How I Travel for Free

I heard about “travel hacking” a few years ago, and it didn’t seem like it was something for me. It sounded like extreme couponing but for flights instead of toilet paper and processed food. It also sounded like it was breaking a lot of rules, and I’m a rule follower, not a rule breaker. Since learning the ropes and developing my system, I’ve flown to India, Latvia, San Miguel, Quebec City, Peru, the U.K., and multiple domestic destinations. I rarely pay for flights or hotel rooms.

What I love the most about travel hacking and having points at the ready are the options it affords me. I was able to treat my husband to a first-class flight to Denver for his birthday; fly my daughter in to go to Bonnaroo with me, and I flew my son home for Christmas. All for free.

In this post, I’m going to tell you how I learned all the information about travel hacking, what I do daily that keeps me in reward points, and how I’m keeping up with the ever-evolving rewards programs.

Before I get started, I want to point out that this is not a passive process. You will have to do work and research and stay organized and up to date. Free isn’t free. Once you make it part of your life, though, it will get easier. It’s just developing a habit.

First, I educated myself. I took the course on Creative Live by Chris Guillebeau and Stephanie Zito. At the time, it cost me over $100 and took me a better part of a week to get through. It’s now cheaper ($34) and, even though some of the information may be out of date, I still consider it the gold standard of travel hacking. You will learn about EVERYTHING! I felt overwhelmed, but I was able to find the things that I was comfortable with incorporating into my life.

Another course I just completed is Jetset Lisette’s. She exclusively talks about applying for multiple credit cards for the bonus miles then canceling them. She consistently keeps a million points a year. This method is covered in the Creative Live course, but since it was in with a bunch of other information, I felt overwhelmed by it and thought it was more than I could handle at the time with my limited organizational skills. The way Lisette presents it is so reassuring she gave me the confidence to add that to my arsenal. The thing with this hack is you have to be very organized, and your credit score needs to be in the 700s at least. This hack also requires the heavy use of spreadsheets, which Lisette provides when you take her course.

Second, I had to make sure I had the right credit cards that also had the biggest sign-up bonuses. That makes all the difference. I already had the Chase Sapphire Preferred, and I changed my business card to Chase Ink for Business. I highly recommend both of these cards, especially the Ink for Business. You don’t have a business? Honestly, make it up. I told you I wasn’t a rule breaker, but they didn’t ask for my tax ID number, and the worst they can say is no. It’s how I get most of my points, so it’s pretty important. If you use a certain airline more than another, it could pay to get their airline card. I mostly fly American and its partners, but a lot of my west coast friends use United and Alaska. It depends on where you live and where you want to go. It also depends on their sign-up bonus. Since I am now closer to Atlanta, I recently signed up for the Delta Skymiles Platinum Card for their 100,000-point bonus. I also added the IHG card and Hilton Surpass.

One thing to note, when signing up for a new card with a sign-up bonus, they have a minimum spend, like $5000 in the first three months you have the card. You will need to spend that to get the bonus, so make sure you can meet it. Don't sign up for three cards that have $5000 minimum spends if you can't spend $15,000 in that first three months. Business cards have a much higher minimum spend so sign up for those when a big project is coming up.

The third thing is figuring out what cards offer a bonus on certain purchases. The Chase Sapphire Preferred is better for dining out. The Chase Ink for Business gets bonus points for utilities (so all cell phones and utility bills go on that card), travel (gas, hotels, and any travel expenses I have to book), and office supplies. That is the biggest point earner getting 5 points per dollar spent at an office supply store (it, unfortunately, is now only three but still not bad). I just saw a Hilton card that gets 6 points per dollar on certain purchases.

Simply, my method is essentially taking the money I’m already spending and spending it in a way that maximizes the bonuses I get on my cards.

Say I need something from Home Depot. I figure out how much it's going to be and head to an office supply store (Staples or Office Depot) and get the appropriate amount on a gift card. You can't do this with everything but, if you can order the item online and pick it up in-store, you can get extra miles. If that is an option, I then go home, go through a shopping portal (I use Chase and American Airlines) that has the most points per dollar, and order the item to then be picked up at the store or shipped paying with the gift card. During my kitchen renovation, I did a lot of Home Depot/Lowe’s shopping this way and racked up lots of points. I get 5 points per dollar on the gift card then an addition 2-5 points going through a shopping portal. That doesn't sound like a lot, but it adds up pretty quickly.

There are gift cards for almost anything. I buy all my gas with a gift card even though I get three points per dollar just by using my Ink card, the gift card is five points per dollar. You can get groceries, Amazon cards, even Delta, Airbnb, and Amtrak. I have found that Staples has the best variety of gift cards, but Office Depot has more cards that you can get with a range instead of a set amount. That helps when you are buying something big like an appliance. You can get two cards with $500 each instead of wiping out their entire supply of $100 cards.

When I am ready to book a trip I normally go through Chase to book the reward flights. Some people take the Chase (or bank points) and transfer them to the airline and then make a booking through the airline. I don't do that because booking through the Chase site counts as a retail purchase from the airline and I will get those miles counted to my frequent flyer account for that airline. I then wait until my airline account has enough points to get a ticket to then book through them.

What to do if you don't have enough points in one account to book your whole trip? You can transfer the points to the airline or you can book your outbound ticket from one account the the return ticket from another one.

I've been able to easily book my travel using this method but I also travel a lot by myself or with my husband. I don't have a family I have to move around. If that is the case for you, you will probably need to earn points in bigger chunks like Lisette talks about in her course. One of the important takeaways I got from Lisette was when a big expense is coming up (kitchen renovation) that's the perfect time to apply for a new card to meet the sign-up bonus. I was leaving points on the table by not doing that.

The travel reward landscape is always changing (see the Ink Business drop from 5 points to 3). The best way to keep up is to subscribe and follow TPG - The Points Guy, and Million Mile Secrets.

This process might sound like a lot of trouble, and it is. It takes me a lot longer to buy something which does have its benefits. I no longer impulse buy. I'm spending less money but getting more out of what I'm spending. This method has less to do with consuming and more to do with consuming well.

Please let me know if you have any questions and if this is something you want to do a deeper dive in, I recommend the Creative Live course or Lisette's. If my disorganized brain can do this, so can you.

Happy (Free) Travels!!