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Travel Hacking: Take 1+ Free Flights Every Year (Autopilot Plan)

Travel Hacking

Do you take a round trip flight every year, for free?

If not, you’re missing out.

Thanks to the ubiquity of frequent flyer programs, rewards networks, and credit card promotions, it’s easier than ever to set yourself up to earn a free trip annually.

And most people are able to earn two free round trip flights each year.

So why aren’t you already doing this?

Probably because there are a hundred and one ways to go about it — it’s a confusing mess.

From credit card offers, to linking your cards to dining programs, to airline promotions… there’s a whole world of hoops to jump through if that’s what you’re into.

However, this is not a post about every way to earn miles and points.

If you want to earn every single point possible (even if that means spending 2+ hours/week on promotions), go check out The Points Guy.

If you want to set up a “one and done” plan that will earn you at least one free round trip flight every year — without you having to jump through lots of hoops or doing tedious work — read on.

This is your Travel Hacking Autopilot Plan.

It’ll earn you the most amount of free trips for the least amount of effort.

We’re going to leverage Pareto’s 80/20 rule: 80% of the results with 20% of the effort.

Remember that this is a “set it and forget it” plan, you’re going to invest a little time now in travel hacking to reap the rewards for a lifetime.

Your Autopilot Plan could translate into 70+ free trips if you follow each of these steps.

Approximate time to set up your plan: 60 minutes

How to Set Up Your Travel Hacking Autopilot Plan

Step #1: Sign up for a frequent flyer program with one airline from each airline alliance.

There are three airline alliances worldwide:

Each alliance has a number of partner airlines that work with each other.

The key benefit of these alliances? You can use frequent flyer miles you earn on one airline to book travel with a partner airline.

They just need to be in the same alliance.

You want to have a membership with at least one airline from each alliance so that you can transfer your miles around to get you the best (lowest mile requirement) flight deals.

More on that in Step #4.

So which airline frequent flyer programs should you sign up for?

Unless if you have a specific preference, sign up for the frequent flyer programs from the following airlines:

Pro-tip: Focus on earning miles on one airline per alliance rather than spreading miles around thinly. You can’t combine miles from multiple airlines in one transaction, so it’s better to have a bunch of miles with one airline in an alliance than a handful of miles on a few airlines in the same alliance.

Step #2: Use a rewards credit card to multiply your miles.

You don’t have to spend more money to take advantage of travel hacking, but whatever money you do spend should be spent with a travel friendly rewards card.

Right now, the two best credit cards for travel are:

  1. The Chase Sapphire Preferred Card, and
  2. The American Express Starwood Preferred Guest Card

Note: I’m not using affiliate links here. If you sign up for these cards, I do not make any money. The only reason I’m linking to these card programs is because they are simply the best options for travel hacking.

Both of these cards come with no foreign transaction fees, allow you to transfer points to miles, and come with sweet bonus points for spending a certain amount within the first few months.

If you sign up with the Chase Sapphire Preferred card, you’ll earn 50,000 points by spending $4,000 on the card within 3 months. Plus you get an extra 5,000 points if you add an authorized user who makes a transaction within the 3 month period.

If you sign up with the American Express SPG card, you’ll earn 25,000 points by spending $3,000 on the card within 3 months.

Both cards will give you 1 point per dollar spent.

With the SPG card you get 5X points for spending at Starwood properties (they have a ton of hotels and resorts in the program like Westin, St Regus, Sheraton, Four Points, etc.).

With the Sapphire card you get 2X points for spending on travel and dining.

Whether you sign up for one card or both, remember that you do not need to suddenly start spending a ton of money on your cards.

Just spend enough to get the beginning bonus, and then enjoy the sweet perks and consistent point accumulation as you spend money with your card(s) over time.

Step #3: Tap into rewards networks to earn miles on an ongoing basis.

Whether you’re going out for dinner, booking a hotel room, or ordering stuff online, you can earn free miles for doing the same things you would have done otherwise.


Link your credit cards to dining programs to earn points when eating at select restaurants.

You can link as many cards as you want to a dining program, but you can only have one card associated with one program (so you can’t link the same credit card to multiple programs).

Even if you don’t look up the list of participating restaurants for a dining program, when you happen to dine at one of them you’ll get bonus miles, just for doing what you were going to do anyway.


If you need to book a hotel, do it through Rocketmiles.

You’ll find plenty of hotel options at different rates, and you’ll earn miles for your stay.

For example, you could earn 2,000 miles on American Airlines by staying 2 nights at Hotel Nexus (in Seattle) for $143/night.

Earn free miles

The prices and points earned vary significantly, so take a few minutes to find a good deal. I found a hotel that paid out 4,000 miles for 2 nights at $119/night, but it was further away from the downtown area.


Check out evreward before you click that buy button.

Evreward will tell you what points/miles you could earn by purchasing a product from an airline’s online mall.

Again, focus on buying the things you normally would, but now you can go through the evreward link to an airline’s online shopping mall where you’ll earn bonus miles for your purchase.

You can find hundreds of other ways to earn points by searching online, but again, we’re going for simplicity and getting the most amount of points for the least amount of effort, so we’ll call it good on the earning front for now.

Step #4: Redeem your points and miles for free flights.

OK great, now on to the fun part.

The previous steps positioned you to consistently load up on points (on your credit card programs) and miles (on your airline frequent flyer programs).

Now it’s time to take those points and miles and travel the world for free.

Say you have 40,000 miles on United’s frequent flyer program (UnitedMileage Plus).

You’d need to earn another 35,000 miles for a total of 75,000 before you could take a free round trip flight to the Caribbean in economy.


You could book your round trip flight to the Caribbean with one of United’s partner airlines for only 35,000 miles… leaving you with 5,000 miles left over in your account.

When redeeming miles for free flights (called “award tickets”), always check an alliance or partner awards chart to see the mile cost by region.

Using your miles on a partner airline is almost always the better way to go.

Here are some handy resources:

Delta is a little trickier since they took their partner award chart off the web, but you can still go to their book a flight page and choose to book your travel with miles and make sure the “Delta & Partner Airlines” box is checked.

And remember that while you are technically dealing with two different currencies — points and miles — your points can be redeemed for miles, usually on a 1:1 basis.

Also, try to only redeem your miles for expensive flights.

If the flight is cheap, it’s almost always better to buy the flight.

Divide the cost of the flight by the number of miles you’d have to use to get the flight to find the value per mile for a given flight. If the value of your miles on that flight is less than 4 cents/mile, it’s probably best to just buy the ticket and save your miles.

Pro-tip: The Amex SPG card gives you a bonus 5,000 miles for every 20,000 points you transfer to airline miles. That means your 40,000 points are worth 60,000 miles (with the exception of United – see full transfer details here).

So get to it and start traveling for free!

If you’re like the average American and spend roughly $53,000 per year (or $4,416/month), then you’ll be racking up points and miles in no time.

And if you’re low on cash and could stand to make some extra money, check out my post on remote jobs.

I’ll leave you with the words of Mark Twain:

“Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one’s lifetime.”

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