How We Planned Our Hawaii Family Vacation for Almost Free — And How You Can, Too!

A Dream Hawaii Family Vacation for Just $67.20

Aloha! If you’ve been dreaming about taking a Hawaii family vacation but feel held back by the cost, I’ve got great news: you can make that dream a reality by using points and miles! My family traveled to Hawaii this year, visiting both Oahu and Maui, for an unbelievable grand total of only $67.20 in taxes and fees. Yes, you read that right!

In this guide, I’ll share exactly how we did it and how you can plan your own nearly free Hawaii family vacation. From earning points to booking flights and accommodations, I’ve got all the tips to help your family escape to paradise on a budget.

Why Hawaii on Points and Miles Is Worth It

A Hawaiian vacation is often considered a once-in-a-lifetime trip, but with points and miles, you can make it a regular part of your family’s travel plans. By leveraging the right credit cards, earning bonuses, and booking strategically, you’ll be on your way to enjoying the Aloha State without breaking the bank.

Hawaii offers something for everyone: pristine beaches, lush landscapes, and a unique culture that’s both relaxing and enriching. Knowing our trip only cost $67.20 made the sunsets even more beautiful and the memories even sweeter.

How We Did It: Our Step-by-Step Strategy

Flights: Southwest Companion Pass and Flexible Points

We flew Southwest Airlines, taking full advantage of the Southwest Companion Pass—a game-changer for families. Both my husband and I earned Companion Passes, allowing our two boys to fly free (plus taxes and fees) on every flight. For our roundtrip journey, we paid just $67.20 in taxes and fees. It broke down as $5.60 in taxes and fees per person per flight. We flew one leg from the mainland US to Oahu, then Oahu to Maui, then Maui home.

To cover the rest of the ticket costs, we used a combination of:

• Southwest points earned while working toward our Companion Passes.
• Chase Ultimate Rewards points, transferred to Southwest.

Accommodations: Hyatt Points for Family-Friendly Stays

Maui: Wailea Ekahi Village Condos

On Maui, we stayed at the Wailea Ekahi Village condos through Hyatt’s Homes & Hideaways program. This was a highlight of our trip for so many reasons:

• Space and Comfort: Our two-bedroom condo included a full kitchen, laundry facilities, and plenty of room for six people.
• Family-Friendly Amenities: The property featured multiple pools, lush gardens, and easy beach access.
• Convenience: Having a kitchen allowed us to prepare meals, saving money on dining out, and the laundry facilities made packing light a breeze.

Oahu: Hyatt Place Waikiki Beach

We stayed at the Hyatt Place Waikiki Beach for our Hawaii family vacation, a fantastic choice for families. Here’s why:

• Room Size: Spacious enough to sleep up to six, perfect for larger families.
• Free Breakfast: A hot breakfast buffet each morning helped us fuel up for busy days. The boys absolutely love the breakfast buffet at Hyatt Places.
• Location: Just a short walk to Waikiki Beach and close to family-friendly attractions like the Honolulu Zoo and Waikiki Aquarium.
• Affordable Points Redemption: We used points from the World of Hyatt personal credit card and Chase Ultimate Rewards, making this stay budget-friendly.

How Your Family Can Do It, Too

Step 1: Choose Your Points Strategy

Depending on your travel style and current credit cards, here are some potential strategies for your Hawaii family vacation:

Flights

• Southwest Airlines:
  • Earn the Companion Pass by opening two Southwest credit cards (business and personal) and meeting the minimum spend, making sure the points earned is at least 135,000 in a calendar year.
  • Transfer Chase Ultimate Rewards points to Southwest.
• Other Airlines to Hawaii:
  • Alaska Airlines: Earn points through their credit cards or transfer Marriott Bonvoy points to Alaska Mileage Plan.
  • Delta Air Lines: Earn points through Amex Membership Rewards cards or book directly with Delta SkyMiles.
  • United Airlines: Transfer Chase Ultimate Rewards points or earn points through United credit cards.

Hotels

• Hyatt: Use Chase Ultimate Rewards or Hyatt points to book family-friendly properties like:
  • Hyatt Regency Maui Resort and Spa: This luxury resort offers a variety of family-friendly activities, including a water park, lei-making classes, and nightly luaus. Its beachfront location and lush grounds make it an ideal choice for families.
  • Hyatt Centric Waikiki Beach: Located in the heart of Waikiki, this property combines modern amenities with convenience. Families will appreciate its proximity to dining, shopping, and beaches, as well as the spacious rooms.
• Other Family-Friendly Hotel Options:
  • Hilton: Earn points with Hilton Honors credit cards or transfer Amex Membership Rewards. Properties like Hilton Hawaiian Village Waikiki Beach Resort offer extensive kid-friendly activities.
  • Marriott: Use Marriott Bonvoy points for properties like the Marriott’s Ko Olina Beach Club on Oahu. Both Chase Ultimate Rewards and American Express Membership Rewards allow point transfers to Marriott Bonvoy.
  • IHG: Earn points with IHG credit cards for resorts like Holiday Inn Resort Waikiki Beachcomber. For IHG One Rewards, Chase Ultimate Rewards does not transfer to IHG directly, but you can earn IHG points through co-branded IHG credit cards issued by Chase.

