Best credit card combo if I can book everything on my personal card? Fly out of MDW and typically stay at Marriott.

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If u want to go for companion pass then you should book your SW flights on a SW credit card. I would apply for the SW Performance business l, which is the only SW card that gets 3x on SW flights. (All others are 2x)

For the hotel it largely depends on what kind of rewards you want. You could get the CSR for 3x (and can transfer to SW at 1:1, thus getting 3x SW miles on hotels). Also gets 3x on dining. Or the high end Marriott chase/Amex cards that get 6x Marriott points. (But they are worth 1/2 as much as chase points)

All in all I would get SW Business + CSR

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As a side note, if you are able to hit CP consistently simply based on your flight miles earned (not credit card miles) then I would just throw everything on the CSR.

I’d get both CSR and Amex plat, then just add on the Bonvoy card for points and anniversary nights. If you have a partner, ask that person to get it too. Then you guys can have a weekend getaway for essentially free every year

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Ooof why MDW?

TSA PreCheck lines at ORD have consistently been under 5 minutes, with my sample size being 200+ flights out over the past 5 years. How could MDW be any shorter than that?

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I have a personal SWA, business SWA (earn and churn every 49 months), CSR. That gets me where I need to go 9/10

And if you play the churn right, you can pretty much have an eternal companion pass.

AMEX Plat will get you the best return on flights but unless you’re booking through their portal it’s only 1X on hotels. I’d get the Plat and one of the Marriott cards. The free night essentially pays the annual fee.

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