Dr Jabadski

At that level of annual spend and travel, suggest you consider multiple cards as multiple SUBs will generate MUCH greater rewards. With 2 (or 3) players, between Chase and AmEx (MR cards which can redeem for UA flights), there are many options.

If aggressive credit card applications is acceptable and possible, suggest annually alternating UA Club card and another UA card between you and your wife (and maybe your daughter). The Club card high annual fee makes it less desirable to keep open after 13 months, the high SUB “pays” for the first year annual fee and has several better perks when spending and flying on UA.

After 1 year of Club card, suggest another UA card (Biz Club, Explorer). If amenable to a Biz application, same logic applies to the Biz Club card. If not, then Explorer.

Once it’s been 25 months from last Club card SUB (presuming it was closed at 13 months), reapply for that card. Wash, rinse, repeat.

FWIW, as a solo player, I’ve been successful in churning UA Club card and UA Biz Club card every 13-15 months for several years so that I’ve never paid a second AF and always have one or the other open (to take advantage of benefits). FWIW, I’ve also been successful in doing a similar churn with Hyatt cards (personal and biz) so I rarely pay a second year annual fee (personal card only, gets a FNA and depending on timing gets some “gratuitous” elite qualifying nights) but can still get a SUB almost once per year.

There are multiple Hilton cards with significant SUBs and benefits, even for infrequent Hilton guests, and there are many Hilton options near ORD and Chicago. (The Air BNB debate is off topic for this thread, suffice it to write I’ve read more than enough horror stories.)