How I Travel For Free

Traveling isn’t always cheap
, the flight alone can cost nearly just as much, if not more than your entire trip. To many destinations, it’s the most expensive part of your trip! So imagine if you never had to pay for a flight again, how great would that be? Well, that’s my plan and so far it’s working quite well as I haven’t paid for a flight since 2014. I’ve flown to Israel, Kauai, Oahu, New York, Miami, Vegas, and currently have another trip booked all for free – thanks to my points and air miles. Points and air miles can be acquired in many ways, but here are some easy tips to begin earning and start flying for free:


If you have your own business, by all means go and get the Chase Ink Business Preferred for that 80,000 point reward bonus. If you don’t have your own business and you’re ready to get a(nother) personal credit card, I recommend signing up for either Chase Sapphire Preferred or Chase Sapphire Reserve. Both cards feature zero foreign transaction fees, when some cards can vary up to 3% in fees. They are both VISA cards, which is widely accepted globally, because even in 2017, traveling with an AMEX in some small or rural countries is really annoying. They also both reward you for your travels, Preferred gives you 2X points and Reserve gives you 3X points for every travel and dining purchase, 1/$1 on all other purchases. Finally, in my opinion, the biggest incentive to sign up is the 50,000 point reward bonus. This bonus is obtained if you spend $4,000 within the first 3 months of opening your card.

For some, it may be difficult to spend $4k in 3 months, but if you pay for everything (bills, food, gas, etc) that you can with your card, it shouldn’t be an issue. If it still is an issue, then worst case scenario, you can Venmo or PayPal someone you trust the remaining amount needed to receive your bonus (this will charge you a 3% fee from Venmo or PayPal, but let’s say you only need to spend $1000 more to qualify, that’s just $30 in fees to ensure you receive your 50k bonus) and then you collect your cash back from your trusted someone to pay towards your card balance.

Preferred has an annual fee of $0 for the first year, then $95 each following year.
Reserve has an annual fee of $450 (charged immediately), but with a $300 travel reimbursement*

*If you are spending up to $300 a year on anything travel related (that includes flights, hotels, taxis, UBER, parking garages, parking meters, etc.) then you will be reimbursed at the end of the year for those purchases. Therefore, suddenly your whomping $450 annual fee is $150, just $55 more than the preferred.

Preferred rewards you with 25% more in travel redemption. That means 50k points is worth $625 towards travel. Reserve rewards you with 50% more in travel redemption. That means that 50k points is worth $750 towards travel. In other words, that 50k bonus just for signing up is worth $625 or $750!

See! Even Chrissy Teigen knows what’s up.


This one is a bit more tricky and can be time consuming, but it’s very effective if done well.

If you have a Chase credit card, then you’re already accumulating points through the Chase Ultimate Rewards program with every purchase made. In addition to those everyday points received, you can earn even more points by shopping within the Ultimate Rewards portal with participating retailers. With hundreds of stores offering up to 20X points, why not earn extra miles at the stores you probably already shop at? This is a very fast way to multiply those points and save up for your next flight (i.e. 4X points at NIKE)!

If credit cards aren’t your thing, then you can still earn points similarly with American Airlines. First off, when flying with AA, I’m always sure to add my AAdvantage Number to each flight, this also includes any partnering airline (Oneworld Alliance). Even if you didn’t pay for your flight, (i.e. if your boss paid for a business trip) then whoever is flying is the one that is able to collect the miles. So don’t forget to claim your miles from every trip!

The downside to booking flights through the AAdvantage portal is that unlike booking through Chase Ultimate Rewards, you must pay for your entire flight with either miles or cash (and no, the 1:1 points program with Chase does not include AA). Therefore, if you have 11k miles and you need 15k miles, you either need to purchase miles (approx. $30/1k miles) or earn the remaining 4k. Now, I think that buying miles is a scam; you may purchase only multiples of 1k miles, even if you only need 1 more mile to travel. A 15k flight may only cost $200-$300, yet buying 15k miles costs $442.50? You also get nothing out of buying miles besides the purchased miles. Buying miles instead of earning them is like buying something with cash verses a credit card, if I’m going to spend money, I want to be rewarded for it. Therefore, go check out AAdvantage eShopping and see what you can earn. Be very careful to read the qualifying rules for each purchase, additional codes not listed online may disqualify your ability to redeem miles.

For example, I earned 1,900 miles by spending $64.07, granted I could have bought 2,000 miles for $59, but in addition to my accumulated miles, I got 4 bottles of wine and 6 meals delivered to my door. Plus, all of that food and wine is valued much over $64 and I get miles with it? Fantastic. With that said, here’s how it’s done:

1. I signed up for a Winc membership through AAdvantage eShopping. There is a 900 point bonus just for signing up and you can receive $20 off of your first order, you don’t have to stay a member to receive the points, you can cancel after your first delivery. So I spent $34.13 and received four preselected bottles of wine delivered to my door and they were delicious.

2. I signed up for a HelloFresh membership. There is a 1000 point bonus just for signing up and you can receive $30 off your first order, again, you don’t have to stay a member to receive the points, you can cancel after your first delivery. So I spent $29.94 and received six preselected meals, portioned, and ready to cook delivered to my door and yes, they were also delicious.

There are constantly deals going on all the time. Any time I want to make a purchase online, I will always check if AAdvantage eShopping has a deal going on. The beauty of this is that I’m not only receiving miles through my purchase, but I’m also being rewarded with points for every dollar spent through my chase credit card, WIN.


I understand this isn’t technically traveling for free, because yes, you have to spend money to earn points and/or miles… but, if you’re already spending money every day as I’m sure every person reading this post is, you might as well be rewarded for it.

There’s also plenty of other credit card options and airlines with similar benefits – these are just examples of the two ways to earn that have worked best for me! Finally, I was not sponsored for this post, in case you couldn’t tell, I’m not exactly famous, so these are just my good ol’ suggestions!

Finally, I have to throw some credit to the original master of travel, The Points Guy, he’s the reason why I started researching all of this stuff and we can all learn a thing or two from him. Plus, he has helped rescue three Frenchies and one of them is named Miles, so that’s reason enough for me to give him credit on my mediocre blog.

Miles + Hootie + Swisher