Think your best bet is to set a priority list, balancing location, academic/community, sub specialty options, etc. If location is really the far and away number 1, there are several programs in Chicago area, apply to all of them, and be aggressive in sharing your love for them when the time comes. That being said, it's hard to play the Match game on location alone, especially with OB becoming more competitive, so don't apply to only Chicago. Make a regional list of what's an acceptable driving distance and be open to the possibility that you'll need to be flexible. OB is a busy specialty and it's likely your free time will be tough to coordinate with your SO, regardless of your location.
226 is certainly a match-able score with all the other credentials, and it will help to kill Step2, but you just can't be picky with programs if location is your #1 criteria. Picking 40-60 programs to apply to will mean moving further out of your radius; I know people who applied to less last year and did fine, but most were TX or CA applicants wanting to stay local.
And OB doesn't require aways, though they're more popular. If you're going to do one, do it in Chicago and work your tail off. Even if you don't end up there, a good letter from someone with a local reputation will carry weight.
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