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LSAT: 170 and GPA: 3.54. Masters degree. Three years working for federal government in very legal-oriented role.

What are my chances at UChicago? Berkeley? Pennsylvania?

Would it help to take some local masters classes?

Does it matter that my work evaluation is consistently 1.9/2.0 (well above the median)?

Given that 170 was unusually low for me and I'm applying next year anyway, should I retake the LSAT?

First, apply to Northwestern given your work experience.

And you should have a shot at all those schools except Chicago. If you want to increase your chances and you are confident, a retake would be nice, but it isn't absolutely necessary. You should probably get at least one T14 to bite.