Booking a trip to Hawaii is almost a rite of passage for points and miles people; it’s an aspirational destination that usually comes with a correspondingly high price tag. Unsurprisingly, it’s a popular points and miles destination, because you can get some incredible value for your points! Here’s how we’re doing it. 

Flights & Hotels for 3 Passengers	Cash Price	Points Paid	Out of Pocket Cost
Flight: Raleigh, NC to Santa Ana, CA	?	?	?
Flight: Long Beach, CA to Maui, HI	$711	52,500	$16.80
Hotel: Hyatt Regency Maui	$4,267.70	145,000	$0
Flight: Maui, HI to New Yok, NY	$7,167	150,000	$1,550
Flight: New York, NY to Raleigh, NC	$447	17,000	$16.80
Grand totals	$12,592.70	364,500	$1,583.60

Hotel

The Grand Hyatt Kauai and the Hyatt Regency Maui are the two most talked-about Hyatts on the islands; however, the Grand Hyatt Kauai is now a category 8, which means that a night in peak season will set you back 45,000 points. Yikes!

By contrast, the Hyatt Regency Maui was downgraded this year to a more approachable category 6, with a peak price of 29,000 points per night. This is likely due to the decline in tourism generally after the Maui wildfires of 2023. I booked five nights at this property for a grand total of 145,000 points transferred from Chase Ultimate Rewards. The cash price for this room would have been $4,267.70, yielding a satisfying 2.9 cents per point in value.

Although there’s no way to know for sure, there is widespread speculation that this hotel will return to category 7 in the next year or two, so if you want to take advantage of its current pricing, you should plan to book your trip before Hyatt’s annual recategorization at the end of March.

Flights

Although I built this trip around the hotel, it’s an airline redemption that I’m most proud of. We are based in Raleigh, and Hawaii is a LONG way from here. Many flights back to the mainland US are red-eyes, and add in the fact that I’ll be traveling with two young children…it’s a recipe for misery. So I started with our flights home, and focused on making that leg of the trip as comfortable as possible. Lie-flat seats between Hawaii and the East Coast are notoriously hard to book, but for travelers who are willing to spend a little cash as well as points, there is a way–for a little bit longer, at least. 

Until September 26th, 2025, Hawaiian Airlines allows travelers to use points to upgrade cash tickets from economy to first class. The “saver” level price for this upgrade is a flat 25,000 points per leg, while the “flex” level upgrade is 50,000 points (Hawaiian miles are now Atmos points, thanks to their merger with Alaska). Obviously the saver level upgrades are a screaming deal, but as we are traveling during peak season, I knew that we were unlikely to find this, so I was prepared to pay the flex price.  I have a stash of Atmos points that I transferred over from American Express earlier this year, when that was still possible, with this trip in mind.

I used a tool called Expert Flyer to monitor award space for these upgrades. You input your route, dates, and airline, and you check boxes to indicate whether you want to see saver awards, flex awards, or both:

The results screen includes one tab per date indicating the number of upgrade awards available for each category. This step was important because I didn’t want to buy a cash ticket, only to learn that there were no upgrades available for that flight.

Once I confirmed that upgrade space was available, I bought my cash tickets, then immediately called Hawaiian to perform the upgrade.

In the end, I spent $517 and 50,000 points per ticket to travel from Maui to New York, including a 45-minute island hopper flight to Honolulu and the 10-hour long haul overnight flight from Honolulu to JFK. The cash price for this ticket would have been $2,539, so if we subtract the $517 I paid in cash, I’m getting 3.7 cents per point in value. 

One rule of thumb to evaluate pricing for lie-flat seats is that it’s reasonable to spend either 10,000 points per hour of flight time, or $100 per hour if you’re upgrading with cash. The way I think about this flight is I paid $100 per hour for five of those hours, and 10,000 points per hour for the other five. 

Since I was able to secure the three seats I needed, on the exact dates that I needed, during peak season, I’m happy with this.

Here’s how I booked the rest of our flights for this trip:

• RDU to the west coast: I haven’t actually booked these yet! I expect I will once Southwest opens their schedule, since we have a companion pass. We will spend a few days in Southern California, visiting family and adjusting to the time change. (This is one thing about award travel that can take some getting used to–sometimes you book trips in stages rather than all at once.)
• Long Beach to Maui: Booked on Hawaiian for 17,500 Atmos points per person. (Cash price: $237 per person.) At 1.3 cents per point, it’s not my best redemption, but I didn’t want to pay cash, since I already paid a considerable amount for our long haul flight home.
• The Maui to JFK leg comes next. We’ll spend a few days with my in-laws in New York, since we’re there.
• JFK to RDU: Booked on Delta via Virgin Atlantic (more about that trick here) using points transferred from Capital One with a 30% transfer bonus; 5,700 Capital One miles per person. 2.5 cents per point, not bad for a short domestic flight! (Cash price $149 per person.)

Steal This Trip

All told, we’re paying about 13% of the retail price for this trip, and getting over $10,000 worth of value from our points. Because of the cost and distance, this is a trip we never would have undertaken without points. Here are some tips if you’re looking to replicate this trip, or just leverage some of the techniques I used:

• Be opportunistic. Chase the deal (like a hotel that’s dropped a category), not the destination.
• Plan ahead, and try to book your travel right when the schedule opens.
• Hawaiian upgrades with points are going away on September 26th, 2025, but consider how your cash budget and your points can work together. Sometimes this means buying an award ticket and upgrading with cash. Sometimes this means buying points.

If Hawaii is on your radar, consider picking up one of the elevated offers on the Chase Ink Business cards to cover a Hyatt hotel stay. Although I usually recommend earning transferable points over airline-specific points, a Hawaiian card might also make sense in this case.

Watch this space for a full trip report next summer!