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Have worked for 3 years in urban school through teaching program. Trying to determine whether to retake LSAT and apply Janauary or apply now.

Apply now early decision, but also retake. You probably won't get the full-ride, but it makes your app look infinitely better when you get rolled to RD. I have a friend with similar WE/slightly worse numbers who did this. The retake will pretty much lock you in if you get another point or two on the LSAT.

Thanks for quick response. What would be my chances early at either Michigan or Chicago?

No chance at either. Definitely not Chi. You MIGHT get lucky and sneak in off a WL at Mich, who knows, but extremely unlikely.