Credit Card Hacking, How to Travel Affordably

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How do we afford to travel?

I’m often asked by friends how James and I manage to travel so often and more importantly, how we afford it all? Credit Card Hacking is part of the answer. We’re both quite fortunate that we have extensive PTO programs with our respective jobs, so we’re able to take time off easily. Additionally, I travel every week for work. This has afforded me the ability to earn hotel points, airline mines, and rental car points quickly and naturally without costing me anything.

This perk bundled with cheap travel has given us the opportunity to see more than 20 countries together, practically free! However, not everyone travels for business and is able to earn large amounts of points/miles naturally.

You could in theory earn points/miles yourself “naturally” through your regular traveling. However, it would probably take too long to accumulate enough points/miles for a flight redemption or hotel stay via that route.

DON’T WORRY! There is a work-around to this. Let me introduce you to the world of Credit Card Hacking!

What is Credit Card Hacking?

When I say Credit Card Hacking – I’m not referring to literal hacking. There is absolutely nothing illegal about this process. It’s simply working the system to your advantage. Essentially, credit card companies such as Chase, Capital One and American Express offer conditional “sign-up” bonuses for first time card users.

Chase offers 60,000 UR Bonus Points, if upon opening a specific Credit Card, you spend $4,000 within the first three months (the condition). 

Why do we care about 60,000 Points? Currently 60,000 UR Points are getting my parents two round trip tickets from NY to Italy for my wedding. They won’t have to pay a cent for their flights to Italy. Interested now?

So how exactly do you do the ‘hacking’? Simple – earn as many points as possible. The easiest and fastest way to do this is by attaining Sign Up Bonuses. However, it is crucial to do this in a fiscally responsible and strategic manner. Also, day to day spending using the right credit card is key. For example, most cards offer 1 point for every dollar spent, but some may offer 2 or 3 points for every dollar spent on travel, or food etc.

If earning free flights and hotel stays without costing you anything sounds like its for you, then buckle up and keep reading.

Everything You Need to Know about Credit Card Hacking

Cash is NOT King (that includes Debit Cards).

Firstly, you need to understand why credit cards are more value-able than debit cards, or cash. When you use a credit-card you have the ability to earn points/miles/cash-back on your spend.

Let’s say you spend $10 cash (or via debit-card) on a burger. All that occurs in this transaction is you’ve spent money, and received a burger in exchange. However, if you paid with a credit-card, not only would you be exchanging money for a burger, but you would also be earning cash-back or points/miles.

Additionally, using credit-cards can offer you various protections such as rental insurance, purchase protection, and travel benefits that cash/debit cards do not provide. For instance, if you booked a flight with a travel credit card and the airline lost your luggage, you are normally out of luck. However, a travel credit card may cover the cost of replacing clothes and toiletries you now need to purchase while on your trip. A regular debit card, or cash purchase doesn’t offer that benefit.

Credit Card Knowledge

It’s also important to employ fiscally responsible behavior when it comes to Credit Cards. While these sign-up bonuses are attractive, and you may want to jump right into this credit-card world, it’s also important to educate yourself on how to responsibly use a credit card.

Just because you have a credit card, doesn’t mean you can swipe without consequences. At the end of the day you’re still responsible for paying off every dollar you put on your credit card, along with any interest you may accrue. If you use your card smartly, you’ll never put yourself in a position where you accrue interest, nor in a position where you can potentially damage your credit score.

My personal viewpoint with credit cards is that it is an intermediary step between the item I’m paying for, and my bank account. I never purchase something I cannot pay for directly from my bank account. I also never purchase something I wouldn’t purchase if I had to pay in cash/debit card.

What are points/miles?

Points/miles are essentially a currency earned for being part of a loyalty program. If you’re a loyalty member of a hotel chain, or an airline you may be familiar with the concept.

If you enroll into Delta's free SkyMiles Membership Program, fly with them a few times a year - you will earn miles. These miles can then be used to redeem a flight.  

