Broken Shaker

The boundary-pushing award goes to this Miami import, where bartenders use everything from pork bitters to porcini mushrooms in the 15 original cocktails. Though the Chicago-inspired concoctions sometimes miss the mark, the daily punch—on one recent visit, a combo of blood orange and rum—always scores. The bar is inventive enough to entertain both trend-chasing River … Read more

Breakroom Brewery

It ain’t the out-there Band of Bohemia (No. 4), but Breakroom exceeds expectations with its broad beer menu, impressive hand-carved bar from the woodworking shop next door, and more than enough room for you. And your date. And your 12 closest friends. 2925 W. Montrose Ave., 773-564-9534 Crowd Neighborhood couples on laid-back date nights Food … Read more