Trip Information

Reader Shelia’s looking to take the whole family to Hawaii in May. That’s six adults total, heading from Charlotte (Knoxville, TN or Greensboro, NC would be other departure options she’d consider). They’d like to spend a day in Oahu to see the Pearl Harbor Museum and Battleship Missouri Memorial and then head on to Maui for another four or five days. If possible, they’d like to have a stopover in San Francisco on the way. Shelia’s looking to travel sometime between May 24th and Mid-June for a total of 7 days.

Current Program Status

Shelia’s coming into this trip with a truckload of points in various programs. In total, she has:

• 100,000 American AAdvantage Miles
• 100,000 United MileagePlus Miles
• 145,000 Ultimate Rewards Points
• 2 Free Nights at Any Hyatt
• 2 Free Weekend Nights with Hilton
• 25,000 Starwood Preferred Group Points
• 45,000 Priority Club Points

She’s also ready and willing to consider any travel credit cards that might help her towards her goal, but we’ll try to work within the framework of what she has already.

Our Take

The good news is, Shelia has a veritable pile of miles and points to work with. The bad news is, finding awards for six passengers is tough! It’s even harder when heading to a popular destination like Hawaii. To make this work, we’ll need to be clever, and Shelia’s traveling party will need to be flexible. Still, where there’s a will, there’s a way. Let’s get started!

Getting There

Shelia had mentioned a desire to stop in San Francisco for a day along the way in order to break up the trip. This would only be possible on a United roundtrip booking, as award rules for United only allow a stopover on roundtrip journeys and award rules for American only allow a stopover on international flights at an international gateway city. As Shelia and her family would be flying from San Francisco to Honolulu, San Francisco wouldn’t count as a valid stopover.

Booking a roundtrip for 6 people on United is beyond even the reach of Shelia’s extensive points balances but more importantly, there’s simply no availability for a party of that size out of any of Shelia’s potential departure airports during her time window. Take a look at this calendar of availability from Charlotte to Honolulu for six passengers, for example:

While there’s a smattering of availability in early May, the calendar dries up totally later on. We’ll have to surrender the San Francisco stopover toward the greater good of simply getting everyone to the final destination in this case.

Incredibly, there’s precisely one itinerary available presently from American that would fit the bill for all six of Shelia’s passengers to fly together.

This ugly routing takes advantage of the new ability to book US Air flights using AAdvantage miles as part of the ongoing merger process between US Air and American. Shelia’s family would fly from Charlotte to Miami on US Air, take an American flight from Miami to Las Vegas, then board a redeye from Vegas to Honolulu, arriving early the next morning.

To book this itinerary, Shelia would need 135,000 AAdvantage miles. That’s more than she has, so it’s worth considering exactly how good of a deal this is before taking some drastic measures to up her miles count quickly.

The cheapest cash fare we could find for the same day is an even uglier routing available via Alaska Air that takes over 26 hours of travel time for $460 each:

The first itinerary taking less than 20 hours comes in at $573 per person. As such, this American award is a pretty darn good grab. While 20,000 of the 22,500 miles per person required for this ticket could be applied to off-peak travel to Europe, Charlotte to Honolulu is actually a farther journey than Charlotte to London would be, so it’s hard to feel too bad about that!

Given Shelia’s in need of 35,000 more AAdvantage miles right away and there’s not time to wait on a credit card bonus to come through, she has a few options:

Transfer from SPG

One of the greatest perks of the Starwood Preferred Group program is its exceptionally versatile list of transfer partners and the transfer bonus it offers. For every 20,000 Starpoints transferred out to a partner program, SPG provides a bonus of 5,000 more. That means 20,000 Starpoints can become 25,000 AAdvantage miles.

That will wipe most of Shelia’s SPG balance, but in the service of a good cause. She could transfer all 25,000 SPG points for a total of 30,000 AAdvantage miles if she’d like, or 20,000 SPG points for 25,000 AAdvantage miles. We’ll assume she empties the account, leaving her only 5,000 AAdvantage miles from her goal.

Transfer from Priority Club

IHG’s program also allows for transfer of points to airlines, but at a much more disadvantageous rate. 10,000 points with Priority Club become a mere 2,000 American miles. This is hard to recommend as an option accordingly.

Buy Miles from AA

Even if Shelia dumps all of her SPG points into AAdvantage miles, she’ll still be 5,000 short. The good news is, it’s possible to place bookings on hold for up to 7 days and it only takes up to 3 days (and normally one) for miles purchased from AA to post to an AAdvantage account.

AA is currently running a promotion on purchasing points. If Shelia needed only 5,000 more miles, she’d receive an extra 1,000 as part of the promotion for a cost of $147.50.

However, if she decided to transfer only 20,000 SPG points into 25,000 AAdvantage miles and needed 10,000 more, than purchasing 9,000 miles and receiving a bonus of 1,000 more would get the job done for $247.50.

If she’d rather hold onto all of the SPG points, one final option would be to purchase at least 35,000 miles to bring her account up to the necessary level. A purchase of 30,000 miles comes with 8,000 more as a bonus – enough to cover the gap – with a cost of $825. Though steep, this would still be less than two cash tickets following the same itinerary, which would be necessary since Shelia doesn’t have quite enough miles for even five people as it stands.