Loyalty programs are available with all hotels/airlines/rental-cars and are free to join. The amazing thing is the concept of a loyalty program is not limited to strictly hotels and airlines. Credit-Cards offer them as well – hence the blog post.

The fundamental principle in earning points/miles is that you earn them based on spending you HAVE to make. Regular, day to day spending. You absolutely NEVER want to spend money on things you had zero intention on buying solely to earn points/miles. At that point you may as well just pay for the hotel/airfare out of pocket.

Value of Credit Card Points vs Value of Hotel/Airline Points

A key difference I’d like to highlight is the difference between Credit Card Points compared to Hotel/Airline points. Hotel and airline points generally can only be used with the respective company that you earned them. However, Credit Card points can often be transferred to “partners” and gives you the ability to use your earned points over a multitude of platforms.

For example, Chase’s points are called “UR” points. UR points can be redeemed directly through Chase’s travel portal for various companies, or they can be transferred to their partners and be redeemed directly. Here’s a list of Chase’s transfer partners:

  • Aer Lingus AerClub
  • Air France/KLM Flying Blue
  • British Airways Executive Club
  • Jet Blue TrueBlue
  • Singapore Airlines KrisFlyer
  • Southwest Airlines Rapid Rewards
  • United MileagePlus
  • Virgin Atlantic Flying Club
  • Iberia Plus
  • Hyatt Gold Passport
  • IGH Rewards Club
  • Marriot Bonvoy
  • The Ritz-Calrton Rewards

Each Credit Card company has their own respective set of transfer partners. Airlines and hotels also have transfer partners, however they’re not usually as extensive as credit-card companies.

Which Credit Card Should You Get?

Based on Need

There are tons and tons of credit cards out there, and each of them are geared towards different needs. I highly recommend searching through websites such as 10xTravel, ThePointsGuy and NerdWallet to compare the various credit cards out there.

Interested in a travel credit card? There are many great cards for that, such as the Chase Sapphire Preferred, Chase Sapphire Reserve or The Platinum Card from Amex. How about a card that offers benefits for small businesses? Yup, there’s a bunch out there for that including the Ink Business, or the Capital One Spark. Want a card geared towards earning cash back? There’s even a card for that from Discover It, to the Citi Double Cash Card. Again, I HIGHLY recommend searching through the above-mentioned websites to compare various cards and find the right one for you.

5/24 Rule

It is worth mentioning that in this world, Chase points are quite valuable, and Chase is quite strict. Essentially, Chase has implemented a “5/24” rule that is stringently enforced. The rules goes that if you have opened 5 or more personal credit cards within the past 24 months you will most likely get denied on any Chase Credit Card Application. Typically “business” credit cards are excluded from your count towards your 5/24 status, however there are some that are included. Additionally, your 5/24 status also considers if you are an Authorized User on someone else’s credit card.

On almost any credit card hacking website, I guarantee you will see cards ranked by your 5/24 Status. Most websites will suggest the best card promotions you should attack if you’re below 5/24, and which card promotions you should attack if you’re above 5/24.

The general rule with 5/24 has been, if you’re below – you go for Chase Cards, since Chase is the one implementing this rule for their application process. If you’re above, you look at other vendors such as Amex, Capital One, Citi etc.

Earning Points on Credit Cards

Sign Up Bonuses

The fastest way to earn points is through “sign-up” bonuses. In order to attain a Sign Up Bonus you need to meet the requirements of the specific card’s promotion. Most cards require you spend a certain amount within your first 3 or 4 months.


Typically your clock for your 3/4 months begins on the day which you were approved for your credit card – not when you receive it. This is important because you can often sign-up online, get approved and won’t receive your card until maybe a week after.

Minimum Spend

Often, people are concerned with meeting the minimum spend (MS). Like I said earlier, you never want to spend “additional money” in order to meet a minimum spend. The MS should be met through normal expenses. In the past I’ve personally signed up for credit cards right when I knew I had big purchases to make.

Some large payments you can put on your credit card to meet your minimum spend are your rent, car payment, or even tuition. If you don’t have those types of payments consider asking someone you trust. Do your parents have any large expenses they’re planning to make and can charge to your credit card and reimburse you? How about your significant other?

