The Definitive Guide To Buying Cheap Flights In 2019

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Flights are going to be cheap in 2019. In fact, flights are cheap right now. What’s up, shoulder season?! Flight watchers like Hopper have January flights dropping by up to three percent this month and slowly rising again, starting in February. But it’s not as simple as logging onto your favorite airline’s webpage and just paying 50 bucks to get across the country.

While flights around the world are currently priced more aggressively than ever, you have to shop these flights. To score incredible deals you’ll want to keep a keen eye on sales via flight aggregators. You have to be smart about when you buy a flight (no, we don’t mean hitting “purchase” on Tuesdays, that’s a well-debunked myth). You also have to stop procrastinating and sign up for loyalty programs and switch to travel-focused credit cards for purchases; otherwise, a lot of this is just idle talk.

If you’re looking for that amazingly cheap flight in 2019, then follow the advice below. You will find a great deal. You can get those prime upgrades. The open road is waiting for you.


This is the most important step by far. Real talk: You can have all the right credit cards and loyalty programs. You can check on the price of your dream vacation every week. That’s simply not good enough to score a cheap flight. As a civilian who has to work, sleep, and do shit besides spending all day and night looking up flight prices you are never going to be on at the right moment to score that cheap flight deal.

Luckily, we live in a world where valiant folks are running feeds and websites devoted to being on top of flight prices all day and night. Twitter feeds like Airfare Watchdog are crucial to getting pinged with great flight deals literally all day every day. Websites from professional travelers like God Save The Points also offer great tips and deals on flights in an almost constant stream. Then there’s Scott’s Cheap Flights which will send you a constant stream of emails after you sign up. Trust us, this service is essential if you’re looking for a cheap flight and don’t have the time to sit online all day hitting refresh in incognito mode.

At the end of the day, the best (right now) is Secret Flying. Follow their Twitter and Instagram for a constant stream of deals all over the world. Set up those alerts for your dream destinations and your home airport. Before too long, something will pop. We’re also fond of Uproxx’s own Cheap Flights page, which rounds up the cheapest flights and best deals of the week, every week on Travel Tuesdays.

The point here is: Follow the people and apps that are watching the prices and be ready to pounce when you see that crazy cheap deal.


The idea of a travel agent in 2019 seems a bit outmoded, silly even. But, in reality, online travel aggregators like Kayak, Momondo, Skyscanner, Expedia, and Google Flights are basically just digital travel agents. You input your travel desires and the algorithm gives you your options.

Each of these sites has their own benefits. Expedia often runs great coupons that can save you up to 50 percent off flights during certain sales (and 90 percent off hotels). Kayak, Google Flights, Skyscanner, and Momondo all have a calendar and/or map options so you can find the absolute best dates and nearby airports that might be cheaper.

If you’re looking to go to a specific place around a specific time (which is a reality for most travelers), this is your best bet to dial in the lowest prices around that same time/place. You may not get that crazy cheap roundtrip to Europe or Asia but you will certainly be able to shave dollars off the price.


More real talk: You’re not scoring that crazy cheap flight unless you’re 100 percent flexible about where you’re going and when. Sometimes you’re going to get lucky and Secret Flying will pop off with that perfect flight deal right when you want to travel. Don’t count on that though.

To really score the best deal, you have to know your budget and wait for the cheap flight to a place that sounds cool. Then you have to work around when that deal is actually available. It might be September instead of May or winter instead of summer or the rainy season instead of beach season. The point here is to be flexible and ready. If you really don’t care about where you go as long as it’s just somewhere, then the whole entire world of cheap flights opens up to you.


Okay, let’s say you’re not going to wing it with the Secret Flying style shopping. You have a place in mind. You’ve saved your cash. It’s time to make that dream a reality. That’s cool. Book early.

Most sites and aggregators which study when to buy a flight (in an average situation) say six to eight weeks out is the money spot. A big word of warning here: This is an average. Sometimes flights are at their lowest when they first come on the market which is up to 12 months out. This is why Kayak offers a chart to show its expected trends on ticket prices. Y

Again, all of this is very squirrelly with a lot of “buts” and “yets” and “maybes” abounding. One thing that most groups who follow this sort of thing tend to agree on is that buying a flight within a seven-day window of departure is almost always the worst time price-wise.

