How I Travel Hacked 3 Free Round Trip Tickets to Hawaii

A special shout out to Michael The Honeymoon Guy for teaching me the ways of Travel Hacking, in which you sign up for a bunch of travel credit cards to take advantage of the signup bonuses.  He wrote a post on his blog how he helped me figure out how to score my tickets to Hawaii. 🙂 This is my version of the events. 

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In October, my whole family will be celebrating my parents 40th wedding anniversary in Hawaii. Since my parents have a timeshare (yes, I know they’re the worst) we only needed to cover the cost of our flight. As a huge credit card nerd, I figured I could sign up for a few cards and travel hack some cheap airfare.

On my very first attempt at Travel Hacking, I was able to SAVE $1941 in airfare.

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You read that right. That was not a typo.  For three round trip tickets from LA to Hawaii, we paid ABSOLUTELY NOTHING.

How I Hacked Hawaii
The cards I signed up for:
Chase Sapphire (referral link) – 50,000 signup bonus (plus 5,000 for adding an authorized user)
American Express Starwood Preferred – 35,000 sign up bonus (special in February)
Capital One Venture – $400 sign up bonus redeemable for travel

Getting that Sweet Sign Up Bonus
All travel cards require that you hit a minimum spend to get the bonus which is usually around $3k or $4k in three months. I know this number can seem intimidating, but for us it wasn’t too bad. If you’re like my family and put EVERYTHING on your cards, averaging $1k a month on a card shouldn’t be too difficult. You could also prepay bills or buy a bunch of gift cards for stores you frequent, which in my case is Target and Costco. It also helps if you’re able to time big purchases after you sign up. For the Chase Sapphire we were able to put $3k towards the purchase of our new (used) car. 

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The Apple Pay of a credit card junky. Too bad Apple Pay is pretty useless.

Another method that some Travel Hackers use is Manufactured Spending, where you purchase Visa or Amex giftcards and convert them into money orders to deposit back into your bank accounts. It’s not something I’d recommend as it can be pretty time consuming and doesn’t always work. You’ll also get dinged on fees as these gift cards usually have a purchase fee of around $5 or $6 per card.

Converting Points to an Actual Flight
Figuring out how to actually convert those points I earned to a flight was definitely the most confusing part of travel hacking. The Chase Sapphire and American SPG cards are pretty versatile as you can transfer your points to many different frequent flier (and hotel) programs that these cards partner up with. These airlines also partner up with other airlines to give you that much more options. 

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Happy 40th Grandma and Grandpa

This happened to me when one of the flights going to Hawaii was American Airlines, which isn’t a direct partner of Chase or AMEX. After a bit of research and going back and forth with Michael, I found out that American Airlines was a partner with British Airways. Three round trip tickets to Hawaii would cost us 75,000 avios (points).

I transferred 35,000 points with Chase and 40,000 with my AMEX SPG to my newly created British Airways Executive Travel account.

I was then able to cover the $33 in taxes and fees from the points from my Capital One Venture card.

british airways quote

I got confused typing this so I’m sure if you’ve never even heard of travel hacking your head is spinning right now :). One thing that I’ve discovered in my first experience travel hacking is that you really have to plan out your trip a lot more than if you actually paid for it ;). Airlines only set a small amount of seats that can be redeemed for points so the availability is pretty limited. Our original plan was to have the trip from Sunday to Sunday, but there was nothing left when I looked. We had to settle for a Monday afternoon flight with a return flight on Saturday night.

So while we didn’t get the exact flights we wanted, we can’t complain that much because you know, it was still kinda free. 😉

What About My Credit Score?
The one question get from people the most when I talk about travel hacking (besides them telling me I’m crazy) is how is my credit score after all this madness. I’ve been travel hacking since the beginning of the year (and hoarding cash back credit cards for awhile) and my credit score has actually GONE UP. Last I checked my score was 825, which is for all intents and purposes perfect.

Credit 3.png

In my experience the two main things that have affected my score throughout the years is paying on time and having a low credit utilization. Since I have like 10+ active cards with pretty big credit limits, having all these cards helps keep my utilization low.

That being said, if you’re planning on buying a house or getting a car loan anytime soon, you’d probably want to stay away from Travel Hacking.

Travel Hacking Isn’t for Everybody. 
It takes a certain kind of crazy financial nerd to really get into travel hacking and score free and cheap travel. There’s a lot of cards you’d have to juggle and figuring out how to use points and miles effectively is a lot to wrap your head around. Most of the travel cards carry an annual fee (that’s usually waived the first year), which is something to keep in mind. Getting the bonuses in the first place can also be a challenge if you don’t spend too much on cards and would never consider manufacturing your spend. If you’re in debt, carry a balance on your card, or are just not a fan of using credit, travel hacking isn’t for you.

For those willing to put the time and effort, it’s worth it. I’ve only been doing this for a few months and have scored free hotel stays and even more free flights. I even found a way to Travel Hack Uber. I see more posts about Travel Hacking in this blog in the future. 🙂

I plan on taking my family to see the world. And if I have to sign up for a card or two (or twenty 🙂 ) along the way to make it happen, then I’ll be hacking away.

