How to Book the Cheapest Flight

December 2, 2013 — 13 Comments

After traveling for work for ten years and a nine month trip around the world, I’ve collected some strategies for traveling cheaper. I’ll cover them in a ten part series in this order:

A. The flight
– How to Book the Cheapest Flight
– How to Use Free Flight Stopovers
– How to Find Alternatives to Expensive Flights
– Finding the Cheapest Airport Transportation
B. The Hotel / Accommodation
– How to Book Cheapest Hotel Rooms
– How to Find Hotel Alternatives
– How to Use Hotel Points
C. Arriving
– How to Get Local Currency for Your Trip
– Avoid International ATM Fees!
– Know How Much Things Cost

How to book the cheapest flight

Flights can easily represent one of the largest expenses of a vacation, so it pays big time to do a little more research to try and save money.  There are a few strategies you can use to save money on flights while traveling.  Here are my recommendations for finding cheaper flights.

The Booking Site

It all starts with the booking website.  There are quiet a few out there, but for all of our travels, I primarily visited two sites – and  Here is a quick review of each: searches multiple websites to make sure you get the best price.  They search directly with airlines as well as reviewing other booking sites to find the best deal.  What I like best about Kayak is that it’s pretty easy to make quick changes to your search to see how prices change.  For example, you can do a “plus or minus 1 or 3 days” to see if prices are cheaper in the days around your intended travel.  It also easily lets you search from nearby cities. has a great smart phone app and recently updated their website which used to be quite archaic.  However, anything they lacked in their  early usability issues, they more than make up for in their ability to find you cheap fares!  It’s become my go to search engine for booking flights and the app makes it really easy to see prices across multiple dates – much easier than the website.

how to book the cheapest flight = Skyscanner

Skyscanner’s website – I still prefer that smart phone application

Strategies for Finding Cheaper Flights

Now that you have the tools for searching for cheap flights, let’s talk strategy. Here are some of the steps I use to make sure I find the cheapest flights.

A.  Check alternate airports

This may sound like a painful thing to do, but many cities across the US and across the world have multiple airports.  Kayak will check these automatically, but you’ll need to check each airline manually when using Skyscanner.  If you do find a better price at another airport, make sure it’s still easy to get to your destination or it may not be worth it.

B.  Check alternate dates

As previously mentioned, Kayak and Skyscanner both allow you to easily view alternate dates.  We’ve easily saved hundreds of dollars by waiting a day or two so if you’re flexible, this can definitely be worth it.

how to book the cheapest flight - Skyscanner phone App

Here’s an example of Skyscanner’s iPhone app and how it lets you search fares across multiple dates.

C.  Check flight prices throughout the week

Flight prices can change very quickly and it’s worth it to monitor them for a couple of days (or weeks) to see if prices change.  Kayak also has a great chart that shows you how the price has changed over the previous weeks and gives you a “% confidence” of whether you should book at the price or not.  Some airlines even let you hold a flight for 3-5 days with no cancellation fee which is great because you can hold it, check for a few days, and then book it if your original price still seems good.

how to book the cheapest flight - Kayak Price Graph

The circle is highlighting Kayak’s “Price Trend” which shows you how your fare has changed over time and gives you advice to buy the ticket or not.

Do you have any recommendations on how to book the cheapest flights?  If so, I’d love to hear your tips in the comments!

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13 responses to How to Book the Cheapest Flight

  1. This will come in handy when we get to a point when we can travel again.

  2. These are awesome tips Dan. I started using some of these tips no long ago and they really do save you a ton of money on airfare. It also helps if you are flexible on your dates and times of departure. 🙂

  3. Dan-
    Check out this site:
    This is what I’ve been using over the past year. I believe it’s the “backbone” of most all of the travel/airfare sites out there. It allows you to do a search with multiple departing airports and multiple arrival airports. It also allows you to identify how many stopovers you’re willing to take, flexible dates, various currency rates, etc. You can see a whole month’s worth of the cheapest flight options based on your inputs and the number of nights you would like to stay (it can be a definitive amount or it can be a range; i.e. 3-5). It also allows you to search for one-way and multi-city connections.
    While you can’t book directly with this website, it will tell you all the details you know in order for you to go to the individual airline’s website to take care of that. I’ve found it very useful and hope you do too.

    Glad to have you back in the States and I’ve enjoyed reading about all of your adventures!

    • Wow, I really like that site, thanks for mentioning it! Does it work well with domestic and international travel? It’s definitely good to be back, we’ll have to catch up soon.

  4. P.S. the “I’m going to fight the English” phrase you threw into one of your posts definitely hit home to me….took me back to 224 S. Monroe circa 2003… 🙂

  5. One way I save money on flights in US is when going one-way to a major hub, I book a flight to any florida city
    and just don’t get on the second leg – this doesn’t work on roundtrips though because they’ll cancel the second leg of your flight.

  6. All great tips and ones to live by. Even though we recently got tickets to next year’s Oktoberfest using credit card points, my husband checked the flights every day for quite some time before we cashed in our points for the tickets. It really is amazing how the prices vary according to what day of the week users book them on. We decided to fly into Amsterdam and stay for a couple of days before taking an overnight train to Munich. All in all, it’ll be two weeks of traipsing through the Black Forest and other environs in the area. One bummer is that the Marriott closest to all the beer gardens isn’t accepting points. The only reason we were able to book a couple of the rooms was because of hubby’s “status.” Thank goodness. Okay, can you tell I’m excited? 🙂

  7. So nice to hear that you are back. I really enjoyed reading of your adventures. 🙂 I am busy trying to catch up with my blog commenting. So far behind….

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