Our recommendation would be to either use all the SPG points and purchase 5,000 miles or use 20,000 of them and purchase 9,000 miles. The right decision rests purely on the likelihood of Shelia using a few thousand SPG points in the future, a prospect she’d be able to best judge. We’ll assume the former in favor of keeping the trip cost as low as possible.

Intra-Island Travel

Happily, Shelia’s family would arrive in Honolulu, allowing them to see Pearl Harbor just a half hour from the city. It might be a long day after the red-eye flight, but this saves some maneuvering between islands later on.

Happily, availability for award flights from the island of Oahu, where Honolulu and Pearl Harbor are located, to the island of Maui, which is Shelia’s desired destination, is exceptional, even with six passengers. 15 separate flights are possible on June 1st, the day Shelia would arrive for the day, with similar availability on June 2nd should she prefer to spend a night in Honolulu before moving on.

If she’d prefer to head to Maui right away, there are 8 flights that leave after 5PM but before 10PM, providing plenty of flexibility to spend a full day exploring before heading on.

These flights are 5,000 miles each way. These should only need to be booked in one direction, as any award flights home from Hawaii using United miles are the same mileage cost regardless of which island you’re traveling from. So, deduct a total of 30,000 United miles from our inventory as we head into the home stretch.

Flying Home

At first, we attempted to find availability from Maui on back to Charlotte. For six passengers, availability was terrible:

What was really disappointing is that availability remained terrible all the way down to just one award passenger. Flying United back from Hawaii just wasn’t going to work, it seemed.

We’re not done yet, though. As it seems to do so often, Ultimate Rewards comes to the rescue when we least expected it.

As we’ve often explained, British Airways Avios can be incredibly useful for certain flights since the program is distance-based in nature. Flights that come in just under certain lengths – like Boston to Dublin or Miami to Grand Cayman – can offer exceptional values. One of these is Maui to San Jose, California on partner Alaska Airlines.

While no availability exists for Sunday, June 8th, which would be exactly 7 days after Shelia and family arrive, that very flight is available for all six passengers on Monday, June 9th for 12,500 Avios each.

Ultimate Rewards points transfer 1:1 to Avios, so Shelia can use 75,000 of her Ultimate Rewards points to cover all six of these flights.

Eagle-eyed readers will notice the above screenshot comes from AA.com, not BA.com. That’s because BA’s award search tool doesn’t allow Alaska Airlines flights to be booked online. You have to call British Airways Executive Club at 1-800-AIRWAYS in order to book any Alaska Air awards.

Because of the late arrival on Monday, it would be necessary to spend the night in San Jose – perhaps at a Hyatt property using Ultimate Rewards points – before continuing on Tuesday. A number of options exist for the flight home, with more availability from San Jose to Maui for the rest of the journey. The best points value among these for six travelers would be on Southwest, changing planes once again in Las Vegas on the way back for 10,800 Rapid Rewards miles each.

All Things Through Points

Consider what’s been accomplished on this return flight: 10,800 Rapid Rewards plus 12,500 Avios equals 23,300 Ultimate Rewards points per passenger, given that’s our source of mileage for both programs.

That’s only 800 more miles per person than it took for the incredibly lucky American award to Hawaii despite the additional challenges faced on the trip back. Even if United did have Saver Economy availability – which they didn’t – the rate would have been 20,000 miles per passenger, still in the same ballpark. So, even though the return had to be broken down into two awards, it came with hardly any penalty thanks to the very effective use of Avios.

Even more importantly, despite the complexities, this itinerary is able to keep all six people together for four different award bookings!

This isn’t meant to be self-congratulatory (okay, maybe a little…), but rather to point out how neat using miles can be – and how much they can save! – with a pragmatic approach and a bit of creativity!

Hopefully Shelia’s schedule can accommodate a couple extra days’ travel time, as it’s definitely worth it given the exceptional savings during a peak travel season.

A Word on Hotels

After booking these flights, Shelia would have the following points balances remaining:

• 0 American AAdvantage Miles
• 70,000 United MileagePlus Miles
• 5,000 Ultimate Rewards Points
• 2 Free Nights at Any Hyatt
• 2 Free Weekend Nights with Hilton
• 0 Starwood Preferred Group Points
• 45,000 Priority Club Points

As such, much of her time in Hawaii will need to be covered through another mechanism, be it additional free nights earned by signing up for the Hyatt Visa – Shelia’s husband has one, but she doesn’t yet – or a card like Arrival that offers $460+ in travel credit toward any travel expenses, allowing Shelia to find and take advantage of the best bargain cash rates available during their stay.

We’ve covered Hawaii award hotel possibilities in the past, so perhaps Shelia can find some inspiration there, too!

Wrapping Up

Trying to find the cash cost of the exact routings used for the award flight wouldn’t be fair, given the extra segment needed on the way home, so instead, we’ll look at the cost of flights from Charlotte to Honolulu, Honolulu to Maui and Maui to Charlotte in our comparison.

We’ll also not include the hundreds of additional dollars Shelia stands to save using her award night certificates, since we didn’t dive into what hotels would be best. However, beautiful properties for both Hyatt and Hilton are located on both Oahu and Maui, and don’t come cheaply, so you can add a bit more onto the total savings line if you’d like to factor them in!

I honestly didn’t expect to find any working option for this trip that kept all six passengers together. To find a way to do it in fairly peak season proves, in my mind, that almost anything is possible with points and miles with a bit of luck and creativity.

We hope Shelia will be able to take advantage of this routing, as such an award for so many people doesn’t come around every day!

Happy travels!