My First Year Travel Hacking: Earning Free Travel!

Our First Year Travel Hacking

Travel hacking is pretty much my greatest discovery in the budget travel world.

Warning: This is a long post, but if you want free or dirt cheap travel it’s worth it, so don’t give up!

If you haven’t heard of it, it’s a process of cycling through rewards credit cards to take advantage of the amazing sign up bonuses. It’s tricky: you have to have good enough credit to get approved, be able to charge the required amounts to the cards, pay them off each month, and not lose track of the various deadlines. If you want more information on how it all works, scroll down to the bottom of this post for some helpful links.


If you’re anything like me, you’ve seen people post about travel hacking and had your doubts.


“No way is it that easy, they’ve probably been doing it for years”


“That’s going to affect my credit score too much. I can’t risk it”


“Is it really going to be worth it?”


And then I finally dove in, and trust me, it really is that easy! Just to prove it, I thought I’d share how my first year travel hacking went: The cards, the rewards, the travel and the affect on my credit score. First here’s how we deal with our cards:

  • Start with one card at a time. Once you get an idea for your household’s spending you can expand, but start simple! You don’t want to miss the spending requirements because you’re juggling too many cards.
  • We put every single expense that we can on the card and we don’t justify excess spending because of the points. You’d be surprised how quickly every day expenses add up!
  • If you have any big expenses coming up, it’s the perfect time to get a card (or two). At one point we were renovating our house and had a Disney trip. We easily hit the requirements for two cards in only a couple months.
  • Pay the balance off every month. No excuses! This way we avoid any interest, and stay out of that deep dark pit that is credit card debt.
  • Instead of canceling your card at the end, call and ask if you can transfer the account to a no fee, no points card. Closing accounts often is not good on your credit, but if you must cancel…
  • Don’t cancel the card until right before your 1 year anniversary. That way you won’t get charged that annual fee and the impact on your credit is lessened.
  • A side note to the last point: Don’t cancel or transfer the account until AFTER you’ve transferred your points to an airline. Otherwise you can kiss all the points you’ve earned goodbye.
  • Most cards have reset times, usually 2+ years before you can get the rewards again, but if you have a business you can also get the business version, or you can use that reset time to try new cards. The one exception is American Express. Right now you can only get their rewards once per lifetime for each card. Yuck!

Now, for the cards.

Southwest Rapid Rewards Premiere Card

Our First Year Travel Hacking

I love flying Southwest. They’re a good budget airline but they don’t nickel and dime you on everything, 2 free checked bags, free snacks and drinks, and some amazing staff. They’re also pretty flexible with their cancellation policy, I’ve had great success in changing flights without any penalties. That, and the great sign up offer, is why I picked their Chase card to be my first attempt at travel hacking.

The rewards

When we got the card, you could earn 50,000 miles after you spent $2,000 on purchases in the first 3 months.

The fees

There is an annual fee of $99 on this card. I hate hate hate annual fees, however if you decide to stick with this card they do offer you 6,000 points on your card anniversary each year as a way for making up for it.

Our travel

After the bonuses and minimum spending, we had 52,000 miles plus a few thousand from previous southwest flights and extra purchases on the card. With that, we were able to get:

1 round trip from Seattle to Milwaukee (22,354 miles)

1 last minute one way from Milwaukee to Seattle (23,673 miles) Eeesh I know, definitely not an ideal use of miles.

1 one way ticket from Milwaukee to Orlando (8,498)

For a grand total of 54,725 miles.


If you take advantage of their sales and avoid last minute bookings you can do much better than we did! But I think what amounts to 2 round trip flights is not bad for our first try. If you want to sign up, you can do so here.


Chase Sapphire Preferred

Our First Year Travel Hacking

Yes, another Chase card. I had read wonderful things about this card from various travel hacking sites, specifically one detailing how we can use the points to go to Hawaii! The nice thing about this card is that the points aren’t specific to one airline. Instead, you can transfer them to various airlines and rewards programs to use them in the way that works best for you.

The rewards

You can earn 50,000 miles with this card after spending $4,000 on purchases in the first 3 months. You also get 5,000 points when you add an authorized user who makes a purchase in that time frame. This number was really daunting to me, which is why I don’t recommend to start out with it.

The fees

$0 for the first year and $95 per year after that. A lot of cards offer to waive the annual fee for the first year which is great for travel hacking.

