most fares purchased within 24 hours. Now go out there and travel smarter.


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  • Elyse

    Awesome article! Very use friendly and you explained things so simply! Thanks Thrifty Traveler!

  • Great article

    • Thanks Stephanie! Keep reading. We should have some more great tips next week!

  • I have good experience with Kayak Flights. Thanks for sharing. I will give thumbs up to Kayak Flights