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"I would recommend putting your spend on Amex PRG or BRG, it gives 3x on travel."
I think the Amex Gold cards might make sense for the OP if he can get a sign-up bonus better than the 25K point "standard" bonus. We don't know how much the OP charges annually on "travel," but by his estimate, he will be spending less than $4,000 on the anticipated 11 roundtrips to CHI. If the bulk of his points/miles is going to come from sign-up bonuses rather than spend, I'd probably go with the Chase/BA Avios first. (But the OP could certainly get an Amex Gold card in addition, as long as he thinks he can meet the spend requirements on both cards.)