How to Book Cheap (or FREE!) Flights

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How to Book Cheap or Free Flights

There are several ways to save money when booking flights – most require you to be somewhat flexible, however. Usually I plan a big trip somewhat far in advance – even a year out sometimes. (Other times, I’ll plan within a week, which can also work out in my favor). Don’t be hasty when booking your flight (unless it’s a steal, of course!) Check flight prices frequently and on several different sites. This is how I usually go about booking a flight:

NOTE: Kayak, Skyscanner and Capital One did NOT pay me to write this, although they probably should.

1. Check Kayak.com (my go-to) for flights on the dates you want to go (and always mark the “flexible +3 day” option. Tuesday – Thursday tend to be the cheapest flying days).

Kayak Flexible Dates
Screenshot from Kayak.com

2. Check Kayak for the same flight but in a few days to a week from now. This will show you if there are often last minute/discount tickets available.

3. Check Kayak for tickets in a year/very far in advance to see if buying ahead of time will benefit you. Overall, #1-3 is so you can get a general sense of how much tickets should be/what the average price is.

Kayak Price Watch
Screenshot from Kayak.com

4. Check Kayak’s suggestion if you should buy or not (they collect data and will often tell you if you should wait or buy immediately, depending on how prices have been in past weeks/months/years. This is a graph that will show up on the right sidebar (but won’t appear for every search). You can also create a price alert where they’ll email you when the price changes for your specific search.

5. Do #1-4 again on Skyscanner.com (yes, prices will sometimes vary and they will sometimes show different airlines).

6. Try the “flexible/everywhere” option on Skyscanner. If you’re pretty flexible and can do a layover, sometimes it’ll be cheaper to fly to a nearby country, explore a couple days there maybe, and then catch a budget airline or train to your destination. This option will let you enter where you want to fly out from and will show you the cheapest flights people have purchased to basically anywhere in the world.

Skyscanner Everywhere
Screenshot from skyscanner.com

Skyscanner Everywhere Search
Screenshot from skyscanner.com

What I don’t like about it, is that these are just flights people have found, but when you click on them, they’re often higher than the price they show on the original search results page. However, it’s a good way to find airlines that have cheaper flights. Sites like Expedia and Kayak won’t show every single airline so it’s always good to explore other options. This option is also good for when you’re planning a trip and trying to decide where to go!

7. After doing #1-6, you should be able to get an idea of what airlines have the cheapest deals. This is when I go to individual airline’s websites to check prices (usually the cheapest 2-3). They’re sometimes cheaper than the prices on Kayak or Skyscanner.

8. Repeat #1-7 for as long as you’re willing to wait. If you see prices start to go up, then maybe go for it. If it’s still more than you’re willing to pay, take your chances and wait it out. I’ve been doing this method for years now and will usually end up buying within 2 months of my departure date (and most were bought within 3 weeks!) It’s not always true that buying it as far in advance as possible will get you the cheaper rates. Last minute tickets are often the least expensive.

NOTE: I use this method more so for long haul flights. I’ll do a similar process for shorter/cheaper flights but not as elaborate or as frequently. Also – these are just the steps I tend to follow and have worked for me. No hardcore research was done.

How to Book FREE Flights:

•  Use a credit card that will give you miles. Tons of sites will tell you how to do this in more detail (head over to the Frugal Travel Guy, which is where I began). I use the Capital One Venture card – if you spend $3000 in the first 3 months, you get bonus miles that essentially earn you a $400 flight (on any airline, or $400 worth of any type of travel expense). Use this card for your bills, rent if you can, and everything else and $3000 should be no problem. These types of cards tend to have a high APR so either do a balance transfer or pay it off in full each month.

Venture Credit Card Rewards
My $390 LA – Madrid flight REDEEMED! Screenshot from capitalone.com

⇒ The Capital One Venture Card makes it super easy to redeem your travel expenses. You just sign in online, go to your Rewards page and it will already have all of your “travel expenses” listed, along with how many miles you have and how many miles each transaction is! Then you can choose any of them to redeem (which include anything travel related, even Lyft!) and voila – it’s credited back to your account in a few days like it never happened!

Other Tips to Save Money When Booking Flights:

•  Round trip flights are usually a better deal than one-way tickets.

•  Peak season (summer, holidays) will be the most expensive time to travel (including flights, hotels and activities). Obviously you can’t change the date of your best friend’s wedding in Hawaii, but when booking your vacations, remember to research when the low season is!

•  For budget airlines, they often have promotions – check these frequently if you’re super flexible and enjoy booking spontaneous trips :)

•  Always check how much it will cost to check luggage (or don’t check luggage at all!). Airlines like Norweigan Air will have insanely cheap flights but will then charge an extra $50-$100 per suitcase. Obviously if you’re moving to a new country, you’ll need to check luggage, but if you’re only traveling for a week or two, try to keep it to a minimum! Also, make sure you’re considering luggage fees if you’re breaking up your trip with a layover or switching airlines.


•  Check luggage weight allowances as well. Some airlines are brutal and overweight luggage fees can be extreme. Many will also weigh your carry on and force you to check it if it’s over the maximum weight (usually it’s 7, 10 or 15 kilos – so make sure you check on their website) – budget airlines like Air Asia and Tiger are notorious for this!

•  You get what you pay for!! Budget airlines can be sketchy and flakey. Air Asia has cancelled my flight a week before and did absolutely nothing to try and help me get a new flight (they cancelled the entire route altogether). Just be wary! And if you’re booking connecting flights separately, make sure you have a good cushion of time in between, in case of delays.

•  Check other modes of transportation. For instance, flying around Southeast Asia can be pretty cheap but buses and trains are often much cheaper. Traveling overland also has the benefit of not having to worry about luggage weight/baggage fees.

Happy flying :)

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1 Comment

  1. Christina Wells says: Reply

    Kirsten, look at you go!!! Excellent work!! Great read!

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