How to Find Cheap Flights

So you know that booking flights in advance will usually get you a better deal. You’ve probably also bookmarked a handful of websites where you can compare different airfare prices and hopefully snag the best deal. So let’s get a bit beyond the obvious basics here. First, it’s important to understand how airlines work, so you can get an idea how you can work this information to your advantage.

Why Flights are Cheaper if Booked in Advance

The reason behind this is that airlines don’t find the idea of a mass of people trying to book flights at the last minute all that appealing. Airlines need to plan ahead of time how much space for baggage will be needed for the flight as well as the amount of food they’ll have to carry. This is difficult for them when the flight is fairly empty until the date of departure nears. Fair enough, right? Something else to keep in mind is that a lot of people who book their flights at the last minute are usually on business trips (which means, more often than not, the business is paying for the flight).

Big businesses can generally afford the prices that a last minute flight calls for. I highly suggest not booking a flight any later than a week in advance for these very reasons. Sometimes you might get lucky, (I certainly have), but it’s best to leave some room. Better yet, book with an airline that offers price guarantees. This means there’s a chance for a refund of the difference between what you booked and what you later found. A few airlines known to offer this are, Virgin, British Airways, EasyJet, and RyanAir. Make sure you read their fine print and verify these offers still stand!! 

Hours to Book your Flight

It’s best not to book your flight between 9am and 5pm for domestic flights. The reason for this is that these are usually business trip times. (Again, meaning you are willing to spend more.) Leisure travelers or people flying for personal reasons, are more flexible and are more willing to fly at an inconvenient time for a very convenient price. The trick is to fly when everyone else won’t or can’t. Those are the emptier flights that are trying to be filled by providing a cheaper cost to you. Just know, the more inconvenient a flight is to you, the cheaper your cost will be. (Same goes for Non-stop vs. Connecting flights.)

The trick is to fly when everyone else won’t or can’t.

Also, be sure you understand the difference between “direct” and “non-stop” flights. Although these sound the same, the difference is, that a direct flight has more chance for delays because it can touch down at another city on the way to it’s destination. So if you want less chance of delays, go with a non-stop. (Remember, back to inconvenience: a flight with connections will usually be a lot less than a non-stop flight.)

Airlines generally update their systems around midnight to 1am on a Wednesday night. (Though there are some airlines update around the evening on a Tuesday.) You’re likely to snag a good deal at this time because the flights are new and haven’t had time to be in demand yet. Be sure you are going by the time zone of where the airline you will be booking with is located!

Cheapest Days to Fly

The cheapest days to fly domestic are Tuesdays and Wednesdays. Flying on a weekend will almost guarantee you a higher price on your airfare. Business travelers are more likely to fly on a Monday and leave before the weekend. If possible, try to avoid flying on weekends, Mondays, and Fridays. Always shoot for mid-week. Momondo has an excellent chart of the cheapest days to fly and allows you to adjust your dates seamlessly:

Flights are also generally a lot cheaper right after a holiday. An old friend told me he was able to book a roundtrip flight from LAX to Dublin, Ireland for under $500 the day after St. Patrick’s Day. Flights like these aren’t uncommon after special holidays. Some of the cheapest days to fly are in early January, right after the holidays. May is also a good time to fly if you want a pleasant summer vacation without the summer prices, the summer heat, and those sweaty tourist crowds that start in June. Also keep in mind the season and events that are taking place where you are planning to fly to. Looking for that sweet spot in the off season where weather is still pleasant is always a good idea!

Error Fares

Error fares are simply that; errors. These are ridiculously low deals (think: LAX to Hawaii for $7 roundtrip!!!) that happen due to currency conversion mishaps, computer glitches, fuel surcharges not being counted, or just plain ole human mistakes. News travels pretty fast when these things occur so it’s important to jump on these immediately when you hear about them. One site worth noting is Secret Flying. They scour flights looking for pricing errors and have been known to find some pretty crazy ones like the one I just mentioned in 2013.