Lastly, don’t give up. Deals, sales, and coupons pop off all the time these days. Be smart about major holidays and sales times. Spring sales, Black Friday/Cyber Monday, summer, winter, fall, President’s Day, Fourth of July, etc. will all be days/weekends/weeks when somewhere a sale will be happening in some capacity. So be more aware and engaged with the feeds and websites around these times.


It’s on you to shop for flights. Twitter alerts are key but not just for Scotts Flights or Secret Flying. You can set up email alerts with all the major flight aggregators from Kayak to Skyscanner.

You have to keep an eye out, do the research, check your alerts, and be ready to buy. These deals after often only last for an hour or less. If an error fare pops off, you may only have five minutes to make a decision.


No one is going to hold your hand here, especially not the airlines. Budget carriers are going to charge you for seat reservations, carry-on luggage, checked luggage, water, food, WiFi, and maybe even entertainment. So that amazing $300 roundtrip to Amsterdam might end up costing you $100 to $200 more each way. Our travel editor recently told a story about a Norwegian flight where he was scrambling and didn’t bring food — so he ended up spending $40 on Cup O’ Noodles. That’s rookie shit, you gotta know who you’re dealing with.

The best example of this is Frontier which often has one-way tickets around America for $20. That’s sans carry-on and right away you have to pay another $35 to bring a single carry-on bag. This is becoming the norm more and more.

Pro tip: if you see an amazing flight deal with a major international carrier (KLM, BA, Singapore, Cathay Pacific, Iberia, etc.), buy that ticket. The major carriers are starting to run crazy cheap deals to destabilize with the budget carriers (Norwegian, Wowair, Ryanair, etc.) with a big ol’ caveat that they still offer free meals and booze on int’l flights, free seat reservations, free carry-ons, and often at least one free checked bag. If you see these, snatch them — the in-flight experience on KLM is miles better than Wowair.


We can’t stress this enough: Only buy travel with a travel reward credit card. If you’re not making points with both the bank and an airline or hotel group, you’re literally leaving money and perks on the table. 2019 is the year to stop doing that.

This one really comes down to where you live and what airlines you use most often. In the end, it means you can accumulate rewards points that’ll give you cash back or upgrades or even free flights throughout the year. It also usually means that you won’t get any foreign transaction fees when you’re on the road. Another big win.

Our advice here is pretty straightforward. Get one of these cards and use it for your everyday expenses. Then pay off the balance at the end of the month with the budgeted cash you would have spent anyway. You’ll start building points like fire. Then you can start using those points to actually travel within a year.

Big credit card companies like American Express have a long list of cards for various types of travel. We like this one because having an AMEX grants you access to American Express airport lounges around the world. That’s a huge perk. Most banks from Bank of America to Wells Fargo to Chase offer cards with various possibilities for points and rewards. Chase Sapphire Preferred is beloved by travelers for its low annual fees, great signing bonus, solid perks package.

It’s best to look at your current situation and adjust accordingly.


Lastly, folks, sign up for all the loyalty programs. If you’re flying with Spirit, sign up. If you’re taking a BA flight to London, sign up! It doesn’t matter if you don’t think you’ll ever fly that airline again. You may. Still, all the major airlines are part of larger groups — Oneworld, SkyTeam, Star Alliance — and that means those points are transferrable to loads of other airlines. Airlines you’re likely fly at some point in the future.

Besides collecting points that you can use for upgrades and future free flights, there’s another huge benefit here. Airlines are going to treat you like a valued guest. You’ll no longer be at the bottom of the passenger list — i.e. the first to get bumped. You’ll also be the first in line for free upgrades at the gate. You’ll build yourself to lounge access and fast track security services. It all adds up.

At the end of the day, not being part of a loyalty program (especially for an airline you fly often) is literally leaving cash and benefits on the table. Don’t do that in 2019.