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@SouthFayetteFan to join the dischurners reddit group and read this post
Basically, if you open 2 SW cards (both biz) then you can hit 125,000 pts and earn a companion pass. Thus would let one of your travel party fly free. That plus the 125,000 points should cover all of your flights or close to it. Whats your preferred hotel chain? Marriot, Hilton, Hyatt, IHG - all have cards you can sign up for to obtain points. Because Hilton, IHG, and Marriot have 4th or 5th night free you can extend those points further on longer bookings. Hyatt has low point cost per night at some hotels but a smallerfootprint. With 5 you may find Hilton your best bet since you could use points at Embassy Suites or Doubletree Suites or Homewood Suites to get a larger room.
Eta- a quick note, we don’t recommend more than 1 Chase issued card every 3 months (but you and your husband are considered separate so you could stagger there- DONT make each other AUs). Also if you are unsure of your preferred flights or hotels, or don’t want a tie in to one chain, you could consider a UR (ultimate rewards) card that earns Chase points good for transfer to certain partners or redeemed at up to 1.5x through their portal (expedia basically). The recommended card there would be a Chase Ink Preffered if you can do a biz card. ANY biz (selling ebay/fb/babysitting ect) can count.