Don’t exclude the valuable information you can get from merely talking to other travelers. Besides reaching out to friends and family for travel secrets, why not also join a forum? Mileage Run on FlyerTalk is a good place to start. There you’ll find a place to ask about and share unique tips to maximize your miles/points.

Refunds and Booking directly with Airlines

Earlier, I mentioned that some airlines are willing to refund you the difference should you find a cheaper ticket. This only works if you keep an eye out for price drops after your purchase! Most people don’t check back on prices after they have already bought a ticket. Even fewer people call the airline for a refund for the difference. Take advantage of this. A good site that can help you keep track of price changes on your flight is, Yapta.

Keep an eye on price drops even after you’ve already purchased your ticket.

I also want to point out that this is much more possible if you booked with the airline directly. Airline sites are usually scoffed at by bargain hunters, but don’t disclude them in your research! A good checklist to follow is to first check with your favorite flight aggregators, then once you’ve found a flight you’re happy with, check with that airlines site and try to look for that same flight. You’ll occasionally find it cheaper there. It’s worth checking!

Hidden Cities

If you’ve ever been trying to get to New Orleans from LAX for $300, only to find a flight to Atlanta, GA with a stop in New Orleans for $200, this was not a coincidence. Airlines mainly price their airfare on the market. You can always buy the cheaper ticket to Georgia, and simply hop off in New Orleans. This is called a Hidden City Fare. This is not illegal. However, some consider this to be unethical. Not to mention, airlines frown upon this and will sometimes cancel the remainder of your full trip, leaving you to buy a one way ticket home when you want to return. That’s really rare, but it’s been known to happen. Make sure you plan this out carefully if you choose to do this.

Graphic from

A great website to find hidden city fares is, SkipLagged. Yes, the site that 22 year old genius created to find you some insanely low flight deals and got sued by United Airlines. (He won and raised a ton in legal fees.) Again, hidden cities can sometimes save you a ton of cash, but please plan accordingly. This works better with one way travel. I also hate to have to point out the obvious, but don’t check in any bags. Your bags aren’t savvy to your schemes and will continue the trip without you! If you found an insanely good hidden city deal and absolutely must get more luggage over to your destination, then consider shipping your stuff. Luggage Forward is a good service and does price matching to guarantee you the best possible shipping costs. 

Free First Class Upgrade

Unfortunately, we are no longer in the golden age of free first class bumps. Nowadays, you’re considered very lucky (or possibly famous?) if you get bumped without a fee. There are still a few ways you can help your cause though. A good way to go about asking for an upgrade is to fly on an overbooked flight with an underbooked first class. If you have a reservation on the flight already, they will usually prefer to upgrade you and let on a standby. Also, be sure you are on their frequent flyer program.  An underbooked first class and is rare nowadays, however. As is special treatment for being a frequent flyer. So make sure to have some backups to help your cause:

  • Get a co-branded credit card with your favorite airline. Alaska Airlines Visa SignatureAmex Delta Reserve, and United Mileage Plus Explorer are some good ones to have.
  • Arrive very early, when agents aren’t swamped with people demanding attention. Ask politely if they could please consider you should they be doing any upgrades on this flight.
  • Being courteous and dress professionally. Looking the part still applies.
  • Stay informed! Use a service like Expert Flyer to get seat alerts. This site is absolutely invaluable. The pro subscription is totally worth it, but there’s a free option as well if you want to give it a spin.

If You Are a Student

Check out Student Universe and STA Travel for deals on student fares. If you’re attending college or university in Hawaii, consider checking out Island Air’s student program for travel within the islands. There are also travel scholarships you can apply for. A good one to note is Student Youth Travel Association. Also, don’t forget to get an International Student ID to save while traveling.

Make sure to subscribe to the following so you don’t miss good deals:

Airfare Watchdog – Alerts you when there’s a drop in fares for your chosen trip.

Hopper – This app let’s you know when’s the best time to fly.

Travel Zoo – For bargain travel packages. Sign up for their newsletter to be alerted about sales and error fares.


That’s all for now. I’ll be adding more in future posts. 🙂

Happy Exploring!