While we had planned to fly to Hawaii in August of 2018, we were unable to go on that trip and had canceled the flights we had bought on miles. We paid the fee when we canceled so we wouldn’t lose the 180,000 points we had transferred to buy those tickets originally so we had a hefty stash of points on United to use.

Searching for Availability

I searched for paid fares for the times we were looking to go as a baseline to see if using miles was a good value. Flights were close to $1,000 per person so if we could find availability at the saver rate of 45,000 points per person round trip on United would provide an excellent return.

In addition, using miles on United would let us use what is known as the excursionist perk. In short, when you travel to a different “zone” (Hawaii is a different zone than the continental US), you can get a free segment within that zone for no extra points. This meant we could fly to the Big Island on one leg, get a free leg from the Big Island to Maui for no extra points, and our return leg from Maui to Boston.

While inter island flights aren’t terribly expensive, it can definitely be a money saver. It was like getting $300 in tickets for 0 points, which is a good deal in my book! There are lots of interesting and much more complex uses of this perk and there are blogs with countless examples of you to maximize it’s value. For us, we just wanted to use the simple case and do an island hop. It made using United points more valuable to us for this specific trip.

Finding Itineraries

Searching for flight availability to Hawaii In the summer with points can be challenging. With some programs points are cash equivalent which makes it simple, but gives you a fixed value for the points which is usually on the low side. United has an award chart (though they are moving away from that in the fall of 2019) with the lowest saver level tickets from the continental us to Hawaii at 45,000 points per person round trip. Hawaii is a popular destination and awards at that level can be hard to find, especially if you need 4 of them and with at least one connection like we would from the east coast.

One of the perks of the United MileagePlus Explorer credit card I have is that it gives me access to more saver level awards than people without status with the airline. This makes is somewhat easier to find availability, but many days we looked at there wasn’t anything at that level. There were was availability at 90,000 miles round trip but at that price it was not worthwhile to use the points.

Eventually I was able to find saver availability for a two week span that included the 4th of July. We’d be flying from Boston to Kona on the Big Island with stops in Denver and Maui. While a two stop itinerary was less than ideal, we had reasonable layovers and could get good seats on a preferred type of plane on the longest leg from Denver to Maui. The Maui to Kona leg would be a short 20 minute flight on partner airline Hawaiian.

After four days on the big island we’d take a mid afternoon flight back to Maui on Hawaiian. After 10 days on Maui we’d be taking an early evening flight back to Boston via Chicago. This gives us a longer red-eye flight On a larger Boeing 777 on which we could get more sleep, at least in theory. After a short layover in Chicago we’d be back in Boston mid-morning, hopefully rested enough to get through a day of work.

All this cost us the 180,000 points we had from our canceled trip the previous year as well as $44.80 in taxes and fees, booked directly on the United website. I put the taxes and fees on my MileagePlus Explorer card as that would allow us one free checked bag per person as one of the perks of the card. In order to get the perk the card holder must be on the itinerary and use the card to pay for the itinerary. This works even if the itinerary is just the taxes and fees on an award ticket.

With the dates set we could look for places to stay.