How I Travel for Free, in Style, Every Time

A few years ago, I decided I'd had enough. I'd had enough of paying exorbitant prices for international flights. I'd had enough of airports and all the anxiety and discomfort they induce. I'd had enough of travel being a struggle.

I decided to make it a luxury instead. 

I set three outrageous goals:

1. Never pay for flights again.

2. Never wait in line at airports again.

3. Always have access to at least one lounge, no matter what airport I'm in.

In other words, travel like a boss.

Well, I'm happy to say, after years of research and practice in the art of "travel hacking," I have finally achieved all three of my goals, and thus, Boss Status.

What follows is MY strategy to accomplish the three goals above. 

NOTE: There are countless blogs, books, and resources about travel hacking and points acquisition. This is not intended to be a comprehensive overview of the travel hacking "game" and everything it entails. Rather, this is me revealing how I have personally decided to play (and beat) that game. 

There is no ONE method for beating the game. There is no one credit card that EVERYONE should get. There is no magic formula. This is because we all have different spending habits. We all have different airline preferences. If there's one thing I learned from mastering how to "hack" the travel game, it's this: Do What Makes Sense FOR YOU.

So, here's what makes sense for me.

I use four primary credit cards to accrue points (which, compared to some travel freaks, is nothing). They each serve a distinct purpose for me.

Three of my cards are Chase cards. I have the Chase Sapphire Preferred, the Chase Ink Business Plus, and the Chase Freedom Unlimited.

Last but certainly not least, I have the American Express Platinum card.

NOTE: Before I write another sentence, let me say this: don't even think about playing the credit card points game if your credit score is poor. If your credit score is poor, stop reading travel hacking blogs and start reading credit/finance blogs. You can't run a marathon without training first. Repairing damaged credit is the training. Then you can race.

For EVERYTHING I buy, I ask: How can I get points for this? AND: What's the most possible points I can get for this? And the answer dictates which credit card I use to make the purchase, and where exactly the transaction takes place. 

Here's exactly how I use each of my four primary credit cards:

Chase Sapphire Preferred - This is my go-to card for restaurants (2x) and travel expenses (2x). The sign up bonus is 50K points. I used it for flights and hotels in the past, but now I use my Amex Platinum for those purchases (I'll explain why below). However, I still use this card for miscellaneous travel expenses like rental cars, train tickets, and Airbnbs. 

Chase Ink Business Plus - I got this card with a 60K bonus. I love it (even more than the newer Ink Business Preferred card) because it pays 5x points at office supply stores. My favorite all-time travel hack is buying Amazon gift cards at Office Depot (in person), and essentially getting 5x points on everything I buy on Amazon (appliances, camera equipment, etc.), including groceries which I buy on Amazon Fresh. I drive to Office Depot every couple weeks and buy a $500 Amazon gift card. That's 5,000 points per month--over 50k miles per year--with practically no extra inconvenience (the small inconvenience of going to Office Depot is negated by having my groceries delivered to my doorstep). 

The Ink Business Plus card also pays 5x on phone and cable bills. I've automated payments of my AT&T bill to this card. That's another 500 points per month, or 6,000 points per year, without doing any extra work. 

I also use this card for gas (2x). That's another 200-300 points per month. 

So from this card alone I'm getting enough points for a round trip international ticket (~30k miles each way on the low end).

Chase Freedom Unlimited - I got this card to improve my "credit mix", which is a small factor in your overall credit score. (Having more cards actually improves your credit, assuming you use them responsibly). I thought about upgrading my Chase Sapphire Preferred card to the snazzy new Chase Sapphire Reserve, but because I already have the Amex Platinum card (the Chase Sapphire Reserve's #1 rival), adding another card with overlapping benefits and another hefty annual fee didn't make sense. I needed a new card, and after much deliberation, I settled on the Freedom Unlimited. 

The Freedom Unlimited is a cash-back card. It pays 1.5% cash back. But if you have another Chase credit card like the Sapphire Preferred, that cash back counts as Chase Ultimate Rewards points (1.5 points per dollar).

Even though the Freedom Unlimited has only a meager sign-up bonus ($150 back after you spend $500) and therefore might not seem like the best "travel card," I've found it to be an excellent supplementary card. Getting 1.5x points on ALL purchases is nice! I use this card for every purchase that I cannot get a higher bonus from with one of my other cards (OR from shopping with on the Chase Ultimate Rewards portal, which I will say more about below). It's my default card. I use it for buying clothes. I use it at Target. I've even used it to pay taxes. I use it when there is no better option. And I feel great about it, because at least I'm not settling for 1 measly point per dollar. 1.5? I can live with that.

Amex Platinum - This is the Boss card. I got an offer in the mail for a 100K sign-up bonus and couldn't resist. I believe the current bonus stands at 60K.

The perks with this card are ridiculous. Mainly, I love it because it covers my third goal: lounge access. I now start every trip out of my home airport, Sea-Tac, with yogurt and fresh berries (and the occasional mimosa) in the Amex Centurion lounge. If you fly Delta, the Platinum card will also grant you access to Delta lounges. (There's a brand new Delta lounge at Sea-Tac; I'm excited to fly Delta so I can try it out.)

