HOW I TOOK MY FAMILY TO HAWAII FOR $44 USING POINTS
Four years ago, I booked my very first trip using points and miles. Since then, I've traveled the world, but every trip had one thing in common… I was mostly traveling solo or occasionally with friends.
This year was different.
For the first time ever, I used points to take my family on vacation.
Growing up, family vacations weren't something we could afford. My mother was low-income and raised four children as a single parent, so traveling together was never an option. As the oldest of four siblings, being able to create this experience for my family meant more than I can put into words.
This year was especially meaningful. My youngest sister graduated with her bachelor’s degree in nursing, my other sister celebrated her birthday, and my niece had never been on a plane before. She was so excited and wanted a window seat.
Instead of spending thousands of dollars on flights and hotels, we spent $44.80 out of pocket using points and travel credits.
Our Hawaii Trip at a Glance
Destination: Maui
Travelers: 4
Length of trip: 7 nights
Flights: 91,000 Southwest points + $44.80 in taxes
Hotels: 209,000 Hyatt points
Car Rental: $0 using Capital One travel credits
Cash value: $9,440.61
Total cash paid: $44.80
Seeing those numbers still amazes me.
Why We Chose Maui
Hawaii is one of my favorite destinations to recommend for families.
You don't need a passport, there are nonstop flights from many U.S cities, and there's something for everyone: beautiful beaches, snorkeling, whale watching (depending on the season), scenic drives, waterfalls, and incredible sunsets.
We decided on Maui because it offered the perfect mix of relaxation and adventure. We wanted time at the pools and beaches, but we also wanted to experience the famous Road to Hana and celebrate my sister's graduation and birthday somewhere unforgettable.
Flights
There are several ways to fly to Hawaii using points and miles through different airlines: United, Alaska Airlines, Hawaiian Airlines, American Airlines, and Delta.
For this trip, Southwest made the most sense since both my sister and I earned the Southwest Companion Pass, which allows one person to fly with you by paying only the taxes and fees whenever you book your ticket with cash or points. If you're interested in earning the Southwest Companion Pass, I break it all down in a separate blog post.
My sister and I each paid 45,500 points + $11.20 in taxes and fees per ticket. We then added our companions for just taxes and fees, bringing the total to 91,000 points for four people.
Cash Price WITHOUT points: $2,297.20
Hotels
Hotels are usually the most expensive part of a Hawaii vacation, but this is where Hyatt points really shine.
We stayed at two Hyatt properties for 209,000 points and $0 instead of $6,670.41.
Hyatt Regency Maui Resort & Spa
We spent six nights at the Hyatt Regency Maui in Ka'anapali.
I booked a room with two queen beds, which worked perfectly for the four of us.
The resort has multiple pools, direct beach access, wildlife throughout the property, and incredible sunset views.
Because we traveled during the summer, award nights cost 29,000 Hyatt points each. During off-peak dates, you can book this hotel for as little as 20,000 points per night.
One of the biggest benefits of booking Hyatt stays with points is that Hyatt waives resort fees on award stays, which can save hundreds of dollars.
Hyatt Hana-Maui Resort
Since we planned to drive the famous Road to Hana, we decided to spend one night at the Hyatt Hana-Maui Resort.
I'm so glad we did.
Instead of rushing back after a full day of driving, we were able to relax, enjoy the peaceful surroundings, and experience a completely different side of Maui.
This property cost 35,000 Hyatt points for one night, although award pricing starts at 25,000 points during off-peak dates.
The nightly rate, taxes, and resort fees for this property are INSANE!
Guest of Honor Benefits
One of the highlights of this trip was using a Hyatt Guest of Honor Award gifted by my friend who has Globalist Status with Hyatt. I used it at the Hyatt Regency Maui.
This gave us:
Free parking (valet parking is $55 per day and self-parking $50 per day)
Regency Club access with
Daily breakfast
Grab and go snacks
Evening appetizers
Desserts
Breakfast alone saved us hundreds of dollars.
Hawaii can be expensive, so having breakfast included every morning made a huge difference. Between breakfast, snacks, and complimentary parking, we saved over $700 during our stay.
If you're wondering how to book Hyatt hotels with points, I’ve written a full blog post that walks you through it step by step.
Car Rental: A Happy Accident
Last year my sister opened the Capital One Venture card when it offered 75,000 bonus miles plus a $250 Capital One Travel credit.
