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How to Vacation to Hawaii for (Almost) Free with Travel Rewards

Matt Spillar

This post may contain affiliate links. Please read my disclosure for more information.

I’m sure you’ve seen some crazy headlines about travel floating around the Web:

“How to Take a Vacation to Disneyland for Free!”

“How We Traveled the World for Under $500”

Pretty bold claims. I started out dismissing them as clickbait – thinking it was too complicated and not worth the effort involved. It must be too good to be true, right?

Then my curiosity got the best of me. I started reading some of these articles to investigate the methods they were advocating. Most of the time they talked about redeeming miles or credit card points to purchase cheap flights around the world. Sources that I trusted were all saying the same thing – with a moderate amount of time and effort, travel rewards were the real deal!

I started getting into the world of travel rewards three years ago. During that time, we’ve accumulated over ONE MILLION points and miles and have enjoyed dozens of free flights. By far, our biggest win with travel rewards has been earning the Southwest Companion Pass twice!

I discovered for myself that these strategies DO work, and almost anyone can replicate it easily and inexpensively.

What are travel rewards?

If you haven’t read my introduction to travel rewards, I would highly recommended checking it out. Put simply, travel rewards are points and miles that you can earn from signing up and using certain credit cards. Some cards have lucrative signup bonuses, for meeting a minimum spending requirement within the first few months of owning the card (for example: a 50,000 point signup bonus for spending $3,000 within the first 3 months). You then can redeem these point or miles for nearly free flights and hotel nights.

Who is travel hacking for?

Travel hacking is for people who enjoy traveling and want to be able to do it less expensively. However, there are also a few key traits you should have before you consider whether travel hacking is right for you. You need to be well organized, have a good credit score, and have ZERO credit card debt. You NEED to pay off your balance in full every single month and not pay any credit card interest. If you’re unable to do this, do NOT bother with travel hacking yet.

Credit card debt is dangerous, and many people find they spend more money when paying with a credit card. The miles and rewards points only benefit you if you’re avoiding carrying a balance and paying interest. My wife and I have never paid a cent in credit card interest, and that’s the biggest factor why we’ve been able to benefit from travel rewards.

Our strategy for an (almost) free Hawaii vacation

Here’s how we’re taking a vacation to Maui for 8 days and 8 nights:

If we had paid cash for the entire trip, it would have been around $600 for the flights ($300 each), $940 for the first hotel, and $2340 for the second hotel for a total of $3880!!

So how did we accumulate these points?

Important details about this strategy

Chase Ultimate Rewards are extremely valuable because they can be transferred to various partners including: Southwest, British Airways, United, JetBlue, Hyatt, Marriott, among others.

With the two signup bonuses for the Southwest cards, plus some spending to reach 125,000 Rapid Rewards points, we unlocked the Southwest Companion Pass! The Southwest Companion Pass essentially acts as a Buy-One-Get-One free coupon. It allows the pass holder to take one designated companion on ANY Southwest flight they take, for the rest of the calendar year and all of the following year. For example, if you earn the pass in 2020, you would get to use this benefit for the rest of 2020 and ALL of 2021! It doesn’t matter if the flight is paid for with dollars or points, your companion flies free every time.

For more details about the Southwest Companion Pass, including the step-by-step process for how to earn it, check out this post.

The booking for the Kaanapali Beach Hotel was booked through the Chase Travel portal and the booking for the Westin Maui Resort & Spa was booked directly on Marriott’s website and selecting the “Use Points” option.

How to Replicate This Strategy

Now obviously, this trip took significant planning. We had to determine what cards to sign up for, meet the minimum spending requirements, space out those credit card applications to abide by the rules that Chase and American Express have, and the book the trip a few months in advance so that the flights and hotels were available. The payoff to this planing? A nearly $4,000 Hawaii vacation for free!

However, you don’t have to do exactly what we did to still enjoy an amazing Hawaii vacation. Here are just a few ways you could adjust this strategy to still end up with a similar result:

As you can see, there are many ways to make this happen for your own situation!

If I don’t have a business, can I still get a business credit card?

It goes without saying that your credit card applications need to be 100% truthful. Do NOT lie about having a business just to be approved. That being said, the definition of a small business is flexible when it comes to business credit cards. Your business needs to be legitimate, but it doesn’t need to earn a high income, or even any income, to qualify.

If you’ve been thinking of starting a business, but haven’t done so yet, it can still work. If you have no idea where to begin, think of a way that could earn side income.

For my business credit cards, I used this blog, as it earns some income and has various expenses associated with it.

Here are some examples of qualifying businesses:

If you have a well established business that makes a high income, use your employer identification number (EIN) on your credit card application. If you have a small business that makes a low income, use your social security number instead. It is common for small business owners to get a business credit card in order to keep their personal expenses and business expenses separate for tax purposes.

Rules to Keep in Mind

  1. Chase only approves new applicants that have signed up for less than 5 new credit cards (with any company) within the past 24 months. This rule is commonly called the 5/24 rule. If you are new to travel rewards, this probably won’t be an issue for you, but it’s something to keep in mind if you start signing up for additional cards. Business cards don’t add to this number, but you still need to be under 5/24 to apply for a new business card
  2. You can’t hold two Southwest personal cards or two Southwest business cards at the same time, only one of each.
  3. Avoid applying for more than one Chase personal card and one Chase business card within a 90-day period. When possible, apply for one card and then wait 30 days before applying for the other card. This helps maximize your chances of being approved.
  4. Avoid applying for more than 2 American Express cards within 90 days.

Remember that you are a customer and you want to cultivate a healthy long-term relationship with these banks. Don’t apply for too many cards too fast. Also, be sure to keep the accounts open and continue to use the cards whenever possible.

How Do I Get Started?

With getting started in travel rewards, it all depends on what type of trips you’re looking to take. Before applying for any credit cards, take some time to determine your strategy. Do you want to take the family to Disneyland? Fly business class to Japan? Take multiple trips within the United States? The type of travel you want to do will help define what strategy you should pursue.

For a vacation to Hawaii, the easiest way is to build up a stockpile Chase Ultimate Rewards  through the Chase Sapphire Preferred and Chase Ink Business Preferred. These can be used to cover accommodations at a wide variety of hotels, as well as flights on handful of different airlines.

If you want to stretch your Chase Ultimate Rewards further and take your vacation to the next level, you can apply for credit cards for a particular hotel brand and use those points instead.

Additionally, if you’d rather only have to pay for one flight instead of two, you can obtain the Southwest Companion Pass.

Final Thoughts

If you enjoy traveling and are diligent about paying off your credit card bills in full every month, it’s time to jump into the travel rewards world! Travel rewards are well worth putting some time and effort into learning about. By signing up strategically for a few different credit cards, you can piece together a once in a lifetime Hawaii vacation for (almost) free! Hopefully this post helped show you a few ways to make it happen. Take some time to develop a strategy, and I have no doubt you’ll be able to take the vacation of your dreams.

Feel free to comment or reach out to me with any questions, I’m happy to help!

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