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Coming from top 15 undergrad, 2 years strong work experience. 167 LSAT in September, 3.4 GPA. Would love to practice in Chicago and thus NU and Michigan are top choices, but will also target some other schools. LSN seems to show people in my position getting a significant number of rejections, but if you increase the score to 168/169, rejections mostly give way to waitlists and acceptances. Wondering if it is worth applying now and then submitting December retake later. Just wouldn't want to get dinged before getting December score back in early January. Worried more about getting in places than scholarships at the moment. Thoughts?

I'd wait to apply until you have a higher score. If December doesn't break your way that would be a lot of wasted app and LSAC fees.