Even if your last date here involved an empty bar and an old woman sobbing in the front window, there’s no denying that the Charleston is a primo first-date spot. When there are more people (so not on a Sunday at 4pm), the neighborhood bar is narrow, dimly lit, cozy and low-key. It’s sexy if you need it to be, divey if you don’t. Great beers on tap. Wine too. Oh, and cash only. No crying allowed.
2076 N. Hoyne, 773.489.4757, charlestonbarchicago.com
Best of Chicago 2016