I have only opened one card in the last 24 months Chase Sapphire. And trying to recall but I believe it was between 12-24 months
As we have been doing a remodel, we have been buying supplies with the card and then paying it off.
We dont usually carry a balance, we try to pay it off every month
We fly out of PDX ( Portland)
I have a SW card, but am considering closing it as I no longer use it, my husband does not like to fly southwest We booked Florida airfare with rewards and I've booked a flight to LA with my daughter with rewards, but otherwise my husband doesn't care to travel with them
Our preference is Alaska or Delta, I have had an alaska card and keep it for the companion fare, but have regularly found that their prices are higher and sometimes the companion fare doesn't save us that much.
Our travel party is either 2 or 3.
Our favorite destination is WDW...but Maui has been on our list for years and years.
We are trying to not take our daughter out of school like we did when she was younger, so we are looking to travel to Maui over Thanksgiving break or Christmas....but would possibly consider fall. Sept/oct
We usually stay with our timeshare, or rent via VRBO or such
i do have points with marriott and holiday inn, not alot but some
We just traveled to Hawaii (Kauai and Oahu for Aulani) from December 27- January 6. I was able to transfer 15600 URs to British Airways and book one way flights on American for December 27th. It looks like I booked on September 5th. We flew Southwest on the way home. Hawaii during Christmas break is magical, but expect it to be busy! And book rental cars early and keep checking for them to drop. Also I would start looking for hotels now. We love both Maui and Kauai!
@blakefamily - I'll circle back to this when I have a little more time.
Some quick thoughts. We travel to Oahu every Christmas/New Year's. I have to be really on top of fare and award releases to get the best deals, or else I'm scanning Google Flights, Hopper, Expert Flyer, etc. for deals the rest of the year until I find something I'm ok with booking. Most airlines release their schedules and awards ~11 months out. That means flights over Thanksgiving week are already on sale or available for redemption. Flights for next Christmas and the New Year will be released in about 2-3 weeks. I always try to have all my points or miles in place about a year out and ready to book. Flights during the holidays are always challenging to book with the least amount of damage to our points and miles banks. That's not to say you can't find good deals after the initial release, or that you can't use credit card signup bonuses to offset the cost of airfare. Cash fares go up and down, and points that can be used like cash like Chase Ultimate Rewards (UR) points can be used to pay for those fares. An airlines saver awards and flash sales are harder to predict.
(I checked Hawaiian Airlines' award prices for PDX-OGG for the weekend before Thanksgiving, and it's already at 85k HawaiianMiles per person, one-way departing on Saturday. Sunday and Monday departures are 52.5k HawaiianMiles. Midweek departures are 26,250 HawaiianMiles. For comparison, the current signup bonus on the HawaiianMiles credit card is only 60k HawaiianMiles. Hawaiian has a kind of dynamic award pricing and those award prices will likely keep going up.)
I'll throw out another suggestion to consider: Spring Break, if that works for your schedule. I find ticket prices from the West Coast to Hawaii to be a lot less expensive immediately after the holidays in January through about early May, especially for midweek travel; but prices do creep up around late March and early April because of spring break. It's a little less of a rush than the holidays, because everyone's spring break schedules are different so the demand is more spread out. Midweek travel during these months this year is running as low as about $300 round trip. Our family is actually flying from SFO to OGG (Kahului, Maui) over spring break, and fares are down to $229/per person each way on weekend itineraries. We have a DD6 that we don't like to pull out of school for vacations either. After checking the miles or points it would take to book award seats on United, Hawaiian, and Southwest directly, we decided the Chase UR travel portal allowed us to use the least amount of our points. Using Chase Ultimate Rewards (UR) points on our Chase Sapphire Reserve (CSR, with a 1.5x travel redemption multiplier), a $229 flight is about ~15,267 UR. With a Chase Sapphire Preferred (CSP) or Chase Ink Preferred (CIP)(1.25x travel redemption multiplier), that $229 flight runs about 18,320 UR.
You're flying out of PDX, which should have a lot of options to get to OGG. I haven’t done searches for Delta, AA, United, Hawaiian, Alaska, Southwest (via PDX-California-OGG), but you’ve got options. I think
@WardFam's method is worth looking into, by transferring Chase UR points to British Airways Avios, then using that to book partner saver award availability on American Airlines. But first, you'd need Chase UR points.
Since you opened a "Chase Sapphire" card in the past 24 months, you're locked out of a signup bonus for all other Sapphire card products for 48 months. But have you considered opening a business card? It doesn't take much, and you may already have a "business" without even realizing it. If you sell things online, do freelance work, tutor, babysit, pet sitting or walking, bake and sell cookies, you can qualify for a business card. Chase has several business cards with high signup bonuses, including the Chase Ink Preferred with 80k UR (CIP), Chase Ink Cash with 50k UR (CIC), and Chase Ink Unlimited with 50k UR (CIU). But for good reason, you should be looking at the CIP.
I know a lot of people here have experience travel hacking Hawaii and are eager to help. Please don’t rush into signing up for anything just yet, because you have options to explore and we don’t want you to make any missteps once you settle into a plan and develop a strategy.