Disclaimer: I have only been to the Hopleaf twice, and people who I trust say that they like it and that I should give it a third chance. However...
The Hopleaf has somehow managed to build a reputation as the foremost beer bar in Chicago. It's true that they have many good beers, but when I look at their menu, I see nothing that I can't get cheaper somewhere else in Chicago (Notably the Maproom, Smallbar, and the University of Chicago Pub.) Frankly, I have never seen such a long menu of beers that don't really excite me. Add to that a prevailing air of pretension, bartenders who didn't seem to give a crap that I was there, and the fact that they wouldn't even let me sit down because I wasn't willing to order expensive food, and it adds up to a place that I pretty much despise.
So there you have it. Forget the Hopleaf. Go to the Maproom.
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