The Run Down
We've planned a whole night, all within a one-block radius right off the Damen Blue Line Station. It starts with New Haven-style pizza at a brewery with a 20-year history in Wicker Park. You'll then head around the corner, where if you can time it right, you'll have drinks and maybe a bit of karaoke at this bar with an early 20th-century vintage style. The last stop is a speakeasy behind a record store where you'll end the night with a giant cocktail served in a gauntlet.