Step 2: Earn Points Strategically

To turn your Hawaii family vacation into a reality, you’ll need to earn points strategically. By selecting the right credit cards and optimizing your spending, you can accumulate the points needed for flights, hotels, and even extras. Here’s how:

Chase Ultimate Rewards

Chase Ultimate Rewards is one of the most versatile points programs, offering the ability to transfer points to travel partners like Southwest and Hyatt.

• Best Cards to Use: The Chase Sapphire Preferred, Chase Sapphire Reserve, and Ink Business Preferred cards are excellent options for earning points.
• How to Earn Points: Use these cards for everyday spending, especially in bonus categories like dining and travel. For instance, the Sapphire Preferred earns 2x points on travel and dining, and the Sapphire Reserve earns 3x points.
• Why It’s Great for Families: Flexible points mean you can decide later whether to transfer them to airlines like Southwest or hotel programs like Hyatt based on your travel needs.

Co-Branded Credit Cards

If you have a specific travel goal in mind, co-branded credit cards can help you fast-track your points accumulation.

• Southwest Rapid Rewards Cards: These cards can help you earn the Southwest Companion Pass quickly, a game-changer for family travel.
• Other Airline Credit Cards: Co-branded airline credit cards can also help you earn miles for flights to Hawaii. Here are a few great options:
  • Alaska Airlines Visa® Signature Card: This card offers a generous welcome bonus, 3x miles on Alaska purchases, and the Companion Fare benefit, which allows a second ticket for just $99 plus taxes and fees. Alaska Airlines acquired Hawaiian Airlines in September 2024, which is why it’s now a top option for flying to Hawaii.
  • Delta SkyMiles® Gold American Express Card: Earn a substantial welcome bonus, 2x miles on dining and Delta purchases, and enjoy perks like a free checked bag and priority boarding.
  • United Explorer Card: This card offers a strong welcome bonus, 2x miles on dining, hotel stays, and United purchases, and valuable travel benefits like free checked bags and priority boarding. Chase Ultimate Rewards points can also be transferred to United, giving you even more flexibility.
• Hyatt Credit Cards: The World of Hyatt personal or business credit cards come with bonus points, free night certificates, and accelerated point earnings on Hyatt stays.
• Other Hotel Options: Hilton Honors, Marriott Bonvoy, and IHG credit cards often feature generous welcome offers that boost your points balance. Here are some great card options to consider:
  • Hilton Honors: The Hilton Honors American Express Surpass® Card offers strong earning potential on Hilton stays and everyday spending, plus complimentary Gold status, which includes perks like free breakfast.
  • Marriott Bonvoy: The Marriott Bonvoy Boundless® Credit Card from Chase provides a large welcome bonus, automatic Silver Elite status, and 6x points per dollar on Marriott purchases.
  • IHG: The IHG® Rewards Premier Credit Card offers a significant signup bonus, 5x points on IHG stays, and an annual free night certificate, making it a solid choice for family travel.

Signup Bonuses

Signup bonuses are one of the fastest ways to earn a large number of points.

• Be Strategic: Watch for elevated offers on key cards, like 60,000 or more Ultimate Rewards points for the Chase Sapphire Preferred. These offers can cover multiple nights at hotels or a significant portion of your flights.
• Timing Matters: If you’re planning a big trip like a family getaway to Hawaii, aim to open new cards and meet the minimum spend requirements several months in advance.

By combining everyday spending with strategic use of signup bonuses and co-branded credit cards, you’ll be well on your way to a nearly free Hawaiian vacation.

• Chase Ultimate Rewards:
  • Cards: Chase Sapphire Preferred, Sapphire Reserve, or Ink Business Preferred.
  • Use for everyday spending to rack up transferable points.
• Co-Branded Credit Cards:
  • Southwest, Hyatt, Hilton, or Marriott cards can accelerate your points earning.
• Bonus Offers: Keep an eye out for signup bonuses to jumpstart your points balance.

Step 3: Maximize Your Redemptions

• Airline Tickets: Book early to find award availability, especially for flights to Hawaii during peak seasons.
• Hotels: Look for family-friendly properties with good redemption value. Some Hyatt properties, for example, start as low as 12,000 points per night.
• Condos and Villas: Consider options like Hyatt’s Homes & Hideaways for larger accommodations with kitchens and laundry.

Other Tips for Planning Your Hawaii Family Vacation

• Island Hopping: Southwest also offers inter-island flights, which can be booked with points.
• Car Rentals: Use credit card perks or points for discounts and savings.
• Local Activities: Many credit cards offer travel credits or perks that can be applied to excursions, like luaus or snorkeling trips.
• Listen to This Podcast: I shared our tips and tricks on the Wonderland on Points Podcast. Listen here.

Now it’s your turn! Start planning, start earning, and say Aloha to paradise.

If you want to start planning your Hawaii Family Vacation, you can read this 5 Fun Must Do in Oahu with Kids.

Pin this for later if you’re inspired to plan your family’s Hawaiian getaway on points and miles!

If you have any questions or need further advice feel free to email me or send me a message on Instagram. I’m always happy to share more tips and insights to help you.

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