Last Updated: 10/10/19 | October 10th, 2019

Last month, my friend Pat Flynn came to me with a problem: he wanted to fly Cathay Pacific business class round-trip from the US to a conference in the Philippines. He had only a few frequent flyer miles and was all like “travel hacking, what?”

For those of you who aren’t familiar with the term, travel hacking is the technique of legally collecting loyalty points for travel programs and then gaming said programs to get free or severely discounted travel.

Long story short, Pat needed help getting the miles needed for the flight.

In the words of Barney Stinson: “Challenge accepted!”

I had two months to get Pat the 110,000 miles he needed.

I’ve written about traveling business class for free before, but as with everything in travel, methods and tricks that worked in the past might not work now, especially when it comes to airlines. They change their rules all the time.

As you may already know, I am an avid travel hacker because I hate flying coach. To me, there is nothing worse than being in coach on a 10-hour flight — and if I can avoid it, I will. When you are up in the air as much as I am, you want comfort.

So I collect points in order to upgrade or redeem for business- and first-class tickets, have a lie-flat bed, and enjoy some luxury before staying in my $10 a night dorm room. (Yes, I’m a bundle of contradictions. I’m a Gemini.)

Pat was a great test subject and let me take the reins. Here is how I made things happen for Pat:

Since Cathay is part of the Oneworld Alliance, their U.S. partner is American Airlines so we worked on getting him American AAdvantage miles.

Pat has great credit and has a lot of business spend so it was easy for him to get the cards he needed. (Don’t worry. I write later on what to do when you don’t have a business!)

First, Pat signed up for an American Airlines Citi card, which offered a 30,000-point sign-up bonus when he spent $1,000 USD in 90 days.

Second, he signed up for the business version of the same card with the same deal. (Note: You don’t need to be a business to get a business card. I used to sign up for these cards as a sole proprietor before I incorporated. Credit card companies don’t care.)

Third, I made him open a Starwood American Express card, which offers 25,000 Starwood points when you spend $5,000 USD in 90 days. He then transferred those points to American Airlines. Since Starwood gives you a 20% transfer bonus on 20,000 points, he got 35,000 points (30,000 from the bonus, 5,000 from the spending) to his AAdvantage account.

After it was all said and done, Pat had 97,000 frequent flier miles.

But how to get those last 13,000 miles? There were a couple of ways he could do this:

Pat could have “faked” his spending (which he also could have done to meet the spending requirements). He could have sent $1,000 every month via Amazon Payments to his wife without any fees and then she could have cashed the money back into their bank account. (This is often called “manufactured spending.”)

Or he could have walked into a CVS and bought pre-paid credit cards with his credit cards, and used them to get money orders, and then used those to pay off his credit card balance.

He also could have used online shopping portals to earn 3-4 miles per dollar spent (Christmas is coming!), meaning instead of spending $13,000 USD, he would have had to spend only $3,200-4,300 USD.

In the end, Pat used his business expenses as well as online shopping to get those final miles (he told me he found faking the minimum spending just too time-consuming and he had other things to do).

Within a month, Pat had 110,000 miles he needed and I converted someone else to travel hacking (score!!!). (He’s already set out to earn miles for a family trip to Hawaii!)

Travel Hacking? Too Good to Be True?

Now, you are probably thinking, “That sounds great, Matt, but I don’t want to open three credit cards nor can I spend that much money! Is there another way?”

Good question! What if you don’t want to open three credit cards?

What can you do that doesn’t rely so heavily on credit cards?

I’ll tell you.

But first: you should open at least one rewards credit card because they are the best way to jump-start your balance. Those big sign up bonuses guarantees you at least a couple of free flights. I mean you can find them up to 100,000 points sometimes!

And, if you’re going to put money a card, you might as well get points for it. I mean, I bet you already have at least one card, right? Why not get free trips from it? Use your everyday spending to gain points for travel, even if you aren’t traveling until next year!

A credit card is a vehicle that prints miles. It’s a miles printing press. Money is spent, miles come out.

So you will need at least one card.

Here are some of the current best card deals out there:

  • Chase Sapphire Preferred (offering a 60,000 point sign-up offer)
  • Hilton Honors American Express (offering a 130,000 point sign-up offer as well as a free hotel night)
  • United Explorer Business (offering up to 100,000 points as a sign-up offer)

For more awesome card deals, you can check out this comprehensive list of my personal favorites.

How to Gain Points with Spending More

After you get a card, here are ways to meet the minimum spending as well as earn a ton of points without spending extra money!

1. Use Your Everyday Spending

If you already have a credit card with rewards, the first thing you should do is put everything on that card. Every dollar spent not using your card is a point lost. I never pay cash unless I have to. If you spend $3,000 USD each month ($36,000 USD annually), that adds up to 36,000 redeemable points (at one point per dollar) earned each year without doing anything extra.

But certain cards have what are known as category bonuses, where you get 2–6 points per dollar spent. It varies by card, but, generally, you get 2-3 points on restaurants, 2–3 on airfare, and 5 on office supplies.

