I would try to see if they would review your file with your score on record despite you being registered for a future test, or if they would place your file on hold automatically. Applying in December with a median LSAT and your GPA wouldn't be bad, but you're not guaranteed a higher score. The predictor gives you a good chance at Chicago with your current stats if you apply now, and the odds go down slightly if you apply in December with the same 169 score. If you apply in December with their median 171 your odds aren't much higher than they would be now. Of course, the predictor is not perfect and you shouldn't base your decision off of it. If it were me and they would review the file as is despite the pending future test I would apply now.
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I would try to see if they would review your file with your score on record despite you being registered for a future test, or if they would place your file on hold automatically. Applying in December with a median LSAT and your GPA wouldn't be bad, but you're not guaranteed a higher score. The predictor gives you a good chance at Chicago with your current stats if you apply now, and the odds go down slightly if you apply in December with the same 169 score. If you apply in December with their median 171 your odds aren't much higher than they would be now. Of course, the predictor is not perfect and you shouldn't base your decision off of it. If it were me and they would review the file as is despite the pending future test I would apply now.
Go for it!!