Booze Box

A small subterranean spot for draft sake with a very literal name. 823 W. Randolph St. Website

The Brass Monkey

This ’70s-inspired cocktail explosion is one funky monkey. 401 N. Morgan St. Website

The Drifter

A Prohibition-style speakeasy that actually was once a Prohibition-era speakeasy. 676 N. Orleans St. Website

Lost Lake

Don’t get too attached to the banana dolphin in your daiquiri—it makes for a tasty snack after you down your drink. 3154 W. Diversey Ave. Website

Two Zero Three

Coffee by morning, wine by night, and a buzz at any hour. 203 N. Wabash Ave. Website