@disneymagicgirl, it's really sweet of you to want to plan a Hawaii vacation for your husband's 40th, but I'm sure he wouldn't want you to stress as much as you are to make it happen. This is where I kind of defer to
@calypso726's guideline of planning vacations two years out. You've got a lot of points in different programs, but I think there are a few changes in the coming months that really favors putting off Hawaii until next year. As
@Albort mentioned, with Marriott finalizing its merger with SPG, you'll probably be able to book the Westin Ka'anapali as part of Marriott's Flight and Hotel package and get a better deal. And with Southwest poised to start flying to Hawaii late this year or early-2019, it'll give you a lot more flight options.
The difficulty is you're in the middle of the country without easy access to a lot of the direct routes to Hawaii, and on top of that you've got to find award seats for 6 people. Three of the airlines that have been discussed --
Alaska,
Southwest, and
Hawaiian -- have some form of companion discount.
- Southwest's Companion Pass, you know, and is probably the most generous of them all. Unfortunately, Southwest still has yet to announce the details of their Hawaii plans, much less make tickets available for sale.
- Alaska has the Companion Fare, which is offered to their Alaska Airlines Visa consumer and business cards. (The Alaska cards are issued by Bank of America, and DoC confirms they do not report business cards to personal credit reports. However, I don't know how difficult it is to get a "business" card from BofA.) Alaska's Companion Fare offers an annual roundtrip coach companion fare on Alaska for just $99 plus taxes and fees starting from ~$22, when traveling with a paying passenger on the same itinerary, booked at the same time at alaskaair.com. I believe Alaska has a limited time signup bonus where the $99 base fare is waived for the first year.
- Hawaiian has a Companion Discount, which is offered to their Hawaiian Airlines World Elite and Business Mastercard cardholders. (The Hawaiian cards are issued by Barclays, and again I don't know how hard it is to get approved for a "business" card, and there are conflicting reports whether Barclays reports business cards to personal credit reports.) The standard signup bonus for the personal card is 35,000 HawaiianMiles (which is usually enough for one roundtrip from the Mainland to Hawaii, but award availability becomes almost impossible from the week before Christmas until about a week after New Year), but you can do a dummy booking on hawaiianairlines.com and get targeted for a 50,000 HawaiianMiles signup offer (I was able to pull this up two weeks ago). (DoC reported recently that Hawaiian is handing out paper applications with a 60,000 HawaiianMiles offer in flight.) Back to the Companion Discount, new cardholders get a one-time 50% off companion discount for roundtrip coach travel on Hawaiian between Hawaii and the Mainland, and a $100 discount off a roundtrip coach companion ticket upon each account anniversary thereafter. Hawaiian's Companion Discount is only good for companions traveling with the cardholder on a paid ticket, on the same reservation, book through the the cardholder's HawaiianMiles account and using his/her Hawaiian Mastercard.
So if you can't get all 6 travelers on award seats and you have to pay out of pocket for some of the tickets, the above companion discounts could help cut down on your cash cost.
Southwest: Companion flies almost free (+taxes and fees).
Alaska: Companion flies for $99 +taxes and fees (possibly free + taxes and fees for the first year).
Hawaiian: Companion flies for 50% off for the first year, gets a $100 discount after each account anniversary (with even "cheap" roundtrip fares from the West Coast to Hawaii costing ~$400 in the low season/midweek, 50% off still leaves you paying at least $200 for your companion.)