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How to Use Points & Miles for a Free Family Vacation to Hawaii

How to Use Points & Miles for a Free Family Vacation to Hawaii

Most people love to go on holiday. After all, it's your time to unwind. But what if there was a way to go on a family vacay for free. I'm not talking about winning the lottery; I'm talking about using points to bankroll your next family adventure. And this adventure could be Hawaii. So, let's get started and see how you can use points and miles for a free family vacation to Hawaii. 


Using Points & Miles to Travel to Hawaii with the Family 

The first step you must take is to pack you bags. Okay, not yet. The first step is to plan ahead. Even if you're not new to travel hacking, you'll need a stockpile of points to make your Hawaiin holiday happen. So, planning six months to a year in advance is best. Even better if you have flexible dates for your trip. I'll get into that more later. 

Now that we've established that planning ahead is essential let's look at what credit cards you'll need to wrack up the points. 

Best Credit Cards to Use to Collect Points

There are a plethora of credit cards offering points and bonuses to choose from, but the beginner travel card that all the travel hackers recommend is the Chase Sapphire. 

Best Beginner Travel Card

The Chase Sapphire Preferred comes with a sweet sign-up bonus and lots of travel perks. Depending on different promotions, the sign-up bonus can range from 60,000 to 100,000 Ultimate Rewards Points. You earn this after spending $4K within three months.

Now, why should you sign up for Chase Sapphire rather than a United card (heck, you use this airline all the time)? But the value of "bank" points can surpass the airline points. 

Examples please (this is what you're saying!). 

Okay, Chase Sapphire has lots of travel partners (one of them is United). So those points can transfer to that partner, sometimes at a higher redemption value. Or you can transfer them to an airline or another hotel like Hyatt. 

But if you only earn United points, you can only use them for United flights. Chase points are flexible. You also can earn points through personal and business cards. You can choose from a few different ones, like the Ink Business Unlimited® card

Best Credit Card for Flights to Hawaii for Free

You may have a preferred airline, but one super nice way to fly to Hawaii for free is through Southwest. Southwest Airlines offers a complimentary companion pass for every member who earns 120,000 points in one calendar year. Now that may seem like a whole lotta points. However, it is possible even if you don't travel Southwest all the time. 

If you sign up for the Southwest Credit Card you can earn a sign-up bonus between 40,000 to 80,000 points. Southwest also offers different personal cards and business cards. Sign up for more than one and combine your points. Then, depending on when those bonuses hit, you can score a companion pass for 1 to 2 years. It’s best to go for the Southwest Companion pass 

Even if you don't earn enough points for a companion pass, you'll have enough points for a few free tickets. 

Chase 5/24 Rule 

One super important rule to keep in mind is the 5/24 rule. You can't apply for more than five Chase cards and other ones from certain banks and companies within two years. So if you have more than five cards, you won't be able to get another Chase card until after 24 months. 


If you are over 5/25, it's time to apply for the American Express Platinum. As a bank card, you can transfer points to many travel partners. It does come with a high annual fee, but if you take advantage of the benefits, you'll get your money back.  

Sometimes you can score a 150,000 sign up bonus. But if you'd rather have a lower annual fee, the Amex Gold card has a nice sign up bonus as well. You can then use those Amex points for flights to Hawaii or even for a family vacation in Thailand if that's what you prefer. 

Hawaii shores

How to Use Points & Miles for a Free Family Vacation to Hawaii

Remember when I said you need to plan ahead. This will really inform how you spend your travel points. Planning ahead means figuring out where, when, and how long you stay. For me, 7-days in Hawaii is a must, and if I can pull off 10, I'm in beach heaven

I prefer to stay close to the beach with a kitchen to make meals. Dining out in Hawaii can become pricey pretty quick. My hubby likes his space, so a condo-like atmosphere with a pool is the ticket. Achieving this is easy when you stay at a Hyatt properties You can reserve a one to three-bedroom with all the amenities. Plus, you can get all the hotel benefits too. 


Hyatt properties come in different classification levels from 1 to 6. One is on the cheaper end, and Class 6 is on the five-star level. Typically, Hyatt properties can range from $250 to $1,200 per night, depending on the class, size, and time of year.

So, if you know that you're going to stay 7-nights in Maui in October, and the points needed per night are 25,000, then you're going to need 175,000 points to make this possible.

But if you'd, find another property that's 15,000 per night, you only need 105,000 points. So, find the property you want first and determine the points you need. Hyatt shows the rewards calendar when you search, making it possible to see the points value for each option on the calendar. 

The same for flights.

Join Southwest and research how many points it would take to fly to Hawaii in your time frame. There are two things to remember about Southwest. First, they only publish flight options about six months in advance and love to run deals. What does this mean? You can book the flights and if they run the sale, cancel your flight and use the credit to book the lower flight.

Sometimes, you may have to book the hotel before the flight with points. But don't worry; if you follow the redemption guidelines, you can cancel before your points are gone. 

The Powering of Combining Credit Card Points

But you're probably thinking that a week-long vacation in Hawaii will take a few years to accrue in points. While this may seem like it's true, it isn't.

You're already ahead of the game if you time it right and get the right cards with good bonuses. But what can supercharge your travel hacking to a whole new level is to get a partner involved. In the travel hacking world, the spouse is referred to as the P2. But your travel partner can be your best friend, sister, or even your mom. 

How does this work?

Well, you get the Chase Sapphire Preferred with an 80K bonus, and then you refer your P2. Once approved, you get a 15K bonus for the referral. Your P2 then makes the minimum spend and gets the sign-up bonus. So you now have 175K in points between the two of you. 

You can do this for the Chase Southwest Card as well. You can even earn two companion cards between the two of you. When this happens, each of you can take a kid for free.

Travel hacking may seem like a holiday for wealthy people, it isn't. With a little planning and getting the right cards, you can use points and miles for a free family vacation to Hawaii. Or any other travel destination you desire. I will warn you though, once you start travel hacking, it will be really hard to stop. Free travel is better than free pizza, no matter who you ask. 

I'd love to hear about your travel hacking successes below. Leave a comment and tell me how it's going. In the meantime, join our community and receive a discount on your next beach bag. 

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