How to Find Cheap Flights Like a Boss!

I’ve had a lot of people ask me how I’ve found cheap flights to fly around the world for a year. Since this is something I wondered myself before leaving on my trip, I decided to create a post (and tutorial video) to show you the secrets I learned to find cheap flights like a boss! Now that I’m not traveling full-time, I use a lot of these tricks to ensure I get the cheapest flights possible.

When planning a trip, flights can be the most expensive part, but when you use some of the strategies below and use the right tools you can have plenty of money left over to actually have a wonderful vacation! Sometimes it’s not that easy and you actually have to work at it while other times great deals can just fall into your lap.

There are many different factors that are dependent on finding cheap flights, but here is the ultimate guide to finding hacks that can help you in the future.

So, how do I find cheap flights? Here’s how it’s done!

How To Find Cheap Flights

1. Use Discounted Airline Sites

I just finished making a video tutorial about how I find my cheap flights here. Using discounted airline sites has been the number one way I find cheap airfare, but it’s important to keep in mind that using multiple sites and trying them all is a better option than only using one all the time.

My go-to sites are Skyscanner, Google Flights, Momondo, and Kayak to find the best prices. I’ll then compare the prices I get on each of these sites to the others to see where I can get the best deal.

The best part about Skyscanner and a few of the other sites (some are just implementing this) is that you can type in your departure location and then put your destination as “Anywhere or Everywhere”. This will then make the search engine look and see where the cheapest places to fly are on the travel dates you’ve specified.

I have a video of how I find my hacks on Skyscanner here. Tip: None of these sites are perfect, so just beware that they all have their flaws.

2. Use Credit Cards & Follow the Points and Miles Gurus

This is a big one. Many people are afraid of credit cards, but you really can use them to your advantage when finding flight deals if you’re smart about it. I literally put every single thing I ever buy on my credit card. As of now, I use the Chase Sapphire Reserve card and am slowly starting to figure out the points and miles business by following sites like The Points Guy and The Frugal Travel Guy to find the best deals with credit card points. Before the Chase Sapphire Reserve (my favorite card of all time) I used the Chase Sapphire Preferred which was a great entry-level to points card.

There is an entire industry dedicated to points and miles hacks and there are so many ways to use credit cards to your advantage.

A few things that work for me when using credit cards is purchasing regular day-to-day items on the credit card websites instead of the actual websites themselves. For example, if I want to purchase something from Target, I can log in to Target via the credit card website, and then I will get double the points shopping from the portal.

I also use my card for all travel-related expenses because I get more points per $1 spent on travel purchases and at restaurants.

Each credit card is different, but there are small ways you can gain airline points by just changing up the way you’re purchasing things you already buy each day. Credit cards have helped me get A LOT of free flights and points over the years. It will save you money in the long run, I promise! Like I said earlier, I put almost every purchase I can on my credit card and just pay it off immediately.

3. Keep Your Searches Private

This may sound like a weird one, but if you can keep your searches private when you’re looking on all of these discounted flight sites that would probably be a good idea.

I don’t think this happens all the time, but the sites can track what you’ve searched for and raise their prices. Just like your search engines know what ads to serve up to you, the airlines are tracking what your computer searches for. Then they can raise the price of that particular destination if you keep coming back for the same thing.

Make it a habit to search for flights in an incognito window just to be safe!

4. Set Up Alerts and Flight Hacker Emails

I LOVE setting up flight alerts and signing up for flight hacker emails. This has been the source of some of the best flight deals I’ve ever gotten. I first will recommend signing up for Secret Flying’s daily email because they find airline errors and mistake fares and send them out as soon as they find them. Scott’s Cheap Flights is another great email to sign up for to get deals to your inbox.

For each of these, you can pick your departure location and then get those locations sent to your inbox. At the end of this video tutorial, I show you a bit about Secret Flying’s emails. Here are some other great sites to keep an eye on and set up alerts with Airfarewatchdog, The Flight Deal, Holiday Pirates to get cheap airline tickets.

Setting up fare alerts is also a great way to get notified on specific flights you may want to take. This is especially great if you know exactly the dates you want to leave. I recommend using Kayak or Google Flights and you’ll get a notification when your airfare drops.

5. Fly Into Larger Airports

This tip is hit or miss, but if you want to fly the cheapest way possible then you’ll usually want to fly in or out of a larger airport. Smaller airports always cost more money because the smaller flights have to connect to them.

