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Hawaii is a dream destination! Everyone wants to go to Hawaii but most people think they cannot afford it. Well, I’m here to tell you that a trip to Hawaii can be cheap and nearly free just by using credit card points and miles. There are many strategies that people use to get to Hawaii with points, so I’ll explain a few of them here.

The average cost to travel to Hawaii for a family can be well over $5,000! We travel to Hawaii every year with our family of five without spending thousands of dollars. We usually use credit card points in some way to travel to Hawaii every year, either by flights hotels, or both. We go here every year as it is one of the best kid-friendly destinations because of the great activities, great resorts, and beautiful beaches!

If you’re brand new to points and miles, check out our beginner’s guide here!

Current Best Credit Card Offers Here

Use this step-by-step guide to learn how to book your next trip to Hawaii for free or nearly free!

How to start planning for Hawaii

Plan in advance

One thing to understand about booking with miles and points that many people don’t realize is that they need to plan in advance! Planning in advance means at least a year or more. You need time to get the cards and earn the points. Then you want to have your points in hand when the flight schedules and hotel schedules open up. This is the best way to get a high value and use the least amount of points possible.

Is it possible to book closer to your vacation date? Yes, it is possible, but hotel rooms bookable with points fill up fast, so you may end up using a travel portal to book hotels. If this is you, don’t be discouraged! You will still be saving plenty of money, but may not get the flight or hotel you want.

If you’re able to go off-season, then you will be able to use fewer points and money. The cheapest months to visit Hawaii are January/February or the fall months, like September or October. With flight prices on the rise in 2022, points and miles are the way to go!

Make a list of the best airlines to get you there

Take a look at your home airport and determine what airlines are flying to Hawaii from there. Which airline works best for you? For my family, Southwest flies out of Phoenix to Hawaii and that is usually the best airline for us to fly. However, I also have several options such as American Airlines or Hawaiian Airlines. They have several nonstops.

Keep in mind, that if you are flying from the West Coast, such as LAX, SAN, SFO, SJC, or PHX, your flights will be cheaper. Or you may need to take a look at a larger airport a few hours from you. For instance, we have flown out of San Diego, when we cannot find a good deal out of Phoenix.

You may be wondering how many Southwest points you will need to fly to Hawaii. Well, that number will vary a lot based on cost, but Southwest points are valued at 1.4 cents. Southwest miles program is tied directly to the cost of tickets. When prices were cheap, we were able to score a round-trip ticket from Phoenix to Kona for 12,000 Southwest points.

During Spring break, we had to pay around 35,000 points per round-trip ticket. When booking American Airlines through the Avios program, if you can find it available from the West Coast, you can book for as low as 16,000 miles each way per person.

To get an idea of how many points you will need, browse the airline websites and check the box to redeem points or book with miles. Keep in mind there are always sweet spots in points and miles when you use transfer partners. We discuss this option more below. This is a greater saving than booking with the airline directly. For instance, American Airlines will charge you over 20,000 points for a one-way, but when booked through the Avios program, it is only 16,000.

Another sweet spot for Hawaii flight redemptions is Turkish Airlines. You can book a United flight through Turkish Airlines. If available, you can find flights as low as 7,500 each way.

So as you can see the points vary a lot. So it’s good to take it step by step and figure out the best way to get there.

Recap: Determine how many points your family needs to fly the airline of your choice to Hawaii.

Find your ideal resort and island in Hawaii

Is there a resort that you have seen others stay at that is on your bucket list? If you don’t have a preference, look at Marriott, IHG, Hilton, and Hyatt’s Hawaii properties to get an idea of where you would like to stay. Pull up the points calendar on a desktop and get an idea of how many points it is for each night. Keep in mind, when booking with points, Marriott offers a 5th night free, IHG offers a 4th night free (with an IHG card), and Hilton offers a 5th night free (with status).

