Plan Hawaiian Vacations on Miles: Strategic Airline Ticket Decisions

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Plan a Hawaiian Vacation Using Miles and Points: Part 1 (Overview)

Strategic Airline Ticket Decisions (this post)

In Part 1 of this mini-series, I outlined what I would be covering in subsequent posts on getting your family to Hawaii on miles and points. If you missed that post, I recommend going back and checking out some of the tips and parameters shared there to give a baseline for what is to come. The next couple posts are dedicated to using miles to fly to Hawaii, primarily from the US, but many of the tips will apply to those in nearby Canada, Caribbean, etc. Before I get into a list of what airlines can be used at which mileage prices, I want to cover some decisions that will impact which type of miles and tickets are the best for you.

Decide on Premium Cabins vs Coach:

For a domestic trip, Hawaii is pretty far away. From the East Coast it is over a ten hour flight. That is several hours longer than the East Coast to Western Europe. Even from the West Coast, the flight rings in at close to six hours. So, it is totally reasonable for people to strongly consider making the trip in a premium cabin given relatively long flight time. But in this case, not all premium cabins are created equally. Many carriers operate flights to Hawaii where the first/business class cabin is nothing better than what you would find on any other (shorter) domestic route. The seats don’t lie flat and the meals are just slightly better than edible. Granted, that is still better than what you will get in economy, but it may or may not be worth the increased number of miles for the only moderately improved trip.

Below is a shot from my recent United flight from San Francisco to Maui. The seats didn’t lie flat and the IFE was not exactly impressive. My seat was better than coach, but not something I would spend a crazy amount of miles on.

I recommend doing research on the carriers and routes that interest you to see what type of configuration they use to go to Hawaii. Be aware that it may also vary seasonally, so don’t base your info off of one search if this really matters to you. I’m by no means a premium cabin expert, but I will say that the key feature of a good premium cabin on this route is a seat that you can sleep in. I would strongly prefer a lie-flat seat, but even an angled lie-flat seat is better than the regular domestic first class seats. Many of the flights coming back are overnight flights, and being able to really sleep on that flights makes a huge difference over coming back home totally exhausted. Of course, being able to get some rest going doesn’t hurt either.

Some routes that do provide lie-flat seats on United are from hubs like Houston, Newark, Denver, and San Francisco to Honolulu (typically in first on a 777-200 three-cabin plane and in business on a 767-400ER two-cabin plane). On American, look for the 767-300 planes out of hubs like Dallas and Chicago (when this route is operating).

Of course a premium cabin will cost more miles (often double) than coach. If you want first class in a three-cabin plane it will cost a little more than twice the cost of coach. If you only have the miles to fly in business or first in one direction, I would absolutely recommend it be on the way home since that will be a night flight. I care about quantity of sleep more than the quantity of Mai Tais or in-flight movies, but if your priorities are different than perhaps you would enjoy first class on the outbound flight more.

Consider the “free” or cheap one-way reward flight:

A few different airlines offer a “free” or cheap one-way ticket to Hawaii if tacked on to a different award reservation. The two simplest I am aware of are via American Airlines and United. Here is an example…Say I want to go from Houston to Istanbul and back on an award ticket. If I wanted to just cut to the chase I could book Houston – Istanbul – Houston in business class for 100,000 United miles. However, on that award ticket I could instead go Houston – Istanbul – Houston – Honolulu for just 7,500 more miles due to the award chart. You can put a long gap in between returning to Houston and heading to Honolulu by using a long stopover. In this case, I would effectively be getting a 40,000 mile one-way award in business for just 7,500 by tacking it on to my award to Europe. In economy it is 2,500 extra miles. Of course, I still have to get back from Hawaii. I could just book a one-way award home via the standard route, or tack the return onto a different big award ticket in much the same way I did the first time to save a bunch of miles, just on the front-end instead of the back-end.

Alternatively, if I had no plans to head to a galaxy far-far away on an award ticket, I could still eek out extra value from a Hawaii award ticket on United by adding a “free” one-way. Again with Houston as the example, I could fly Houston – Honolulu – Houston (stop for however long…months even) – New York for the same price as if I only flew from Houston to Hawaii and back. This comes from maximizing stopovers, open jaws, and the generosity of the United Gods.

If you would rather fly on American miles then you can actually stack a free one-way to Hawaii on the front and back end of a “big” award ticket to a place like Europe. For example, I could fly Maui – Dallas (stop for a while) Dallas – Paris – Dallas (stop for a while) – Maui all for as low as 40,000 miles in economy during the European off-peak season of Oct. 15 – May 15. The trick with this is it really only works from a “Gateway City”, meaning the last city you are in before leaving the US on your international award ticket. Those cities can include American hubs like New York, Los Angeles, Dallas, Miami, and many others depending on where you are headed outside the US. Heck even though it is far from a OneWorld strong hold, my own Houston could be a Gateway city that would theoretically work for these purposes if I was flying on a British Airways flight using American miles directly to London out of Houston (though the BA flight would hit me with a ton of fees).

