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How I Travel (Mostly) for Free

Be warned, this is less about writing, and more about how I was able to travel so much and find inspiration.


Friends and foes alike have commented on my travel habits.

Usually with just a bit of longing in their voice. Which is fair, as I've been given far more than my share of opportunities to see other cities and countries.


Just in 2019, I've been to Las Vegas for CES, Barcelona for La Merce, Munich for Oktoberfest, New York for the pizza, Boston for the fall, Albuquerque for the Balloon Fiesta and Meow Wolf, numerous trips to Dallas, a jaunt to Austin for the release of The Man Who Killed Don Quixote, Houston for a beach frisbee tournament, was booked for Chicago but ended up coming home due to the knee injury, and Portland to see a friend and Powell's Books.


Damn boi, brag much?


So ya, it was a pretty great year, but guess what? I don't have the money for all that travel....

Now admittedly, I have my father to thank for a lot of this, if not all of it. I'm cheating on two ends with the travel hacking, but even if you lack nepotistic resources, you can still achieve a fair bit of success and travel for A LOT cheaper than the average person.


Here's how, and a warning- the link to Chase is a referral link, and I'll be getting bonus referral points if you get a card through it. (I mean, it’s the same process for you, I just happen to get points, so thanks).


1) Get a feed going with Scott's Cheap Flights.

  • Pick where you want to go. Keep an eye on it. Be ready to spend money and be flexible.


2) Get a Southwest Rapid's Reward card. (Oh no, the dreaded referral link where you might help someone who told you about the company. -egads-). Also, if you'd prefer a different card all together, you can do something similar with any Chase card, I'm just a fan of the companion pass more than anything. Here's another link to a chase card that has pretty good offers: Chase Ink

Here is where it gets tricky, though.

  • The goal: a companion pass, and a crap ton of points.

  • A companion pass- BOGO plane tickets through Southwest Airlines.

  • Points- Southwest Airlines currency you can use to buy flights. 20k-30k points is roughly a roundtrip flight to most anywhere.

  • Step 1: Earn the sign up bonus. This is by spending “X” amount of dollars in “Y” amount of time.

  • If you can’t churn the cash flow (hey, thanks again dad), you can use the Venmo option where you send someone you trust the money and take a 2% hit instead of actually spending $5k.

  • Step 2: Put ALL your expenses on the card. Anything you’d actually be spending money on like groceries, gas, entertainment, etc, you drop on that card.

  • If you can, get all of your business/work/company expenses on this card as well for re-compensation. That’s even more fun as you don’t pay for anything.

  • Step 3: Either have someone that’s working for this with you (like an S/O, or really good friend) sign up for the card to get a referral, or sign up for a second card yourself to get the additional bonus sign up points.

  • Step 4: Companion pass and 100k points acquired, now to save on travel.

  • Get that friend or S/O to split the plane fare with you. Or if you really like them, you split the hotel. Still a cheap A.F. trip.

3) International Travel, putting Step One and Two Together

  • Using points, unless you already live in NYC or LA, you’re able to get to one of these destinations for free, essentially.

  • This is key, as Scott’s Cheap Flights doesn’t really have flights that match Southwest’s point system. But it does help you find insanely discounted flights from these cities to ones abroad. (NYC to Barcelona, $250 or so semi regularly).

  • Flexibility- These cheap flights are usually weird lengths of time. You may have to spend 6-10 days abroad, which can be hard to swing. Save up that PTO, nail a holiday weekend, and you should be able to pull it off.


Thanks to a sauna chat with Jordan, and a coincidental email from Chase for making this quick and dirty blog post happen.

Much love,

Andrew Monroe

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