Why get one point at a time when you can get five?

Note: Be sure to check your card’s offers for the latest bonus structure, as cards change all the time. If you aren’t from the United States, be sure to see what cards in your country offer bonuses. There’s always something!

The trick here is to make sure you are maximizing your spending so you always get as many points as you can. For example, I buy gift cards from Office Depot with my Chase Ink business card to get five points per dollar spent (because it’s counted as an office supply) for my day-to-day business spending. I use my Premier Rewards Gold Card from American Express card for all airline purchases, since it offers three points for every dollar spent. (If you have the Amex Platinum card, you’ll get 5x points on bookings!)

Dining out? I use that card too because you get 4x points on dining out (the highest there is).

Grocery shopping? That’s my American Express EveryDay Preferred (those points get combined with the Premier Rewards Gold card because they are both Amex cards).

Paying my phone bill? That’s my Ink card since it’s 5x points!

As Ryan Bingham said in the movie Up in the Air, “I don’t do anything unless it benefits my points balance.”

That’s how you should think about spending too. Don’t ever waste a chance to get multiple points per dollar spent. That way each dollar you spend is maximized for the most points possible.

You want to maximize all your spending categories. Figure out what cards match your spending and then write out a little cheat sheet that lists what cards you should you use for what spending and carry it with you so you always remember to maximize your points!

A word of caution: Use the cards that maximize your points but also are part of programs you want points in! Don’t spread yourself too thin. If you’re using five credit cards for five different programs, it’s going to take a lot longer to bank enough points for free travel.

Here is a list of my favorite cards that offer the best points bonuses!.

2. Use Airline Shopping Portals

All airlines, hotels, and travel brands partner with preferred merchants. These companies—ranging from clothing retailers to sporting good stores to office supply businesses and everything in between—are featured on airlines’ special shopping malls (portals). I never shop in a brick-and-mortar store (though I often go in to try clothes on and then buy the stuff online so I get my multiple miles). By ordering online through an airline’s shopping portal, you can earn multiple miles per dollar spent in addition to any miles/points you get from the credit card itself.

For example, I once registered for Netflix through American Airlines’ shopping portal because it gave me an additional 5,000 miles American Airlines. I went to Target through Chase’s online shopping mall and gained three extra points per dollar spent. I did my shopping for my apartment online with K-Mart via American Airlines’ portal and received nine American Airline miles for every dollar spent. (Note: It does not matter what credit card you use on the portals. You get the miles into your account no matter what. Plus, you then get the points on your credit card so it’s a double win!)

For example, you want new clothes from the Gap? Going into the Gap store gets you one point per $1 USD spent since credit cards don’t offer bonuses for shopping. But, by using Evreward, you see that by going to the United shopping portal, signing in, clicking the link to Gap, and purchasing online you can get three United points per dollar spent. Suddenly, you get 300 extra United points instead of just 100 credit card points for your $100 USD shopping spree! That’s a total of 400 points!

And that’s why these online portals come in so handy—you can increase your point earning on everyday spending much more quickly than if you just walked into a retailer.

Signing up for these portals are easy. Simply go to the website, sign up with your existing frequent flier number, and go shopping. You’ll need to ensure you have cookies enabled on your web browser so they can track the sales. But, other than that, points are automatically tracked and added into your frequent flier account (they take about 6–8 weeks to post).

You can use Evreward or Cashback Monitor to discover the current best deals across various programs. Simply type in the merchant or product you want, and it will compile a list of bonuses the various point programs are offering at that moment.

3. Use Your Family

If you have family, use them to help earn points and meet minimum spending requirements. For example, my parents might fly once a year. My sister, maybe twice. They don’t really need or use their miles, so I have them give them to me (with the understanding that if they ever do need points, I’ll be there to help out!).

My parents use my credit card to purchase all their tickets, and when they fly, they transfer their miles over to my account. So, after they visited Israel, the miles they both earned ended up in my American Airlines account. There is a small fee for the transfer, but it’s worth the extra miles.

Moreover, family members are a great way to help you meet the minimum spending requirements. Get a second card (authorized users on your accounts) for a family member and have them spend away on it (providing you trust them to give you the money to pay you back). I was still in school when I started earning points for my first trip, so my mother put our family’s groceries on my credit card. I got triple points and my free flight to Europe faster than if I did it alone! If you have the ability to do this, do so!

If you don’t trust someone enough to give them a credit card to your account, help them out with a big purchase. Is your sister buying a new computer? Great. Go to the store with her and use your credit card to buy it. Then have her write you a check, give you cash, or Venmo you that day for the price of the computer. I suggest doing this for any big purchases people are you are making (airline tickets, TVs, electronics, etc.).

4. Sign Up For Newsletters 

I sign up for all of the airline and credit card email newsletters so I can stay updated on special fares, deals, and offers. Many of the best deals in the business are only sent via newsletter, and if you don’t sign up, you’ll never know about them. I once got triple miles for three months on my Citi/AAdvantage Executive World Elite Mastercard through an alert sent to me via email.

