How I Used Half a Million Points for a 9-Night Family Trip to Hawaii

Taking my family of 5 to Hawaii is the kind of trip most people dream about — but the price tag can be intimidating.

A 10-day vacation with flights and top hotels for all 5 of us can easily cost over $10,000. That’s a lot, even for a family that travels often. However, with careful planning, smart use of points and miles, and strategic leveraging of welcome bonus offers, we made it happen comfortably — without breaking the bank.

In this piece, I’ll walk you through exactly how we booked the trip, how we accrued and transferred points over time, and why a long-term strategy is the key to making a Hawaii vacation doable with points and miles.

Booking 5 Flights to Hawaii (138K Points)

Flying to Hawaii is typically the most expensive part of the trip. With 5 people, finding award availability can feel daunting. For this trip, I focused on securing flights that worked best for our family, prioritizing an optimal flight schedule over business class awards to make the long travel day easier for our 3-year-old daughter.

I was strategic about how I earned and redeemed points and followed our guide on the best ways to fly to Hawaii with points.

1. Phoenix (PHX) to Maui (OGG)

Points used: 87,500 Atmos Rewards points
Cash equivalent saved: $1,659
Value per point: 1.9 cents per point

I always start by locking in the West Coast-to-Hawaii flights first, only then worrying about how to get there from South Florida. For this trip, I found award seats from Phoenix to Maui on American Airlines and booked them using Alaska Airlines Atmos Rewards points.

In my experience, Alaska Airlines offers some of the best redemption value for Hawaii routes, with award rates starting at just 9,000 points and $5.60 one-way — often far lower than competitor pricing.

This is where years of planning and strategic points accumulation paid off. I’d been building a stash of Alaska points over time by opening a few Alaska Airlines co-branded credit cards and taking advantage of transfer opportunities when they were available. I even took advantage of the ability to transfer American Express Membership Rewards to HawaiianMiles and then over to Alaska — a clever trick before that loophole closed this past summer.

More recently, I topped off my balance with the Atmos™ Rewards Summit Visa Infinite^® card, which came with a 100,000-point welcome bonus offer when I applied for it.

Having that cushion of points ready to go made all the difference. Without them, these flights would have cost more than $1,600 for the 5 of us.

Instead, I booked all 5 seats by redeeming 17,500 Alaska Atmos Rewards points per person and $19 in taxes for direct American Airlines flights from Phoenix to Maui — saving thousands and giving our family a much smoother way to get to Hawaii.

We value Alaska Atmos Rewards points at 1.6 cents per point, making this an excellent redemption that got our family to Hawaii for far less than paying cash.

2. Fort Lauderdale (FLL) to Phoenix (PHX)

Points used: 50,100 JetBlue TrueBlue points
Cash equivalent saved: $733
Value per point: 1.4 cents per point

To position us for the flight to Hawaii, we first needed to get to Phoenix. For that, I used JetBlue TrueBlue points earned from the welcome offer from The JetBlue Plus Card that my wife opened a few months ago.

She earned an 80,000-point welcome bonus offer, and this card has been one of my favorite tools for short domestic trips because the points are easy to earn and JetBlue offers consistent availability across the U.S.

For this leg, I found a Fort Lauderdale (FLL)-to-Phoenix JetBlue flight that was a perfect fit for our schedule and happened to be cheaper than flying out of Miami (MIA).

The out-of-pocket cost was just $146 per person. Using points was a wise decision, as paying cash for 5 domestic tickets can quickly add up, particularly during the high-demand spring-break dates.

What’s great about The JetBlue Plus card is that its points are straightforward to earn through everyday spending.

We ended up getting a solid 1.4 cent per value redemption rate. JetBlue TrueBlue points are tied to revenue pricing, which means you don’t get outsize value like you can with some other programs. That said, they can work amazingly well for positioning flights — especially if you live in a city with JetBlue service. Use them strategically to get to a hub for your long-haul award without breaking the bank.

Hot Tip:

If you’re traveling to Hawaii from the East Coast with kids in tow, don’t try to do it all in a single day. I favor a one-stop flight to a West Coast city with an overnight stay to break up the journey. It makes the trip more manageable, keeps everyone in better spirits, and avoids the brutal 15-hour-or-longer marathon from the East Coast to Hawaii.

Booking 9 Hotel Nights in Hawaii (264K Points)

Points used: 264,000 World of Hyatt points
Cash equivalent saved: ~$6,000
Value per point: 2.2 cents per point

This is where the trip gets very expensive if it weren’t for points. Now that I was able to get all of us to Hawaii on a flight itinerary that works for everyone, our next priority was finding a place that could comfortably accommodate our family while also offering perks to maximize value.

We chose 9 nights split between the Andaz Maui at Wailea Resort and the Hyatt Regency Maui Resort and Spa in Kaanapali.

