How to Book Cheap Flights to Anywhere

I am cheap. Painfully cheap. This trait frustrates and embarrasses my fiancé to his core, but I can’t help it. I am, by nature, a tight-ass. I hate spending money in general but hate it even more when I feel that it is an unnecessary amount—for example, plane tickets. I travel because I want to experience a destination. If you ask me, which you have because you’re reading this, jacked-up prices on flights are highway robbery. The amount of money airline’s charge is absolutely ludicrous. Unfortunately, I’m not able to change the thievery of “standard” prices, so I’ve developed a set of skills to book cheap flights, and I’m happy to share them with you.

Over time and thousands of miles, I’ve picked up a few money-saving tricks when booking flights. This all, of course, came at a price. I learned the hard way, just as we all have. The money spent is long-gone, but I we can do better next time. Below are a handful of techniques I have acquired to book cheap flights. Good luck and safe travels, fellow cheapskates.   

Book Cheap Flights Traditionally

Google Flights  

This is the first window I open when researching flights. Google Flights is a one-shop stop to book cheap flights. It has everything you need with the exclusion of Southwest Airlines (bummer). It is, essentially, a super-duper search engine that allows you to quickly research flights without the hassle of opening a dozen tabs.

It is similar to Expedia and Priceline, but it includes everything because it’s not a competitor. It also has a great map feature that allows you to zoom out and see prices worldwide from your current location. If you’re flexible and indecisive, you can choose your destination based on price. What if there’s a wild sale on flights to Iceland? There’s only one way to find out: Google Flights!

Bonus: Set price notifications. When the price increases or decreases, you will be notified through your G-mail account. Again, if you’re flexible, set notifications for a handful of days and book your flight based on the drop.

Skyscanner  

This is the O.G. way to explore flights. Although this can be a bit sketchy because they deal with backyard airlines, the app is worth downloading. I have been able to book cheap flights through Skyscanner, but I always do my research before officially booking.

Skyscanner is a third party site, which means it funnels you to the airline’s main website. From there, I highly recommend becoming an expert on their cancellation policy, the cost of baggage, and if they charge for seats. I screwed myself with AirAsia by not taking this advice, so learn from my $370 mistake.

Southwest Airlines

Southwest is notorious for cheap flights, great deals, and two free checked bags. If your schedule is flexible, this airline has everything you need. As I’m writing this, there is a one-way Valentine’s Day sale as follows:  

From Las Vegas -> Austin $146, Denver $100, Portland $94, Seattle $86, San Diego $64, San Francisco $69  

This is my favorite way to fly domestically because I have accumulated points over the years, which pays for my flights. The free checked bags save me a minimum of $50 one-way when compared to other airlines. That alone makes Southwest my go-to.   

They also have recently added a handful of international flights: Mexico, Central American, & the Caribbean.   

Sign Up for Airline Rewards  

If you’re not registered with each and every airline you somewhat regularly fly, you’ve already failed. The points you receive for booking your flights add up quickly and pay off in huge ways! In 2012 I flew round-trip to East Africa with Delta. I received 18,000 points and didn’t use them until 2019. The points didn’t expire, and I was able to use them 7 years later.  

Side note: Normally, I book two separate one-way tickets with different airlines. I’ve found that most times, this is a cheaper option. Round-trip flights on the same airline with points or cash are excessive and sometimes wasteful, so I play the system.   

Example:

Las Vegas -> Tulsa (Delta) 12,000 points

Tulsa -> Las Vegas (Delta) $330 or (Southwest) $150 or 12,000 points

Obviously, I chose Southwest for the flight home, and again, used points. That is a round-trip flight for $0 

Southwest Rapid Rewards = FREE Flights

On that note, Southwest Rapid Rewards is my favorite point program, partially because I have the Chase Rapid Rewards Credit Card. When I signed up for the credit card, they had a promotion for 50k points if you spent a specific dollar amount in three months. With rent, utilities, and wine, that was 100% attainable. With that 50k points, I was able to start with a strong foundation, and I’ve been flying for free ever since.   

At a minimum, I receive $1 for every dollar spent, and that, plus promotions, add up. I am now at 80k points and rising. I used my points to fly Bozo and me to Cabo San Lucas (which was a nightmare) for free and still had plenty to spare.   

The trick is to wait for a sale, which they have monthly. Southwest, in my opinion, has the best bang for your point buck. They regularly have one-way flights from Las Vegas to California for $49, equal to around 2k points! Play your cards right, and you’ll fly free for eternity.   

If you don’t have or want the credit card, you still earn points from flights flown, rental cars, and hotel stays. I highly recommend checking Southwest for all travel plans before other sites. This has saved me thousands! 

(This is not a sales pitch. I do not recommend signing up for a credit card if it is not right for you, I just love mine.) 

Simple Tricks to Book Cheap Flights

Clear Your Browser History 

This may be a myth, but I was told that when your computer stores your search history, it uses the information against you when you browse for flights. For example, I am searching for a flight on Tuesday, but I’m not really feeling the price. So, I turn on Google Flight notifications and check back next week. When I return to Google Flights the following week, my computer says, “I know you want this flight, so I’m not going to show you that the price decreased. I will instead show you a slightly different, but still very high, price in hopes that you are desperate enough to reserve this inflated load of crap.” 

Perhaps I’m paranoid in believing that my computer and the airlines are in cahoots together, but I lose nothing by clearing my history before searches. In all, clear your search history before attempting to book cheap flights.

Book Tuesday or Wednesday  

Unless it is an absolute emergency, never reserve a flight on the weekend. What are you nuts? Airlines hike up the prices over the weekend because 1. they are thieves, 2. that’s when people are more likely to make drunk and emotional purchases. Don’t do it. If possible, wait until Tuesday or Wednesday. I don’t know the science behind this, but, more often than not, flights are significantly cheaper during the week.

Booking mid-week will save you money. End of story. 

Good luck and I hope this saves you tons! If you enjoyed these tips, share it with a friend and on your favorite social platform!