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Ali Trachta of Chicagoist lists a few restaurants and bars that regularly offer free food. Among her findings: N9ne, Kitsch’n, Red Kiva, and Finn McCool's all offer some sort of free happy hour snacks; Cleo's has a similar deal, but closer to midnight, and Enoteca Piattini has a buy-one-get-one-free deal for entrees on Sunday nights. Feel free to expand the list in our comments. If it gets long enough we'll aggregate them in another post.