Moreover, many airlines offer special card sign-up bonuses to subscribers that aren’t available to the public. Be sure to sign up for every airline newsletter!

The following websites are also good resources to find out about these kinds of mileage deals:

  • The Flight Deal
  • FlyerTalk
  • Holiday Pirates
  • View from the Wing
  • Scott’s Cheap Flights (Read my interview with Scott here)

Sign up for deal alerts from them. These deals could be a cheap flight, or points for filling out a survey (see below), playing a stupid game, or liking a company on Facebook. Additionally, many brands offer bonus points when you sign up for Netflix, open a new bank account (I often open accounts just to get the points and then close them), switch cable providers, join a gym, etc. Or you could sign up for fraud monitoring to get points and then cancel it. You can sign up for double miles on certain airline routes, for using a company’s app, or for staying at a hotel on a Friday. It can be anything.

And, even if you don’t think you’ll use the deals, sign up anyway. It doesn’t hurt you, and you never know — you might find something you like!

5. Take Online Surveys

Airlines and hotels often offer points and bonuses for signing up for a deal, taking a survey, filling out a form on Facebook, etc. The points here are small (100-1,000 at a time) but, over the course a year, they can add up. United recently gave 1,000 miles to people who signed up for their dining program. American Airlines gave you 350 miles just for entering a contest to win more miles! You can sign up to various online survey sites that earn you miles and/or points just for taking surveys or answering some simple questions.

You can also earn money taking surveys (which is just as good as miles!). Again, this doesn’t have to take a lot of time and can be done while you Netflix and chill. The most lucrative companies to sign up for are:

  • Swagbucks
  • Inbox Dollars
  • PineCone Research
  • E-Rewards

6. Use Dining Rewards Programs

Similar to their shopping portals, airlines also have dining rewards programs. You sign up with your frequent flier number, register your credit card, and get extra points when you dine at participating restaurants in the airline’s network (which rotate throughout the year).

Join one of the programs in the Rewards Network (they run all the dining programs) so you can get five miles per dollar spent once you became a “VIP member,” which happens after 12 dines. So if you get those 12 under your belt (so to speak) early in the year, for the rest of the year you’ll be getting five points per dollar spent!

Many programs also offer sign-up bonuses and extra points for leaving restaurant reviews.

For example, on a $100 USD bill, you’d earn 500 points towards your favorite airline in addition to the points you’d get for your credit card spend.

It’s really simple to use, takes no work to set up, and gives you points for doing something you’re going to do anyway. With over 10,000 restaurants to choose from, there’s plenty of places to choose from!

Note: While you can sign up for every program, you cannot register a credit card with more than one. That means that if your Chase Sapphire Preferred card is tied to your American Airlines account, you can’t earn miles on your United Airlines account with that same card.

7.  Double Dipping With Crossover Rewards

There’s a growing number of companies partnering with each other and this is an amazing way to double-dip points:

  • JetBlue members can earn 750 TrueBlue points after taking your first Lyft ride (or take $15 USD off their bill). Existing Lyft members can still earn 30 TrueBlue points (up to 1,200 annually) for qualifying airport rides by linking your accounts.
  • Delta Skymiles members earn a mile for every dollar spent on US Lyft rides, 2 points per dollar spent on airport rides, and new members can get $20 USD off their first ride.
  • Delta SkyMiles members can also get 1 Delta mile for every dollar you spend at Airbnb.
  • Capital One Venture and VentureOne cardholders can earn unlimited 10x miles on eligible bookings using the “Pay Now” feature on through January 2020.

Even though the points are small on these crossover rewards, they still add up—and give you a chance to never leave a mile on the table! Check to see what other options there are!


By following the above tricks, you can maximize your points per dollar spent and cut down the time it takes you to earn free travel. This is about maximizing the points you get for the money you are going to spend anyways!

Airlines love when people actually fly to earn their miles, and they treat those who do with extra special care. However, they make it so easy to earn the frequent flier miles that it’s silly to not take advantage of the situation while it lasts. Business-class is no longer out of reach for even the most infrequent flier.

Even if you only fly once or twice a year, why not put in a couple of extra hours a month to ensure that when you do fly, you fly in style, like Pat?

Use these tips to get free business class flights and upgrade your travels! It’s what all the travel experts do after all!


Book Your Trip: Logistical Tips and Tricks

Book Your Flight
Find a cheap flight by using Skyscanner or Momondo. They are my two favorite search engines because they search websites and airlines around the globe so you always know no stone is left unturned.

Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use as they consistently return the cheapest rates for guesthouses and cheap hotels.

Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. I’ve been using World Nomads for ten years. My favorite companies that offer the best service and value are:

  • World Nomads (for everyone below 70)
  • Insure My Trip (for those over 70)
  • Medjet (for additional repatriation coverage)

Ready to Book Your Trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use when I travel. They are the best in class and you can’t go wrong using them on your trip.

Points & Miles
27.11.2013 / credit cards / SHCA / travel hacking
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