After I booked my round trip ticket to Russia for $400, I have had multiple reach out to me about booking flights and how to find deals. So, I figured to was about time to write a little guide about my process. In addition to my Russia flight, I have also managed to find roundtrip tickets from Kansas City to Belize for $250 (which I booked!) and multiple flights to Europe for around $500-$600 (which I’ve booked 2 of. Whoops.). So let’s get right into it…

Secret Searches

When looking for flights, always make sure that you are using a secret or incognito window. There is a reason that flights seem to be more expensive the 2nd, 3rd, or 78th time that you look at the same route. Your browser’s cookies let websites know that you are looking at flights to a certain destination. They then hike up the prices each time you look at that flight in the hopes that you will book the flight before the price goes up even more. You can go to File -> New Incognito Window or use the keyboard shortcut Command + Shift + “N”.

Airline Miles

Every time you book a flight you should be earning miles. That’s just free money you’re letting slide by. I also tie my credit card rewards to airline miles and get double dips on hotel rewards sometimes too. There are three major alliances: Star Alliance, Oneworld, and Sky Team. Try to pick one and stick with it at if all possible. I use Sky Team whenever I can, with Star Alliance being my backup. I also earn miles with Southwest which is my preferred airline within the USA.


Two types of flexibility: Dates and Locations. If you can be flexible with at least one, preferably both you can save a ton.  I like to use Kayak to double-check that my flight isn’t cheaper 3 days before or after my selected dates. Lonely Planet’s Essential Information page is also a good place to check out when that destination’s high, low, and shoulder seasons are. I prefer to travel in shoulder season because the weather is usually pretty good, there are fewer tourists, and prices are lower.

If you can be flexible with your location, you have the best chance of finding a steal. If you have no destination in mind, I recommend using Kayak’s Explore feature. You can set your price, a month, even the weather, and it will tell you what destinations fit the bill. It’s really wonderful if you just want to see the world. If you already have a destination in mind, see if it is cheaper to fly to a different airport in that city or to fly into a different place altogether and use a short regional flight or a train or a bus to get to your desired location. This is especially true in Europe, where it is normally cheaper to fly into a major hub such as Dublin, Paris, Istanbul, Warsaw, or Amsterdam and then catch a Ryanair flight to your final destination. Which brings me to my next tip…

Budget Airlines

If you’re willing to give up some comfort (think leg room, food, drinks), budget airlines can be a great option. You notice I say can be, this is due to a few things. 1. Budget airlines usually fly out of the airports located outside of town. 2. Budget airlines will charge you for every piece of luggage and it must meet their exact requirements. 3. If you don’t follow their rules, there are hefty fees involved or they might not let you on your flight. For example, Ryanair in Europe requires you to print off your own boarding pass before hand. It costs 15 euros for them to print it for you. Frontier requires you to be checked in 45 minutes before the flight leaves or they won’t allow you on (I learned this the hard way). 4. If your plans change and you need to cancel or modify your flight. There will be a hefty change fee or no refund.  But if you travel light, follow the rules, and know your plans won’t change, budget airlines can be a wonderful thing!

One Way Flights

If you are planning on traveling to a few destinations, it is often cheaper and easier to book 2 one-way tickets instead of backtracking to your original destination. It gives you more flexibility as well. This is especially true if you’re trying to squeeze in a few countries in a short time frame.

Know Your Tolerance Level

For someone like me who loves to find a good deal, this is hard. A long layover is not always worth it. An overnight layover on your way home is most definitely not worth it, especially if you’ve been traveling for an extended period of time. Between your sanity, comfort, and the money you would spend feeding and entertaining yourself at the airport, you might spend more than it would have cost you to book a direct flight.

The Flight Deal

Alright. Here’s my big secret. My favorite way to find flights. The Flight Deal. They only publish fares that work out 6 cents or less per mile. They literally do all of the work for you! I follow them on twitter so that I get instant updates on new deals. You’re welcome in advance.

Mix and Match Tips!

There is no right way to find the cheapest flights. Sometimes you have to use multiple of tricks. Sometimes you luck out and find a super cheap flight on the first try. Personally, I don’t usually have a destination in mind, so I start with the Flight Deal and look for a destination that interests me. Then I either use airline miles (Southwest) or a budget airline to get to the departing airport (usually a big, coastal city like LA or NYC). Sometimes I play around with the flight I found on the Flight Deal to see if it’s cheaper to fly out of Kansas City or Omaha (my local airports) than using miles or paying for the regional flight. Just play around with your searches until you find the flight that is best for you. Booking your flight is one of the most important parts of planning your trip, so don’t rush the process.

Do you have any other tips that you swear by? What is the best fare you’ve ever booked? Let me know in the comments!


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