Almost Fearless

The Not-So-Secret Trick to Finding Cheap Airfare: Day 15 of 30w30d

This post is part of 30 Ways in 30 days to Redesign Your Life and Travel the World. This series seeks to give you the practical, real world steps you need to take to get from wherever you are, to exactly where you want to be– traveling the world and living the lifestyle you want.


30 ways in 30 days, airfare, savings, deals, travel around the world

I’ve seen two ebooks published on the subject this year alone.  How can you find those super-cheap airfares?  There is no secret.  It’s all about flexibility.

You’ll pay more for:

  • Flights on Monday/Friday/Sunday
  • Flying the morning or at night
  • Flying non-stop
  • Traveling in certain seasons (for example to Europe during the summer or to Hawaii during the winter)
  • Buying too early (more than 5 months before your flight)
  • Buying too late (less two weeks before flight)
  • Certain Destinations (NY to London is cheaper than NY to Dublin, yet almost same distance)
  • The day you happen to buy– who knows the next day the airline may adjust prices

So how do you find cheap flights without spending hours running multiple searches?

Passive Search

I’m personally a big fan of Kayak (apparently so is Microsoft) for it’s flexible, anywhere in the world, any time frame searches.  You can search by a continent– say EUROPE, and they’ll give you the cheapest flights by country.

So instead of checking each country– trying to find a good deal– they give you all of them at once.  You pick where to fly based on what’s cheapest.

I recommend setting and leaving a few of these fare alerts so that they will send you weekly email updates and keep you passively aware of the marketplace.


  1. Go to
  2. Pick your home airport, a destination continent and a timeframe (by the month or leave it as is for “anytime”)
  3. I picked NYC to EUROPE for NOV 09 and had some surprising results: The cheapest three flights are:$481 to Moscow, $497 to Dublin, $509 to Geneva.  This tells me that a flight to Europe for under $500 is probably a pretty good deal.
  4. Click the “Get this by email” link to schedule a fare alert direct to your inbox.
  5. Repeat with other areas of the world as needed.    I set one for Asia and found deals in India on the top of the list at about $720.  South America had a flight to Peru at $347.  I’m starting to get a sense of the relative costs.


When a good deal comes, don’t wait.  Cheap prices in one market usually means that the other airlines will rush in the next few days meet the price.  Even if you’re not flying that exact day, it’s worth doing a quick price check across a few sites.


  1. Search the airline’s site and make sure they are in fact offering that price.  (And if you’re flying one-way to make sure their one-way price isn’t wildly expensive).
  2. Do a quick search on Kayak for the same flight, and then check the second and third cheapest option’s websites to see if they are offering cheaper deals.
  3. If it’s a long haul flight, you’re done.  If it’s a short flight, say Madrid to Paris, you’ll want to check local carriers, like RyanAir, who might not be listed in the search sites.  A google search for your flight area will usually bring up a few local search engines you can double check.

Don’t Worry Too Much

Spending hours trying to figure how to save $20 on a flight will drive you crazy and waste your time.  The truth is that the pricing mechanisms are complex and don’t always follow the so-called rules.  If you can get a good price, lock it in.


Christine Gilbert

I’ve been dragging my husband around the world since 2008 always with the promise that, “Yes, Drew there will definitely be hammocks there.”



  • Hello Christine, I knew about Kayak before but the feature called Buzz is new to me. And incredible as well. In the past few months (years?) I’ve been struggling to find the best deals and I always dreamed of a tool like this. Fortunately, it exists. 🙂

    Thanks for sharing!
    .-= Guillermo Guerini´s last blog ..Heating up by the warm syrians and the chaotic Aleppo =-.

  • Be careful with using budget airlines after a long-haul flight! They’ll tend to have very severe weight restrictions and will always charge you for any bags you want to put in the hold. You get ONE carry on bag, not the usual one carry on and one purse deal. So, unless you can pack everything you need in a tiny bag, you’ll end up paying the difference between a budget airline and a regular airline purely through penalties on baggage.

  • How do you search for EUROPE (or for any continent) in Kayak? I tried just putting that in the Destination field but it didn’t work.

  • Microsoft’s new Bing search engine makes use of “farecast technology” which shows you an indication of whether the price for the airfare you’re looking at is expected to go up or down in the near future.

    You can see more about it here:

    Also, I found to be very useful when I was traveling in Asia and Europe. It lets you plug in a starting point and destination, and then lets you know which discount airlines fly that route.
    .-= Dave´s last blog ..6 Tips for Reaching the Greek Islands =-.

  • Golly gosh – this blog is suppose to be huge but offers little ……

    If you want cheap flights check out or if you can go anytime try and submit a bid for travel to your destination and approx time periods.

    Signing up for various airlines webdeals e-letters offer some possibilities.

    Also try,,, skyeurope,,, easyjet – some one ways ar cheaper than returns, some flights from slighter less convenient airports are cheaper, red-eye flight East-West across North-America.

    flying mid-week is often cheaper, Airlines sales can be for days only – have to keep you eye on sites all the time.

  • Dingo– Supposed to be huge? I don’t know where you get your information 😉

    Thanks for the links. I think most people are aware of the major search sites, but I was trying to give a tip that AVOIDED having to search a few dozen different sites. Also, I mentioned mid-week flying as cheaper (plus a bunch of other things).

  • yeah, some blog mentioned you.

    Yes, you did mention mid-week, getting bumped can help b/c they either pay you a lump sum or give you a free flight -sometimes I ask first if its a long-haul although its obviously not how to get a cheap ticket but how you can get money back out of the one youve bought!

  • […] Today marks her 20th day in the series, and even if you don’t harbor a desire to drop what you’re doing to live at large in the world, reading her steps toward being location independent can uncover whatever dormant lifestyle shifts that are begging to be released in you. I personally enjoy Day 16: Becoming a Digital Nomad, The Freelance Edition as well as some assorted tips from Day 15: The Not-So-Secret Trick to Finding Cheap Airfare. […]

  • Great post Christine,
    One thing to add: don’t jump on a cheap fare, pay for it with a credit card and then wait for months to pay off the balance. You’ll inadvertently spend your airfare savings on credit card interest fees.
    .-= wandermom´s last blog ..Family Skiing: Three Cost Saving Ideas =-.

  • Definitely a good post. Surprisingly so. Amazing that europe is only $500 away isn’t it? 😀 Cool stuff. Your point about not spending hours to get slight discounts is a good one, but I actually found wayyy more helpful than I expected it to be. Worth the time and money to acquire skills that will save you money for a long time to come. There’s nothing more fun than traveling smart and being able to travel more as a result!

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