Our travel

After rewards and minimum spending, we had 59,000 miles on our card. Because I like the card so much, we kept putting expenses on it when we had no other card, so I ended the year with 64,000 miles. While we haven’t used them yet, we do have plans to transfer them over to Korea airlines to use on a trip to Hawaii in the Spring!

2 round trip flights from Milwaukee to Hawaii (25,000 miles each)

For a total of 50,000 miles, with 14,000 leftover that we can use in the future!


I didn’t think we could hit that spending requirement at first, but we were able to time it just right and reached it with time to spare! On their site they list the points as having the redemption value of $625 but I’m not sure where you can get two round trip tickets to Hawaii for that little. This card was worth it and once I can get it again you bet I will! If you want to sign up, you can do so here.


Update: We finally used those miles! You can read more about it here.

Delta Skymiles American Express

Our First Year Travel Hacking

This was really a last minute decision. We had to book 2 tickets through Delta and while doing so I saw an offer that would really benefit us and I took advantage of it. It is usually better to put more thought into these offers and wait for the big bonuses though. Even more so with American Express since you can only do it once per card!

The rewards

You can earn 30,000 points after spending $1,000 in purchases during the first 3 months. You also get a $50 statement credit after you make a Delta purchase during that time. Another great starter card because the amount is so low! You (and a few of your friends flying with you) also can check your first bag free on any Delta flight and get priority boarding. That’s a savings of $50 per person per flight, and it can definitely add up.

The fees

Like Chase, this one also offers $0 for the first year (yay!) and $95 for each year after that. If you’re an avid Delta traveler, that’s the cost for 2 checked bags so definitely worth keeping.

Our travel

With the necessary spending (plus a little extra) we have a balance of 31,296 points. I plan on using these miles sometime in 2017 or 2018, so I have not booked my flight yet, but as an example for what I’m thinking of using it for:

1 one way flight from Milwaukee to Barcelona, Spain (30,000 miles)


While I definitely wish we’d have waited for a better deal, I’m still pretty happy with what we got from this. The cheapest one way flight on that same date from Milwaukee to Barcelona was $2,574!! Talk about some epic savings. If you’re interested, you can sign up here.

Our Credit Score

Our First Year Travel Hacking

So maybe you’re reading this going “Well that’s all well and good, but your credit had to have nose dived through all of those credit checks, new accounts, etc.” but you’d be wrong! From the start of 2016 to the end, want to guess how much my credit fell?*

6 points.

It is not entirely due to our first year travel hacking, some factors made it go up and some factors made it go down. However, you can see that if you do it right, it doesn’t have to tank your credit score!

If you are worried about that though, start small. One card at a time, see how your score changes, and move from there. Move at your own pace, because your peace of mind is worth more than any savings.

*as reported by Equifax at Credit

Final Thoughts

Sometimes juggling these cards was a little stressful: making sure we met those spending requirements, waiting to see if we got approved, making sure we paid the balance off every month. Sure the travel was “free” but there is still a cost in your time and stress, don’t forget that!

In the end though, it was definitely worth it. For the cost of one $99 annual fee and a little bit of planning and stress, I estimate we were able to save not hundreds but thousands on travel in our first year travel hacking. Without travel hacking I would not be planning a trip to Hawaii in the spring!

I can’t wait to see where travel hacking takes us in the years to come. I have a feeling it’ll help us cross off a LOT of our travel bucket list!


A disclaimer: This post is not a guarantee that you can duplicate my experiences. Deals change, households have different levels of spending, credit scores are different, etc. but I wanted to show you that it is possible for a beginner to get some amazing results!

Some helpful links:

What Is Travel Hacking? – A deeper break down of just how Travel Hacking works

The Points Guy – He frequently posts about the changes to credit card programs and some creative ways to use them

How to take a trip to Hawaii for $22.40 – We tried it and it worked! We flew to Hawaii and only spent $22.40 for 2 round trip tickets.

If you’ve enjoyed this please subscribe to follow along on the adventures we’re able to take with those miles, a summary of my second year of travel hacking, and more fun travel tips!

If you’d like to see some of where our adventures (and frequent flier miles) have taken us, take a look at our other traveling blog posts!
The Olympic Peninsula
San Juan Islands


[fts_pinterest type=boards_list pinterest_name=WanderingAcres boards_count=4]
My First Year Travel Hacking: Earning Free Travel!

Leave a Reply

Your email address will not be published. Required fields are marked *