My goal is to go to Hawaii next year. We have 100,000 UR points. I should have 120,000 SW miles and CP within 3 months. We have to use both new SW cards the next 3 months so we won't earn any UR. We maxed out Freedom 5% the last 2 quarters. DH is 2/24 and I'm 3/24. We have 3 SW cards, CSP, and Freedom. We spend a lot on groceries and gas (at least $1000/month), which card should we go for next? And by next, I mean in 3 months. This is so exciting, trying to get to Hawaii for super cheap.
You and your husband can do 2-Player mode, so you each can apply for the same cards if there's a good bonus, or strategically decide one of you will apply for one card and the other apply for something else or not (for example, to stay under 5/24).
In the short term, while you and your husband are still under 5/24, I'd suggest focusing on Chase cards that will earn you the most UR points and give you the best redemption value because you can use those points for flights or a stay at Aulani (or any number of other accommodations in Hawaii).
You can go for another CSP, if you don't have two already, which will give you another 50,000 UR points.
The next obvious choice is the Chase Sapphire Reserve (CSR), which could earn you 50,000 UR points after $4,000 spend/3 months (or double that if both of you apply), and stretches the value of all your UR points by giving you 50% more value in travel redemption through the UR portal.
When you’ve earned the bonuses from the Sapphire cards, you can product change them to more Freedoms, since you’ve been maxing out the categories; or to a Freedom Unlimited, which you can use for general, non-bonus category spend to earn 1.5x UR points for everything else – which then stretches to 2.25x UR points when you transfer the points and redeem them through a CSR. Obviously, one of you should keep the CSR. If you’re product changing within one year, you may first need to change to a no-fee Sapphire, then to the CF/CFU.
Longer term, you may want to look at an airline card that will earn you miles to fly to Hawaii. I don’t know where you’re based, so I can’t give you specific suggestions about what airline services your local airport with routes to Hawaii. But Southwest doesn’t fly to Hawaii, so you’ll need something else.