My First Three Steps for Getting the Cheapest Flight.

I finally did it. I purchased the actual ticket. I got a flight with WiFi, decent layovers, an evening take off AND an evening landing — all for only $824.

It doesn’t sound like a good deal, but all other flights for this path start at about $1000. So how did I do it?

I made a video a couple of years ago about this very topic that has some more details, but here are my first three steps for getting the cheapest ticket possible. If you need any help or advice, you’re welcome to reach out to me on Twitter or Facebook.

1)Decide the dates, or date range, if you have flexibility. I had initially decided on January 2nd so that I could have a clean break regarding taxes and not have to mess with 2017 earnings at all, but I postponed it by a week. First, because apparently I can earn up to $399 through Uber before having to claim it so I might as well. And second, because I want to allow myself enough time to wrap up everything here. Selling a car, subleasing an apartment, and reducing/storing all of my worldly possessions may be a bigger task than I am anticipating. I don’t want to be a panicked mess when I embark on this new chapter.

2)Browse websites obsessively. ***ON INCOGNITO MODE***
I always start with Kayak, because they have a really good comparison grid.


It’s cool to see how one day difference can save $300. You can go through so many options by just plugging in the dates and glancing at the color-coded grid.

My second website is Skyscanner which is really popular among the travel community. You can put in as much or as little as you want in order to search flights. Not sure where you’re going? No problem. Not sure which day you want to go? Check out our handy calendar.1

The only thing that I don’t like about their website is that so many dates are magnifying glasses. I like to see it all at the same time and having to actually search a date individually is a little annoying. This generally isn’t a problem for more popular routes and for dates that aren’t so far out, but I’m just a lazy crybaby who wants everything to be handed to me on a shiny, color-coded platter. Don’t judge.

My third website is one that I just started using. Google Flights is easy to customize, easy to read, and easy to navigate and has the potential to be my new favorite.1

At the top of this image, it gives you the option to toggle between different views.
Calendar like Skyscanner? Check! Comparison Grid like Kayak? Check!
AND an easy to read bar graph! I really appreciate the simplicity and the different views. My only concern is that it won’t search for dates greater than 30 days apart. I recognize that most responsible adults don’t take vacations longer than two weeks so this isn’t a problem for the vast majority of people, but it’s nice to have the option of a few months.

These three websites were my main hobby this past week. I combed through them every spare minute to see if I could find what I was looking for. The reason that I strongly recommend that you use incognito mode is because many of these websites will remember your search history and it’s not uncommon for them to raise the rates if they think you’ll be buying the ticket soon.

3)Pay close attention to take-off/landing times as well as layover duration and locations. I saw a ticket for $668. $668! But it was a 40 hour journey with long layovers in airports that I didn’t want to go to. For some this would be ok, but I’ve done that before. A couple of years ago I found a cheap ticket that had a 22 hour layover in Zurich which I thought was amazing. I won’t go into details, but it was not as glorious as I had anticipated. I did, however, get a nice assortment of scenic photos because Zurich is beautiful.

I’m not too picky about flights but I do have a few things I will not budge on. I will not have a layover more than 5 hours long in an airport with terrible reviews. I’m very flexible on departure time, but I refuse to land in a new place at 3am (partially for safety, partially because there won’t be any good restaurants open). I sound like a diva right now, but I feel like these are pretty normal concerns.

If you have any questions or need help or advice booking a flight, let me know. 67 days!


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