AC Wailea, a Marriott property in Maui, booked with 50,000 Marriott points

If you’re looking for the cheapest island to travel to, it will most likely be The Big Island. Flights and hotels to the Big Island tend to be cheaper.

If you’re looking for the most family-friendly island, really any of them are great! I do tend to prefer Maui and Kauai for our family vacations because of the great beaches and the number of great resorts.

Recap: Determine how many points your family needs to stay at the resort of your choice in Hawaii.

Key credit cards to get you to Hawaii

Here’s where the fun starts! Which card should you get first? Well if you’ve gone through the steps above and have a plan, then next you will need to find out what points will transfer to the partners that you need; and if you don’t have a plan, then start with the Chase Sapphire card. The offer on this card right now is 60,000 points after spending 4,000 on the card in three months and paying the annual fee of $95.

Let’s say for instance that you found Southwest Airlines to be the best way to get you to Hawaii. Then you need to figure out the best way to earn Southwest miles. Getting a Southwest credit card or getting a chase card would be the best ways to get Southwest miles.

Then perhaps you decided you wanted to stay at the Grand Hyatt in Kauai or maybe the Wailea Marriott in Maui. The best way to get Marriott points is through a Marriott co-branded credit card. The best way to earn Hyatt points is through a Hyatt co-branded card or a Chase card since you can transfer Chase points at a rate of 1:1 to Hyatt.

Recap: Based on the point type you need for Hawaii, determine which credit cards you will need to apply for. Make a plan.

Best hotels/resorts in Hawaii bookable with points

If you want to get a free hotel room or resort in Hawaii, these are the programs that you need to use! Below we have highlighted our favorite hotel from each point/miles system.

Hyatt points:

Grand Hyatt Kauai- This hotel is a favorite among points and miles enthusiasts. It is one of the best Hyatt redemptions in Hawaii. Book for as low as 25,000 points per night and it goes for over $1,000 in cash nightly.

Marriott Bonvoy:

Wailea Marriott- Another favorite of points and miles enthusiasts. We recently stayed here during Spring Break! My kids had a blast and loved all of the activities at this resort. We were able to book with 50,000 Marriott points, but those points needed will vary during season.

IHG Rewards

Holiday Inn Express Waikiki (we have not visited this property, but it is one of only two IHG properties in Hawaii) We would not recommend staying here for a long period but would work great for a short stay. Usually under 40,000 points per night.

Holiday Inn Express Waikiki, photo courtesy of IHG.com

Hilton Honors:

Grand Wailea, A Waldorf Hotel- one of the most luxurious resorts in Hawaii. You will want to add this one to your bucket list. You will need around 95,000 Hilton points a night here.

If you only have enough points for flights and not hotels, read about how our family saves money on hotels in Hawaii when we don’t use points. (see below)

Home rentals in Hawaii through Vacasa

By transferring points from Capital One or Citi to Wyndham’s Rewards, you can book a Vacasa Rental.

Vacasa Rentals are 15,000 points per night for a 0-1 Bedroom up to $350 (just changed from $500). Two bedrooms will go to 30,000 points per night. The sweet spot for points redemptions is definitely finding a one-bedroom that has a loft or a couple of extra rooms with beds that don’t count as bedrooms. Some of these one-bedrooms can sleep up to 8 people!

There is a great Vacasa home rental in Princeville, HI. Princeville is a perfect location for families to stay in because there are so many great beaches and it’s one of the most beautiful parts of Kauai.

At the Cliffs in Princeville, You can rent a unit at the Cliffs on Vacasa.com

Best flights to Hawaii bookable with miles

You might be asking, how many points do you need to fly to Hawaii? Well, each program varies, so here are some examples below:

Southwest Airlines

Southwest flight from Phoenix to Maui for 34, 528 points roundtrip

How to earn Southwest miles:

Earn Southwest miles through Chase cards or the Southwest Card. Here are our current favorites. And remember to maximize your points, after receiving your credit card by referring your spouse and they can get the same deal and you get referral points. Get my FREE guide to earning the Southwest Companion Pass HERE. The companion pass is one of the best strategies for a family flying to Hawaii.