So, when booking flights—if you can—try booking into the larger hubs and taking some sort of ground transportation or car rental to your destination. Sometimes taking ground transfers/renting a car can actually cost more though, so make sure it costs less than just taking that extra flight.

6. Be Flexible

This is the key to getting the cheapest price on your flights possible. If you’re flexible on dates, locations, and times then you’re good to go. I realize most people don’t have this much flexibility in their schedules. However, just know if your destination or departure location is flexible and you can leave on a random day during the week instead of a Friday night, your flight tickets will probably be cheaper!

7. Book Your Flights on a Monday – Wednesday

Airlines won’t necessarily confirm this, but the best flight deals are hands down on these three days. I’m not saying you can’t find them on other days (you definitely can). However, in my experience, when you search for cheap flights, try it on these three days. I’ve done a few tests and flights typically will go up on Thursday and over the weekend.

8. Don’t Always Take Direct Flights

It helps to be flexible when flying, but this one is sometimes worthwhile. Let’s say you find a flight direct to NYC, but then you find a one-leg flight to Denver with an even cheaper flight to NYC than the direct.

If you can be flexible and have the time, flying a few legs per flight can sometimes be cheaper than just booking a direct flight. Sometimes this is worth it and sometimes it’s not. I found a direct flight from Berlin to Athens as my final destination but found out there was a stop in Kyiv (totally out of the way). It meant my flight was cheaper and I saved over $200 that way. If you have the time and think it’s worth it then try it!

9. Look Last Minute

If you’re flexible, then it will help to look last minute for flights because airlines will want to fill up their aircraft and will typically lower their prices if they have a lot of spots left. I don’t recommend waiting until the last minute all the time, but if you ‘wanna getaway’ to a random spot, this is a good idea to use one of the searches to “anywhere” on the flight sites (like I did here) to find the cheapest deals.

10. Book Ahead, But Not Too Far Ahead

Yes, I know I just said to look last minute, but booking ahead of time is also a good idea. I typically recommend looking 6-8 weeks before your flight OR 3-ish months if you’re booking in high season to a popular destination or going on an international flight.

11. Sign Up for Frequent Flyer Miles Programs

First of all, I recommend becoming an awards member on all airlines you fly on. While I was working full time and traveling a lot I would sign up for an airline’s frequent flyer program whenever I took my first flight with them.

I currently have a number for all of the airlines that I’ve flown in the USA and abroad and continuously make sure they are updated each time I take a domestic flight. If you don’t fly that much yet, that’s okay, just start signing up when you fly with those airlines. These mileage points add up and can usually be combined with credit card points to get you great deals!

12. Combine Credit Card Points with Frequent Flyer Miles

Did you know that many credit cards have partnerships with airlines? You can now rack up points on specific airlines and then transfer them over to your credit card to double your points! I recommend doing some research on what airlines your credit card partners with because this is a great way to get the most out of your miles!

13. Fly Budget Airlines

There are tons of budget airlines out there that offer fewer “perks” and are typically much cheaper. For example, Allegiant Airlines will typically only fly on specific days, but their prices are much lower than other airlines. Southwest is another budget airline and has great options if you “wanna get away”.

Just know that some of these budget airlines will try to nickel and dime you. This is just how these budget airlines survive. So by charging you to bring a carry-on bag, charging you to pick a seat, not serving food onboard, or charging you to print the ticket all can affect the price. It will be a good idea to compare the price with a regular airline before you hit book to see if the risk is worth the reward.

Some common budget airlines in the U.S.

Try Booking a Flight Now on Skyscanner!

I know there are a lot of you out there with more great flight hacking tips! What did I miss? Any other great advice?

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3 Comments

Liana February 22, 2018 at 10:05 am - Reply
Awesome tips! Especially love the info about using credit cards for daily purchases. I also buy everything possible with credit cards to rack up as many points as I can (but of course pay them off each month😉) My current card lets me use points for anything that’s coded as “travel” so it’s super flexible. Also, great to know about the booking timeframe window of under 3 months. Thanks so much for the great advice!
- The Traveling Spud March 4, 2018 at 11:31 am - Reply
  YES! It’s so smart to use credit cards. I wish I used them more often!
farenexus September 10, 2018 at 4:05 am - Reply
Nice article.