But best of all it includes a Priority Pass membership. I remember waiting to board a long-haul flight from Papeete, French Polynesia, to LAX. The computer system crashed at the airport and the boarding situation was pure madness. There was also no air conditioning in the terminal. Luckily there was a comfy Priority Pass lounge up one flight of stairs from my gate. I washed my face, brushed my teeth, changed clothes, and had a few cocktails before finally boarding my flight. Amex Platinum FTW. 

Air New Zealand lounge (Priority Pass), Sydney Airport

The new Chase Sapphire Reserve card put a lot of pressure on Amex to boost the benefits of the Platinum card. Amex responded by offering 5x points on airline and hotel bookings. Amazing! (Although they also raised the annual fee from $450 to $550--not so amazing.) I used to use my Chase Sapphire Preferred card to get 2x points on flights and hotels. Now I use my Amex Platinum instead with no hesitation. The $15/month Uber credit they just added is also a nice touch. Not to mention the preferred status with Starwood, Hilton, Avis... This card is just sweet. 

If the $550 annual fee sounds brutal, this hack takes some of the sting away:

The Platinum card offers $200/year in "airline credit" for the airline of your choice. This credit is intended to cover things like baggage fees and seat upgrades. But it also works on airline gift certificates (in denominations of $50 or less, according to word on the street). So in four separate transactions, I bought four $50 Delta gift cards and was credited back all $200. Essentially $200 worth of Delta, for free. Yes, please. 

The Amex Platinum card also helps me accomplish Goal #2: Never Wait in Line at Airports. Another perk of the card is a Global Entry fee credit. (Global Entry includes TSA pre-check, but TSA pre-check does not include Global Entry, so make sure to get Global Entry first to avoid paying both fees). I actually had Global Entry before I got this card, BUT I used the credit to get free Global Entry for my wife. In other words, you will still get reimbursed if you buy Global Entry for someone else. 

Global Entry and TSA Pre-Check are must-haves! Why wait in line with the peons when you can waltz through security?

The only problem with TSA Pre-Check is that it's not always a waltz. It's faster than the normal security line, but there is still a line.

I recently enrolled for CLEAR, which allows you to cut even the TSA line. You scan your fingerprints and walk straight to the conveyor belt. It can be used in conjunction with TSA Pre-Check, so you can keep your shoes on too. 

CLEAR is $179 per year, which only makes sense if you travel regularly. However, it's only $50 to add a family member. So if you travel semi-regularly with your partner, it might be worth it.

Disclaimer: I haven't actually used CLEAR yet. I signed up and attempted to undergo the initial screening (done at a kiosk at the airport), but the machines couldn't read my wife's driver's license, and there was no way to enter the info manually, so we couldn't actually use it. Very disappointing. My advice is bring your passport to the airport for that initial screening on the first day you plan to use the service. Bottom line: it's another way to make airports easier to navigate. It saves time--time that could be spent eating blueberry scones in the Centurion lounge. 

Imagine this:

You're going on a trip. You take an Uber to the airport. You use your $15 monthly Uber credit and the ride that usually costs $40 costs just $25. You walk straight to the security checkpoint, skip the line with CLEAR and TSA Pre-Check, and are through security less than five minutes after pulling up to the curb. You relax in a lounge and eat a bowl of oatmeal with coconut flakes. You sip a dopio espresso macchiato and read the Wall Street Journal with your feet up. Then you head over to your gate to board the flight you paid $0 for, because you used points to cover it entirely. The only thing that's missing is First Class. (Just go for it.)

What happens when I run out of points?

Get more. 

You can always sign up for a new credit card, but the best thing to do is shop smarter.

I ALWAYS check the Chase Ultimate Rewards portal for bonus offers before I buy anything online. Not shopping through portals is just stupid. For stores that I visit frequently for home goods and ordinary STUFF, like Home Depot or Target, I always try to shop through Chase to take advantage of bonus offers. If you prefer to buy stuff in-person at an actual store, consider placing the order online to get the bonus, then picking it up at a retail location. You'll get extra points AND save yourself the headache of shopping. 

Shopping through the portal is especially worthwhile when you're making a big purchase, for example, a new phone or laptop. I recently bought a new iPhone at the Apple store. Instead of checking out the normal way, I logged into the Chase portal (at the store--I'm shameless) and made the purchase online to get 3x points. Then I turned to a sales rep and said, "Hi, I'm picking up an order I placed online." And he grabbed it for me and I left. 

Valentine's Day? I was going to buy her flowers anyway...why not buy them via the portal? ProFlowers was offering a whopping 12x bonus. 1,000 extra miles--sure, why not?

Printer low on ink? Buying a fancy coat? New shoes? Shop through the portals! Try stuff on in an actual store if you must--then go home and order the same thing online, with benefits. 

Some other ways to accrue miles: 

Pick up the tab for big group expenses and have everybody pay you back.

Company flying you to Milwaukee? Pay for it yourself and have them reimburse you. 

I even heard there are services to pay your rent with a credit card. Might be worth looking into.

You can get as extreme about it as you want. Personally, I enjoy the challenge of "beating the system" and find few things to be more satisfying than booking an expensive flight purely with points. 

Don't just buy stuff. Buy stuff--and choose your credit cards--strategically. Points add up! 

Ask me anything in the comments below!