Questions and Answers

Hello,

I have a question about the best card combination to capitalize on about 2.5 years of upcoming travel I have.

I am a Boston native who is planning on attending graduate school in Chicago beginning Fall 2018. I will be attending a weekend program and traveling ~25 weekends each year. Currently, I have the CSR, which is great. I use it for business travel and really love the perks/points. However, I feel like I wouldn’t be maximizing my spend if I stuck with purely the CSR next year. My plan is:

– Fly Southwest in/out of Chicago from Boston each weekend (Would Southwest card(s) be appropriate here to earn Companion Pass)?
– Spend one or two nights each weekend in Chicago (Considering AMEX SPG card here to put this spend on… good idea)?
– Retain CSR for dining and other non-Southwest travel expenses.

I’d love to know if this generally makes sense or if I’ll be spreading the spend too thing to earn enough via any one card.

Thank you!

If you’re committed to flying only Southwest, then their card is a good option. Do the math and see how close it might get you to the companion pass.

Another option would be to fly United or American, as ORD is a hub for both. 25 weekends equates to 50 flights. Both MileagePlus and AAdvantage require 60 segments to reach PremierGold or Platinum. If you fly with a connection a few times, you could easily attain that status.

Might be good to stick with just the CSR, fly United and stay at Hyatt hotels, given that travel earns 3x and Chase UR points transfer to United and Hyatt.

I’d second David’s suggestion to look at American or United. If you are traveling every weekend for your program, I don’t know if you’d see any value in Southwest Companion Pass. Would you even have time to take extra trips with a +1?

On the flip side, with American/United you might have a decent chance at upgrades once you earn status… especially if you are flying on weekends and non-traditional “work” days