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Congrats on the good GRE scores -- it's nice to have those out of the way. If you aren't in touch with prof. #1 at this point, then #5 is a better choice. Did #5 know at the time you worked for him that you wanted to go on to a PhD? I'd simply ask him if he thinks he can write you a good letter for econ programs -- there's a lot of overlap between econ and policy at Chicago, but different students follow different paths within the program, so just make sure that he's in the world of economics and feels that he can write you a useful letter.
(And I think it's perfectly ok to discuss with your professors who should write your letters. I had completely frank conversations with my professors about who my choices were -- and some told me to choose someone else over them, either because of connections/seniority, or because of the expected content of the letter. Knowing who my other letter writers were also helped each professor plan what to say, to make sure all bases were covered.)
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