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A cheapskate’s guide to affordable air travel

8 keys to finding the cheapest vacay.


Jam Kotenko


Posted on Jul 4, 2015   Updated on May 28, 2021, 10:33 am CDT

Traveling is the best kind of hobby—it breaks us from our routines and plugs us into the world. We return with epic Instagram pics that last a lifetime. Unfortunately, for most people, it’s also a huge luxury.

How to Find the Cheapest Flights Every Time

Inspired by this viral photo gallery that hits on some critical principles, we’ve decided to put together a handy guide you can bookmark for those days when you are just itching to GTFO of your city and be somewhere exotic.

1) Do some research, duh. And do it early.

The sooner you realize that looking up cheap flights for tomorrow is a futile endeavor, the better. Look up flights at least a week prior to your desired departure.

Start by trying these services to find the cheapest air fare and find one that works best for you.

If you fly frequently and have memberships to mileage programs, AwardWallet is incredibly useful in tracking points.

A great app to use for booking non-flexible flight dates and destinations is Hopper, which allows you to enter a route and gives you an idiot-proof “when to book and fly” guide.



As an added bonus, here’s an out-of-the-box pro-tip we received on Twitter:

Doing it on a flight from Pittsburgh to San Francisco revealed identical results on both pages so I can’t confirm if this tip actually works (it might be a case-to-case basis), but there’s no harm in trying it. It takes a measly second to open that extra tab.  

2) Don’t be hoity-toity.

Don’t say no to long (or several) layovers or red eyes, for they are likely your wallet’s biggest allies. Flying direct is the most expensive thing to do when it comes to traveling, so open yourself up to plane-hopping. SkipLagged is a great platform—which actually works so well that some airlines absolutely hate it—to use for assembling affordable flight legs. Another is CleverLayover, which combines flights from different airline companies.

Red-eye flights—or flights in the wee hours of the morning—are probably your cheapest bet because people don’t like them. But so what? The only ones willing to resort to booking them are certified badasses. Be one. (And bring a comfy travel pillow, maybe some Melatonin.)

Oh, and don’t pack a bag that you’ll have to check. That’s usually extra.

3) Break up the band and go solo.

You don’t need your gal pal as your seatmate. Be adventurous. Learn to have fun by yourself and book your ticket solo. You can always hook up with your people upon landing.

4) Set your destination expectations low.

Does your travel plan boil down to: whenever, wherever? Then make the smart decision to travel to cheap places. Why spend more than $2,000 to fly to Paris when you can save almost $600 by heading to Ukraine or Bucharest?

If you’re shopping around for potential vacation places, Hitlist lets you set alerts for trips with variable dates and/or destinations. Using the app, you can set up an alert for things like a 10-to-14-day trip to Europe in late July or early August; additionally, installing its nifty Chrome extension will constantly remind you of places you ought to be at and what ticket prices cost if you book yours today.

Another resource for insane travel deals? Groupon. Don’t laugh.


5) The more unknown the airport, the cheaper the airfare.

Always check the “include nearby airports” box on whatever search platform or app you are using. Look up alternate airport codes to use for your price alerts. Taking additional public transportation to get to your destination adds character as well as adventure.

6) Don’t make Friday your flight day.

There’s no exact science for picking the best day to fly. Using common sense, however, remember that most people only have the time and the liberty to fly at the end of the week due to work and family obligations. Plan to fly midweek and return on a Monday.

7) Use an airline-affiliated credit card.

If you’re racking up debt to make an expensive pastime happen, you might as well earn something back. To get you started, Southwest Airlines is with Visa, while Delta Airlines is with American Express.

8) Sign up for all the airline newsletters.

We’re not going to lie: Airline newsletters are annoying and will inundate your inbox with spam. But if you make Gmail your bitch and sort through all the bulk, it’ll be worth it because it’ll lead you to pages like this:


H/T Imgur | Photo via David Becker/Flickr (CC BY 2.0)

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*First Published: Jul 4, 2015, 12:50 pm CDT