Booking using free or reduced cost one-ways to Hawaii is very rewarding, but it does require some research and planning far beyond what I offer here in this post. You need the capacity to essentially be booking two trips at the same time. You are also limited completing all travel on that award within one year from when you book the ticket. So, this doesn’t work if you want to put years between your trips. Even though this is just very introductory info on the topic, I wanted to mention this here as it is very relevant to planning trips to Hawaii. I will cover the best traditional options of using miles and points to get to Hawaii, but those deals will typically pale in comparison to being able to just tack the trip on “for free” to another award.

If you want to learn more about this, head to Milevalue as he has the most comprehensive info one the topic in his series on “free” one-way awards.

Once you have decided on which cabin is right for you and whether or not to make use of free or reduced price one-ways to Hawaii, it is time to learn about which type of miles and points are the best deal for getting to Hawaii, and that is what I will cover in the next post in this series.


  1. How’s Hawaiian? Many of us churn the HA BofA card with 35K bonuses. They have a non-stop from NYC which would seem a bargain. Is their F or J any good?

  2. The biggest challenge, in my opinion, will be finding availability of those lie flat or almost flat seats. Even looking out 300 days those seats are far and few between.

  3. I have always been intrigued by this concept. My problem is not being a premium FF on any airline hampers one’s ability to do this…..I think. If there are many months at the stopover city, that means that the 331, or whatever, days can be many months after (or before) the desired departure on the big trip. To me this means that if I want to do this I risk not having availability for the trip I REALLY want to take. Or I could book the trip I really want to take and then pay change fees to add on the “free” leg. Am I figuring this correctly?

  4. Being on the west coast though, doesn’t make much sense to fly, lets say PDX-DFW-HNL, just to get a lie flat seat or something. AS offers non-stops from PDX/SJC/LAX I believe and its a 5 or 6 hour joyride on a 737-800. Granted, not the best way to go, but one of the fastest. I think I rather do HA’s 767 though from PDX.

  5. MommyPoints, if you don’t leave near a gateway city is it worth it? Meaning, if I have to first position myself to a gateway city (Dallas or Chicago) for all the legs of the trip (a potential Europe and Hawaii award ticket) would this not be recommended?


  6. Adding a “free” segment is much more difficult that it sounds. You have to find matching availability for two different trips at the same time. As for buying the other half of the Hawaii flight, a one way ticket costs so much more than half of a r/t ticket that it usually isn’t worth it. So now you have to be able to find availability for 4 one ways at once. All within those 331 days. I’ve gotten FC TA award flights every year for decades, but I’ve only tried and failed to add on the Hawaiian part. Without even thinking about the quality of the cabin. 🙁

  7. -Availability is an issue (as with all rewards), but is not at all impossible if you start looking early and have flexibility.
    -The free segment is often booked at the time you book the “main” award. Yes, it can be tricky and it doesn’t work for everyone, but is worth trying if it sounds interesting to you. I really recommend reading MileValue’s linked series if you are serious about wanting to try this out. I mentioned some stuff here, but he has a ton more written on the subject.
    -Whether positioning is worth it depends on how far you are. In general though positioning is too much work for most families.

  8. I did a Churn about 6 months back just to get FC tickets to Hawaii. Flying out of JFK on Hawaiian and back to EWR. We had no problem with getting seats on United and booked 4 seats (going with friends) for 40k but Hawaiian proved to be way more difficult. I booked the first date it came open and it allowed me only 1 seat at 40k and the other seats at 80k.

  9. Agree with you totally re the business seat option on use of points, namely to use on one way when coming back on the overnight leg of the trip. Additional reason of basic psychology – if going on a family trip to a really beautiful and fun destination, the trip there always seems ‘shorter’ and less arduous – the power of anticipation of a nice stay in paradise just ahead?

  10. @Robert – “As for buying the other half of the Hawaii flight, a one way ticket costs so much more than half of a r/t ticket that it usually isn’t worth it.” International, yes. For almost all domestic markets, this is not accurate.

  11. Interesting timing of this post, since I recently took advantage of this very scenario while planning a family trip for four to Paris during April vacation. After playing around for quite a while, I was able to get AA flights from JFK to Paris and back again, and then tack on the free one-way for the last week of August from JFK to HNL (160k AA miles, mostly thanks to three Citi AA cards — though I had to have a leg from CDG to LHR on BA, which jacked up the fees). For the return one-way from HNL to JFK, I booked the nonstop on HA for Labor Day (120k HA miles, thanks to BofA and BofH HA cards for my wife and I). Now, clearly this is all Economy class, so I’ll see how “clever” I feel about this arrangement after I come back from both trips, but at the moment I’m pretty happy 🙂

  12. How do you recommend flying between Islands in Hawaii. Thinking of using United miles and then they charge 5k miles to island hop which seems okay to me, but does it impact your ability to add on that last leg of the trip for free? [e.g., DEN-LIH-Honolulu-DEN-NYC] Does that work? I have BA miles–could use those to hop islands instead.

    I would love to try to get to Hawaii with my family off peak–in November of this year possibly.

    Thanks in advance for your advice!

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