I'll think about it and try to come back with some ideas. Our family tries to make it back to Hawaii every year, but our situation is a little different because my wife has family in Honolulu, who we can stay with, so we don't usually book lodging aside from a splurge for a few nights at Aulani.
Some initial thoughts:
- Southwest doesn't fly to Hawaii (yet; but there have been rumors for years that SW will start up Hawaii routes "soon")
- Hawaiian Airlines probably offers the most convenient, direct service between Guam and HNL.
- From the west coast, Hawaiian also services SFO, SJC, OAK, LAX, SMF, SAN, PDX, SEA (and LAS, and PHX). Hawaiian also flies to and from JFK.
- If you go for the Hawaiian MC, apply for the 50k HawaiianMiles offer by going to the Hawaiian Airlines website and starting a "dummy booking." Before you pay for any reservation, there should be a banner ad that pops up with the higher offer. The public offer is only 35k.
- 50k HawaiianMiles is usually enough for one roundtrip award between Hawaii <> North America (the "mainland" as locals say in Hawaii). See Hawaiian Airlines awards table:
http://hawaiianair.custhelp.com/app/answers/detail/a_id/2218/~/book-award-flights.
- Flight (and award) availability for Hawaiian opens up 330 days out, so have your dates and points ready to book by then -- especially if you're traveling during a busy time (basically spring break, summers, the holidays, and whenever the kids are out of or traveling for school).
- For example, I once had to book a last minute flight from SFO<>HNL in October and award availability was still available for 42,500 miles roundtrip and about $12 in fees/taxes. Another time, around 300 days out, I couldn't for the life of me find any award availability between mid-December and the second week of January.
- The Hawaiian MC offers a one-time 50% off companion discount for travel between Hawaii <> North America, but I believe the terms require the primary passenger's ticket to be a cash fare. Free first checked bag too.
- Another benefit of the Hawaiian MC is that anyone can transfer their HawaiianMiles to the primary cardholder free and instantaneously, so the cardholder can pool everyone's miles together.
- You can book Hawaiian Airlines award travel for others, but I believe the cardholder needs to be on the reservation to use benefits like the companion discount and free checked bag.
- You don't earn miles on award, discount, or codeshare flights, but if you pay cash on any Hawaiian ticket, it makes sense to get a HawaiianMiles account for that traveler so he/she can earn miles towards your next vacation.
- If you have the Amex Premier Rewards Gold card, it offers an annual $100 airline fee credit that works when buying a $100 Hawaiian Airlines gift certificate. The Amex Platinum has a $200 airline fee credit that works the same way. But buy gift certificates in at most $100 increments, or it won't credit. You can use up to 4 gift certificates per transaction.
- Amex usually runs a 25% transfer bonus promotion every year with Hawaiian Airlines: 1000 MR > 1250 HawaiianMiles. Note: there may be better uses for your MR points, and Amex charges fees/taxes for transferring miles to partner programs.
- I've been monitoring cash fares for flights from SFO to HNL during the holidays since early this year, and Alaska/Virgin America often dropped to the lowest fare available so definitely look into Alaska as a possibility.
- Also check out Singapore Airlines' KrisFlyer program, which you can use to book on Alaska:
http://www.singaporeair.com/saar5/pdf/ppsclub_krisflyer/charts/AlaskaAirlines_AwdChart.pdf. It's as low as 12k miles to fly from the west coast (Zone 1) to Hawaii (Zone 5). You can transfer UR, MR, SPG, and TYP to KrisFlyer.
ETA: Travel hacking to Hawaii is such a popular topic, I've seen countless articles on the points and miles blogs about it. There's a wealth of information out there!