Southwest Rapid Rewards Plus Credit Card

Southwest Performance Business Card

Chase Sapphire Preferred

Chase Sapphire Reserve

How to earn United miles:

Earn United miles with cobranded United Cards listed below. Or United is a transfer partner of Chase (a great reason to get the Chase Sapphire)

United Explorer Card

Chase United Quest Card

Sweet Spot

By transferring Capital One miles or Citi miles to Turkish Airlines, you can book a United flight through the Turkish Airlines Miles and Smiles program for around 7,500 each way per person. To be honest, availability is hard to find but can be done.

Capital One Venture Card

Capital One Venture X

Citi Premier Card

How to earn American Airlines miles:

Earn American miles with cobranded cards or you can transfer various hotel programs such as Marriott Bonvoy points at a 3:1 ratio to American Airlines miles (we don’t recommend doing that unless you are short a few points).

Here’s a great tip. With the Aviator personal MasterCard, you can earn the welcome bonus with just one purchase:

Barclays Advantage Aviator Mastercard

Barclays Advantage Aviator Business

Citi Advantage World Elite Mastercard

Citi Advantage Platinum Select World Elite Mastercard

Sweet Spot

Another way to book American Airlines flights is through the British Avios website. This is the sweet spot for Hawaii from the West Coast. Use Capital One , Membership Rewards, Citi points, or Chase Ultimate Rewards to transfer to British Avios. Remember to never transfer points until you have confirmed availability. (It is now 16,000 each way)

Booking American Via British Airways website

Only 13,000 (now 16,000) points when booking nonstop from the West Coast

Earning points to redeem on American flights continued…

Capital One Venture Card

Capital One Venture X

If you prefer, use your points in the travel portal:

These credit card travel portals are just like using a website like Kayak or Travelocity (you won’t always get the best value) but if you have a specific airline or don’t have the required miles for an airline, this may be a good option for you. Also, if the airfare is cheap to Hawaii, then booking through a travel portal can use fewer miles than booking with miles through an airline! Do the math and find the way to book with the least amount of miles.

How to book a Rental Car in Hawaii

It’s very easy to get around Hawaii by renting a car! If you want to book with points, then you can use a travel portal or a purchase eraser card like the Capital One Venture or Venture X.

If you are paying cash, then we would recommend Hawaii Discount Car rental. We have used this company to rent a Jeep Wrangler for nearly every year we travel to Hawaii. However, lately, the prices have gone up.

We love renting Jeep Wranglers in Hawaii

Last spring break we used wisecars, found on Kayak.com. We had to pay upfront but they had a free cancellation policy up until 48 hours before arrival, which worked great.

We have also used Costco to find good deals. Sometimes you may need to resort to Turo to find the best deal. We have had good and bad experiences with Turo.

You can also book a rental car through the travel portal if you are trying to save money. If you have enough miles, then it may be a great idea.

Tips for Beginners

If you are just starting out, here are some things to keep in mind:

Start with Chase cards. Since Chase has a 5/24 rule, you can only be approved for a Chase card if you have not applied for more than 5 new credit cards of any brand in the last 24 months. So fill up on Chase branded cards first if possible.

Start with cards that have limited-time deals or increased bonus offers. If you’re going to apply for a card, you want to be getting the highest amount of points if possible.

Refer your travel partner when possible to get those extra points! If you don’t have a link, we would love for you to use our links. It helps support our small business. Using our links is the same as using a direct bank link except we can earn a commission! We won’t know when you apply!

Give yourself time to meet your minimum spend and earn points. If your family is only two people, you may be going to Hawaii for free with just two credit cards or even one! However, the larger your family is, the more points you will need!

Download the FREE Travel Freely App to keep you organized.

Always reach out to us over on IG with questions! Just send us a DM. We love to help!

Enjoy Traveling Free!

How to vacation in Hawaii for nearly free with points and miles