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. Let’s run down exactly how to book the cheapest flights possible.


My favorite flight searching tool: Google Flights 

Google Flights is the best flight search engine. All you need to do is enter a departure city and destination, as well as sample dates, and you’ll have access to the powerful 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.


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’ 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. Another powerful 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. Click here to learn more about how Momondo finds the cheapest flights.

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.


Thrifty Traveler Premium

We’re always keeping an eye out for the best flight deals. To get instant emails for the best international flight deals, make sure to subscribe to Thrifty Traveler Premium.


Points and Miles

I rarely book a trip without using points and miles. Even 1-2 credit card sign-up bonuses should be enough to cover the travel costs for you to fly anywhere in the world. Check out our Beginner’s Guide for more details.


Bottom Line

Booking the cheapest flight possible is as easy as following the steps above. We find an incredible amount of flight deals, 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. Our mantra is book now and ask questions later!


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