Cheap flights and travel hacking Matt Wilson

Regional flights can be a lot of fun. I scored this seat on Cape Air to Nantucket…

Finding cheap flights is a science.  As the co-founder of a travel company, we bring our team all over the world, and try to do it as wisely as possible.  We take travel hacking very seriously.  The more money we save on flights, the more money left to spend on incredible experiences.

Here are ten awesome travel hacks to help you find cheap airfare:

First off:

Expedia has a best price guarantee.  If you find something cheaper anywhere else, Expedia will match it AND give you $50.  So I’ll let it be known upfront that we’ll be using Expedia.  Our goal now is to beat Expedia…

1) Book during the right time of the month

If you are booking on your credit card, you should be paying attention to your cashflow.  My billing cycle turns over on the 28th of every month, so you’ll almost always find me booking flights after that day.  Through American Express, I will have nearly two months to pay that off…

I just booked my flight for our Under30Experiences April 2-6 trip to Costa Rica.  Luckily for me, March’s bill will come to me at the beginning of April, and I’ll have until the end of April to pay it.  Pretty sweet.

2) Book during the right time of the week

By looking at historical data and watching trends over the last several years, you’ll notice that sitting down to book flights in the middle of the week, Tuesday – Thursday is most economical. did a study here and said Wednesday at 3PM ET is the best time to book flights.

3) Find off-peak flights

Most people need to fly home on Sunday afternoon to get back to work on Monday.  But if you have more flexibility, why not fly home off-peak hours?  Nobody wants to fly on Saturday night, or on red-eyes, or super early in the AM.  Be sure to use the +/- 3 days button on to see what day is cheapest, and you can save a fortune.

4) Search other destinations and buy a connecting flight

Flying to Asia or Europe?  This works really well.  If you are flying to Bali, first research flights that fly in to the Bali’s DPS airport.  Then, compare those prices with flying to other cities like Hong Kong, Singapore, and Shanghai. These major hubs are going to be way cheaper, so, search a local carrier like AirAsia to get you the rest of the way there.

For our U30X trip to Bali, I found JFK to Taipei nonstop for $1000, and then TPE to Bali for $300.  Even more fun I’ll get to check out Taipei for however long I want… remember… it’s all about the experience!

Superhack: Search your flight to Bali, and then see through what airports the cheapest flights connect in.  This is how I found Taipei– not a city in Asia I would ever thought to fly into, but it’s where most of the cheap flights were stopping. I’ll buy a second ticket and get my to Bali for less.

5) Take advantage of free-stopovers

A lot of the cheapest flights are the ones most people consider the worst–with long layovers.  This mindset is for people who simply aren’t good at life.

Last year, I found myself flying Emirates Air (amazing) with a long layover in Dubai.  I called the airlines, and arranged an even longer, 24 hour stopover, and had a blast.  I rode camels in the desert, swam in the Persian Gulf, saw the Burj Khalifa, Palm Islands, indoor skiing, and had dinner with a friend from college.  Not a bad day.

Icelandair offers up to seven days free stopover if you connect in Reykjavik.  Flying to Europe this year? Book your flight on Icelandair, and go spend the day relaxing in the Blue Lagoon. It’s natural beauty will blow your mind, and it’s very close to the airport.

6) Watch the price predictors

Many sites including Kayak and Bing Travel use data from past flights to predict the prices of upcoming airfare. For flights to places that are undiscovered like Nicaragua, we always notice that the price predictors say to wait.  It’s not uncommon for flights to go to Managua only half full, and get cheaper as time goes on.

Keep an eye out, because on any given day flights can jump up if it gets too close.  I recently couldn’t get on a flight from Miami to Managua, because our attendees bought up all the flights.  I had to pay a lot more on another airline and travel alone.

7)  Buy travel insurance ASAP

This one sounds obvious but you need to protect yourself against flight cancellations, or unforseen circumstances.  We suggest World Nomads Travel Insurance to protect yourself against trip cancellation, if you or a business partner get sick, a relative dies, or your trip gets interrupted because of inclement weather.  This might not save you money off your flight, but it’ll save your ass in an emergency.

8) Find the right credit card for you

My life and business is devoted to travel, so I choose to pay for an expensive charge card with American Express Platinum. This isn’t an article about selecting credit cards, but yes, I did get 30,000 miles just for signing up… Find mileage bonuses on a low APR credit card theoretically will let you travel with no money down for a year or two… Be careful here.

9) Know your frequent flier alliances

Mainly, be sure you are signed up with one of the big three airline frequent flier groups, Star Alliance (United, US Airways, Copa, Luthfansa, SWISS, EVA Air)One World (American, British, Cathay Pacific, Iberia, LAN, Qatar), and the new Sky Team (Delta, KLM, Aero Mexico, Air France, China Airlines…)

Try to book with them, even if they are a little more expensive. You’ll make up for it in the long run with free flights.

I prefer Delta because when I book via American Express Travel I get triple points. Yup. Double points for every travel dollar I spend with AMEX, and then the frequent flier miles with Delta on top of that. You get this deal with any airline on AMEX, but the nice thing with the Delta / AMEX partnership is that you can transfer your points between the two programs.

10) Know your booking sites

With Kayak they let you compare to the big guys like Orbitz, Expedia,, etc… but don’t forget about the other sites like CheapOair, Airfarewatchdog, Skyscanner, and Google Flights. Of course, you should always check the airline’s website directly, and local regional carriers.

11) Setup price alerts

You’ll be able to setup fare alerts on a lot of these sites, and they’ll notify you via email of any price change. You want to watch the flights for a little while, but in general, the earlier you book the better. You’ll be able to wait until the right time of the week or month (as mentioned in tips #1 and #2), but don’t wait too long or you’ll miss out. Price predictors (as mentioned in tip #6) rarely say they flights are going to come down in price.

Superhack: Put it all together. Here’s my general process when booking flights:

Search Kayak for the flight you want, and check the price predictor.  If the flight is more than 3-4 months away, I’ll set a fare alert, and watch the price. On a Tuesday or Wednesday, at the beginning of the month, after my credit card is on a fresh billing cycle, I’ll check the flight on the search engines again, and then head over to American Express Travel where I can pay with as many points as I have, bringing down the fare, and put the rest on my card.

Happy savings… and when you do, be sure to get that $50 from Expedia!

Matt Wilson is co-founder of Under30CEO and Adventurer in Residence at the travel company Under30Experiences.  Read his free e-book The Escape Manual, the secret to temporarily escaping your job, living a life that makes your friends jealous and making memories that last a lifetime.