Both hotels are longtime favorites — we’ve stayed at them before and love the service, pools, and convenient locations. However, these hotels are notoriously difficult to find award availability for, especially during peak travel dates like spring break.

Luckily, I like to book travel well in advance, and about 10 months prior, I was able to secure award nights at the Hyatt Regency Maui for 21,000 points per night for our 5-night stay, while cash rates for a standard room were starting around $500 per night. That’s well over 2 cents per point, significantly higher than our 1.5 cents per point valuation of Hyatt points.

I also added a Suite Upgrade Award to nab a suite, thanks to my World of Hyatt Globalist elite status. Looking now, several months later, the Ocean View Suite we were preassigned is costing more than $2,000 for our dates. This is why I’m a firm believer that with high-demand hotels, the early bird gets the worm.

The Andaz Maui, however, is a much bigger challenge. This luxury hotel is incredibly tough to book with points, as consecutive nights aren’t always available. Thankfully, I set up an alert with MaxMyPoints for our 4-night stay, and months later, I received a text alert stating that standard award nights had become available — perfect timing for our trip.

The Andaz Maui is a Category 8 World of Hyatt property, which places it at the top of Hyatt’s award chart. Therefore, I redeemed 45,000 points per night for a total of 180,000 points for our 4-night stay by transferring Chase Ultimate Rewards points to cover the booking. Given that a standard 2-queen room would have cost more than $900 per night in cash, this redemption provided exceptional value.

Additionally, as a World of Hyatt Globalist, I will enjoy perks such as lounge access, complimentary breakfast, and room upgrades, which add significant value and savings. For a family of 5, breakfast alone at these resorts can easily run $100 to $150 per day, so these benefits not only make the trip more comfortable but also save me a big chunk of cash.

Instead of paying over $6,000 for 9 nights, I used Chase Ultimate Rewards points transferred at a 1:1 rate to World of Hyatt. These points were accumulated over time through my Chase Sapphire Preferred^® Card, Ink Business Preferred^® Credit Card, Chase Freedom Flex^®, and The World of Hyatt Credit Card, providing me with a pool of points that I could strategically deploy for high-value stays.

I’m calculating my savings conservatively, but if you factor in what the suite we upgraded to would have cost at the Hyatt Regency Maui, the savings come out to around $10,000 just for the 5-night stay. That said, I would never have paid that in cash, so I’m not inflating the actual amount saved.

Still, staying at these highly acclaimed hotels in Maui with my family and using points to offset the costs was a key part of my strategy for planning this trip.

Booking 5 Flights Back Home (143K Points)

As much as we won’t want to leave Hawaii, we’ll eventually have to make our way back home. I always plan one-way awards when organizing big trips like this — it gives me far more flexibility to piece together the best flights using different airlines and programs.

This approach allows me to use points and miles based on what works best for our schedule, rather than being tied to a single carrier or a round-trip itinerary.

1. Maui (OGG) to Las Vegas (LAS)

Points used: 87,500 Atmos Rewards points
Cash equivalent saved: $1,600
Value per point: 1.8 cents per point

This strategy paid off again on the return, as the best award rates I found were through Atmos Rewards, which offered an excellent redemption from Maui to Las Vegas for just 17,500 points per person. Among all the West Coast options, Las Vegas had enough award space for our family of 5, and the 11:25 a.m. departure made for an easy, relaxed morning flight.

Considering cash fares were over $400 per person, saving more than $1,600 on the first leg of our journey home felt like a big win.

2. Las Vegas (LAS) to Miami (MIA)

Points used: 55,000 American Airlines AAdvantage miles
Cash equivalent saved: $1,250
Value per point: 2.2 cents per mile

Finally, we’ll fly home from Las Vegas to Miami by redeeming American Airlines AAdvantage miles. Over the years, my wife and I have built a strong balance of AA miles through frequent flying on American from Miami, one of our hometown airports, and our use of American Airlines co-branded cards. This was the perfect opportunity to put them to use.

I was able to book this flight for 11,000 miles and $5.60 per person, which saved us $1,250 total.

I usually value AAdvantage miles at 1.4 cents each, so getting 2.2 cents per mile here was a sweet win.

Hot Tip:

The biggest takeaway? Diversify your points and don’t rely on a single rewards program. Spread points across Chase, American Express, Alaska, and airline-specific programs to give yourself flexibility. Also, remember to book early, especially for Hawaii, as award space tends to disappear quickly.

Final Thoughts

A Hawaiian vacation for a family of 5 doesn’t have to cost a fortune. By planning ahead, stacking points across multiple programs, and timing redemptions carefully, we saved well over $10,000 while staying at incredible hotels and creating memories that will last a lifetime. Every mile, every point, and every transfer mattered — and with a little strategy, your dream Hawaii trip isn’t just possible, it’s within reach.