I booked our car rental last year to use the travel credit. We later changed our travel dates, and I couldn't modify the reservation. The only option was to cancel and rebook.
When we called Capital One Travel, we explained that her travel credit had already expired. Their customer service was amazing. They gave her back the credit and even increased it to $300.
Then something unexpected happened.
The system also refunded the original $250 credit, leaving us with $550 in travel credits!
I immediately rebooked our car rental. Total out-of-pocket cost? $0 instead of $473.
Even if that hadn't happened, we still could have covered this purchase using Capital One miles (47,300 miles = $473).
One of my favorite Capital One benefits is being able to redeem miles for any travel purchase made within the last 90 days. If you want to learn more about the Capital One Venture card, I break it all down in a separate blog post.
Total Cost Breakdown
Other Expenses
Points can't cover everything.
We still paid for food, snorkeling, a traditional luau, souvenirs, and a special graduation and birthday dinner.
Since our flights, hotels, and car rental were already covered, we were able to enjoy those experiences and splurge on other expenses.
That's the real power of points.
How We Earned Points
Planning a family vacation is very different from planning a trip for one person.
Since I needed enough points for four people, I started planning a year in advance. I had already been earning Chase Ultimate Rewards® points from credit cards I had opened over the years, but I knew I would need a lot more to cover flights and hotels for everyone.
Most of the points we earned for this trip came from credit card welcome offers, especially during elevated offers. These limited-time offers allow you to earn significantly more points than the standard offer (for example, 100,000 points instead of the usual 75,000).
While everyday spending on one credit card does earn points, the fastest way to build a huge stash of points is through welcome offers. You can often earn more points from opening one new card and meeting the minimum spend requirement than you would from months or even years of using the same card.
Chase offers several cards that earn Ultimate Rewards points. My sister and I strategically opened a few cards over the course of the year, allowing us to earn more than 350,000 points and miles.
Example Trip Strategy
If you're planning a trip to Hawaii with a friend, spouse, or family member, here's one example of how you can quickly earn a ton of Chase Ultimate Rewards® points when two people can apply for cards.
Player 1
Opens the Chase Sapphire Preferred® card and earns 75,000 points after meeting the minimum spend requirement
Refers Player 2 to the Chase Sapphire Preferred® card and earns 15,000 referral points once Player 2 is approved
Player 2
Opens the Chase Sapphire Preferred® card through Player 1's referral link and earns 75,000 points after meeting the minimum spend requirement
Total Points Earned
Together, you would earn at least 175,000 Chase Ultimate Rewards® points:
150,000 points from welcome offers
15,000 referral points for Player 1
At least 10,000 points from meeting the combined minimum spending requirements (assuming you earned 1 point per dollar)
That’s enough points to cover roughly 4–6 nights at Hyatt Regency Waikiki Beach Resort & Spa and/or 3–4 round-trip flights on Southwest to Oahu, depending on availability and travel dates.
If you decide to apply for this card, I truly appreciate if you use my referral link. It’s a great way to support the free content and resources I share. Thank you so much for your support!
Pro Tips
If you're planning your own Hawaii vacation using points, here's what I'd recommend:
Start earning points at least a year before your trip.
Open cards that earn flexible pointsso you can transfer them to multiple airlines.
Book flights as soon as award space becomes available.
Book a Hyatt property to save on resort fees
Earn the Southwest Companion Pass. It is a game changer for families.
Don't overlook benefits like Guest of Honor or travel credits (they can save hundreds beyond just flights and hotels)
Final Thoughts
Watching my niece look out the airplane window during her very first flight, recording the view, and taking it all in was one of my favorite parts of the trip. I also asked her what her favorite part of Hawaii was, and without hesitation she said, “the Hyatt.” I laughed because she was talking about the pools, having breakfast every morning, and then later mentioned snorkeling.
My other sister, who was also celebrating her birthday, flew for the first time too. She was scared but she did it! Seeing them experience all of this for the first time made the trip even more special.
At the end of the day, this trip reminded me why I love points and miles so much.
Yes, we saved over $9,000.
But the real value wasn’t the money... it was being able to give my family experiences we never had growing up and memories we’ll talk about for years.
If you’re just getting started, I hope this shows you that travel doesn’t have to come with a full price tag. With the right strategy and some planning, it’s possible to take trips like this for a fraction of the cost.
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