An important point to note is credit card fees. Sometimes paying with a credit card for certain things incurs a fee. I know personally when I paid my school tuition and my rent both vendors charged me a fee due to credit card processing fees. For example, paying my $1500 rent bill with a credit-card also resulted in a $40 fee to me. Personally, that was a fee I was willing to accept. While I totally believe you shouldn’t spend beyond your normal spending in order to meet a MS, I believe a $40 fee is worth the potential of a free round trip flight to Europe.

If you would like to avoid fees like this, but still want to put your large expenses on your credit card, I suggest reading up on Plastiq. This company basically allows you to pay virtually any bill, with a credit card for a small fee. It may be worth considering if their fee ends up being less than your vendors fee. This also works great in instances where you can only pay your bill via check. You essentially would pay Plastiq through your credit card, and they in turn would pay your bill via check on behalf of you.

Everyday Spend

Once you have hopefully achieved your bonus, you can continue to earn points through regular daily spend. There are tons of different credit cards out there that are geared towards different categories. Just be mindful of what type of spend you are incurring, whether its travel, business, or food related, and what cards you have that best suit those needs.


Credit card companies not only want you to sign up, but they want your friends to sign up too! Many offer bonus points if your friends/family apply for a credit card through your referral link.

Chase is offering a 60,000 Sign Up Bonus and also has a 15,000 referral bonus. If I refer someone and they successfully apply for a credit card (meaning they got approved), I also get the referral bonus. In this scenario I could walk away with a total of 75,000 points.

Two Player Mode

A great strategy to use when entering this credit card hacking world is the “two player mode”. Two Player Mode basically means you and (typically) your second player combine your points.

I attain my sign up bonus and then refer James, and now have a total of 75,000 points. James attains his sign up bonus and now has 60,000 points. Together we have 135,000 points which we can pool in one account and use for the both of us.

Redeem Points Smartly

Where to Redeem Your Points

Where you ultimately redeem your points is important. There are advantages and disadvantages for redeeming with transfer partners or through a travel portal.

If you book through Chase's portal and you have a CSR your points are valued at 1.5x. Meaning if you have 10,000 points, your 10,000 points will be worth 15,000 points and your points can go further.

However, it may not always be the smartest idea to book through the Portal. Let’s say you want to book a Delta flight through the Chase Portal and it costs 75,000 points. You only need 50,000 points since they are worth 1.5 their value- okay not bad. BUT that same flight through Delta itself, may cost 40,000 miles. In this case it would make more sense to transfer your UR Points to Delta SkyMiles and then redeem the flight through Delta. It’s so important to research, research, research when booking your redemption.

When to Use Your Points – Valuation

There are tons of websites out there that tell you the “cash value” of your points. My favorites are 10xTravel, ThePointsGuy, TheNerdWallet and ThePointCalculator. These websites also offer tons of resources about the credit-card hacking world.

The general rule is you shouldn’t book a redemption award if the “cash value” of your points is significantly more than what it would cost you to pay out of pocket.

If Marriot Bonvoy points are worth 0.8 cents, then that means 100,000 points are worth $800. If the out of pocket cost for your redemption is $300, you probably should opt to pay for it yourself versus using your points.

However, just because the cash-value of your points may be higher than using actual cash, doesn’t mean you shouldn’t use your points. At the end of the day the value of your redemption is based on what you deem important. If you have the points, and money is tight, it may make sense for you to use your points. You need to make the best decision for yourself, just ensure its an educated decision.

Now Start Hacking

As this is a Travel & Lifestyle Blog, I’m assuming you read this post because you were interested in how to travel for less.

I highly recommend the following:

  • Familiarize yourself with your Credit Score and how it is calculated and impacted.
  • Read up on the Chase Sapphire Preferred – the first travel card I recommend getting (post coming soon).
  • Do your own research about this travel hacking world – and check out all the aforementioned sites.
  • SIGN UP for the promotional bonuses and start earning those points!

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