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.

Some search sites are evil and gather information on how many times you have searched the same flight, and increase fare prices if you search the same flight more than once. Thankfully, Google Flights does not do this, so you should always see the lowest fare price. 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.


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. This isn’t a gimmick, you can save real cash!

One-way Flights

Before booking a round-trip flight, always search for what it would cost to book two one-way flights. You may be surprised to find out it may be cheaper, especially if  you are flying domestically in the United States. Most airlines don’t allow you to fly round-trip on two different airlines so you may be able to find cheaper one-ways on two different airlines! Searching on several airlines also allows you to have more date and time options for your flights. For example, it may be cheaper to fly Delta to your destination and then fly American back home, instead of flying Delta round-trip!


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.



Even though Google Flights generally has the cheapest airfare, there have been times when Kayak was able to find something cheaper. Before booking always do a search on Kayak, just to make sure you are booking the cheapest flight possible!

Another great Kayak feature is the ability to set up price alerts. You will receive a daily email on any price fluctuations.


Kayak Price Alert

Kayak Price Alert



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. Check it out!


The Flight Deal

The Flight Deal is another great site if you are hoping to snag a sale fare. Many of the flight deals they find only last a couple of hours but they are one of the best around. Book quick or you will miss out!


 Thrifty Traveler

We’re always keeping an eye out for the best flight deals nationwide. We also try to keep an eye on Mistake Fares as well! Make sure to subscribe to our 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. Seriously! 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 as is allowed by US Federal law. 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