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29 thoughts on “How I Travel Hacked 3 Free Round Trip Tickets to Hawaii

  1. Wow. Congrats on the travel hack. That is pretty cool. You are right though, I noticed my credit score increase to the high 800+ when I kept my credit utilization low and paid my bills on time. Those two factors alone account for 65% of the weight of your credit score. Enjoy your trip to Hawaii!!

    Liked by 1 person

    1. Thanks Pamela! One of the flights is a red-eye so I don’t know how my daughter will do there. Hopefully she sleeps the whole way. Everyone thinks that my credit score must be garbage, but it’s stayed pretty high ever since I’ve been tracking it a year or so ago.

      Liked by 1 person

  2. Dude that is totally awesome. It’s inspired me to start digging in on what’s available to us up north 🙂 Well done!

    Liked by 1 person

  3. Glad I could help, Vic! It’s the rewarding part of running my site. Tell your parents that The Honeymoon Guy says congratulations on 40 years! 😉 Seriously – that’s impressive.

    You’re a Costco lover, too? Check out the
    post — — I published tonight on getting 5X points back with your Chase Freedom card at Costco (and BJ’s and Sam’s Club) for the rest of the year! Since you also have a Chase Sapphire Preferred those 5 points per dollar can be converted to Ultimate Rewards points. Those are worth about 2.1 cents each in my valuation, so you’ll effectively be getting a rebate of over 10% on your Costco purchases!

    -Michael, The Honeymoon Guy

    Liked by 1 person

    1. You’ve been a big help Michael – I greatly appreciate it!

      Thanks for the link – I’m already with you on the Chase Freedom card ;). Too bad Chase instituted their 5/24 rule. I wanted to get the Freedom Unlimited card but was ineligible. I was able to get a Chase Hyatt though.

      Liked by 1 person

    1. Since it can take awhile to hit the sign up bonuses, I’d recommend getting started as soon as possible! Then you’ll have points available when you’re ready :). I just signed up for a Chase Hyatt that has two free nights as the bonus. I’m not sure where we want to go yet, but we’ll be ready when that time comes :).

      I highly recommend getting a Chase Sapphire to start with. The sign up is worth $600+ worth of travel! More if you transfer to their partner airlines or hotels!

      Liked by 1 person

  4. Great travel hacks! I’m definitely going to be implementing this strategy right away. Thank you for sharing this amazing way for us to save money!

    Shared this on Facebook and Twitter too! 🙂


    1. That’s awesome Madison! I’d recommend to start with the Chase Sapphire first. It’s my favorite travel card :). With just that card I’ve gotten these Hawaii tix, a stay in San Diego, and another stay in San Luis Obispo!

      Liked by 1 person

    1. I was actually not much of a travel person myself. Mostly because of the cost haha. Once I started travel hacking, it’s encouraging my wife and I to look for more places to go! I just scored two free rooms on a Chase Hyatt and I’m not even sure what we’re going to do with it yet haha. But we’ll figure somewhere to go in the next few months. 🙂


  5. High five! I did 3 RT flights to SF to Hawaii ( for this spring but I decided to make it really simple and stick with United miles. One of my favorite options to have but haven’t really used is transferring my SPG points to airline miles – we end up redeeming our points for good hotel rooms most years.

    I need to pick our next cards for point accumulation soon!

    Liked by 1 person

    1. High five indeed! That’s awesome!

      One thing with the SPG points is that they take a few days to transfer, which can be killer if the open seats are unavailable by the time you can use the points.

      Let me know what cards you end up picking up!


  6. Wow! Sweet deal Vic 😀

    As I’ve been in the market for our first house the last year or so, so I haven’t been signing up for new credit cards that would affect my credit. 😦

    But I do think I’m cheap enough, organized enough and excited enough to look into travel hacking once we finally find our house 🙂

    I’m sure you’ll be doing this when you take your family to Asia. Write about it and I’ll read it xD (the flights were the worst and 4star hotels can be pricey – I wouldn’t mind learning how to get part of those covered at least via travel hacking).

    Liked by 1 person

  7. I really appreciate how you give such a clear explanation of what you did exactly and how much you saved. I started travel hacking a few years ago and, while i am not as hardcore as others, it has really allowed me and my family to expand our travel adventures while we are also trying to reach financial independence within a decade….

    Liked by 1 person

    1. that’s awesome! People look at me like I’m crazy when I tell them but I think of it as a few hours of work at most and you save a couple hundred bucks or more! I don’t think I’ll ever pay full price for travel again 🙂


      1. Totally agree! The only problem is that I am easily addicted to trying to find ‘the absolute best deal’ on miles/points so I need to just be ok with ‘great deal’ and move on lol.

        On my blog I am documenting vacation ideas for kids 0-4, 5-8, etc. as we take them and will try to post how much it would have been and how much they were actually with points. We are trying Hyatt Ziva Puerto Vallarta next – I am not doing full miles but for a large portion – but if you use Hyatt points you could do a week almost totally free since it is all inclusive!

        I am so coming back to this post when we are ready for Hawaii!

        Liked by 1 person

      2. That’s great! I look forward to checking out your blog.

        These tips don’t just work for Hawaii, it works for everywhere ;). I recently scored three free roundtrips from LA to Portland splitting the points between a Capital One Venture and a Barclay Arrival card.

        Liked by 1 person

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