Secrets of the Skies: An Insider’s Guide to Travel Hacking

Most people don’t usually sit around thinking about miles and points. We do. In fact, we spend just about every minute of every day obsessing about points hacking and working the system to earn so many miles your head would spin. (We even dream about it!) Over the years, we have become experts on the subject. In fact, that's why we started Chatflights: To put our expertise to work and help you use your miles to get a taste of the good life.

Here’s the other thing you should know about us: We love letting our community in on our secrets. Don’t believe us? Keep on reading because we’re going to teach you some of our insider travel hacking tips that will help you rack up more miles and better status — and take you on even more amazing trips. Let’s go.

View miles as an asset

First rule of thumb: When it comes to points and airline miles, you need to be thinking of them like money. Or better yet, treat them like investments or stocks. Keep them and they will eventually pay dividends in the same way.

READ MORE: Learn about the psychology of miles

Hoarding miles is a good thing

There are two schools of thought when it comes to miles. Some people view miles as a way to get cash back on their credit card, whereas other people see them as something more aspirational. For instance, you can save your miles to go on a honeymoon. And the latter people are the ones who will win in the end. First class ticket to Bali, anyone?

But don’t wait too long

Saving and hoarding is good, but be careful, since miles can expire and airlines can also devalue them. In fact, on many airlines, miles expire in three to five years, if you’re not careful. Our advice:

  • Depending on the airline, you shouldn't save miles for more than two years.
  • You should use your miles once a year. We’re not saying you should blow all of your miles on a short-haul tickets. But the more you’re focusing on accumulating miles, the more you’ll be earning, allowing you to take those aspirational trips more often.
  • Use your miles to plan that annual splurge Christmas trip or a spring break vacation. That way, you can make sure that you're not going to lose points.
  • If you have miles that are about to expire, making a small purchase on a shopping portal or signing up for an airline credit card might save the day.

Put those business miles to use

If you're traveling for business, a lot of companies have corporate travel agents. Ask if you can book the trips yourself and put them on your own card and get reimbursed. That's one of the best ways to earn a lot of miles.

Credit card purchases can turn into miles. Photo by Avery Evans on Unsplash.

Use plastic

This goes without saying: Don’t let miles go to waste by using cash. Follow these rules:

  • Put everything on your card. Everything! All those small purchases where you might normally use cash? By putting them on a credit card, they are converted to valuable points, which can add up.
  • Pay your bills with plastic: You'd be surprised how many companies — even utilities — will let you pay your bill with a credit card.
  • Use Plastiq: One of our favorite services is a site called — which lets you pay your bills with a credit card for a small transaction fee of around 2%. And just in case you were wondering: There's usually going to be a positive value even if you’re paying an extra fee.

Refer your friends

Tell your friends to sign up for a card with American Express, which has an excellent referral program — it’s one of the best ways to earn miles quickly. For each person who signs up, you’ll get a bonus of 20,000 to 40,000 miles per referral. We have friends who are very good at referring people to Amex and earn hundreds of thousands of miles per year this way.

Use alliance partners to obtain status

These days, the big U.S. carriers are typically tougher than foreign partner airlines when it comes to getting elite status. For instance, when you fly on United, the airline will look at how many dollars you spent — in addition to the distance flown. But when you use a partner, they will often calculate the miles using an older system or require fewer points. Consider these examples:

  • Aegean Airlines, a Greek regional carrier, makes it possible to obtain Star Alliance gold status by earning just 24,000 miles and flying with them 4 times.
  • British Airways makes it easy to get Oneworld status. So if you’re flying on American Airlines between New York and Los Angeles, you’re better off applying your miles to British Airways’ points program.  
  • Turkish Airlines is another carrier to think about for getting status on Star Alliance.
You don't need to be in the back of the plane. Photo by JC Gellidon on Unsplash.

Don’t assume you can’t fly in Business Class

Sometimes, business class and premium economy are only marginally more expensive than economy — and you’ll get many more miles if you’re in a higher class of service.

Don't ignore your orphan miles

When you have a few miles from taking a small trip on a random carrier — not your loyal airline — those are called orphan miles, and a lot of people let them go to waste. That’s a mistake. In the event that you need to go on a short trip somewhere, they can actually be useful. Here are some examples:

  • British Airways has a program that will charge you based on the distance of the flights. So you might be able to fly from New York to Toronto for only 7,500 miles — which is cheaper than paying for the flight in cash, which will cost $300.
  • Or you could pay to top off the miles.
  • Or use a shopping portal combined with cash plus miles to get to the ticket price. You just need to have vision.

READ MORE: Buying Miles for Travel: Does it Make Sense?

Want to go to the Maldives? There might be a way. Photo by Ishan @seefromthesky on Unsplash.

Open your mind

Airline availability is usually dependent on capacity, so instead of setting your mind on one place, look for hubs or routes where there are a lot of seats for sale. Some things to think about:

  • Dying to go to Tahiti? You might have a hard time getting there with points, since very few airlines fly to the South Pacific.
  • Maldives on your mind? Be flexible with routing. Star Alliance carriers have very few business seats to the Maldives. If you fly via Singapore, there will be more seats.

Go where the flights are

Here are four long-haul dream destinations where you’ll usually find a lot of availability for free flights. Just keep in mind that there are currently some restrictions as to where Americans can travel during the pandemic. But also remember that you can book flights using points and easily cancel the flight or rebook it if there’s an issue traveling to that destination.

  • Australia: You’ll have a lot of options for flights from the U.S.
  • Hong Kong: From Hong Kong, you can get cheap flights to many other areas in Asia, like Bali.
  • Kenya: It’s much easier to get a flight to Nairobi than Johannesburg.
  • Zanzibar: Who wouldn’t want to be lying on a beach on the Spice Island right now?

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