Old Town is boardered by Armitage Avenue on the north, Division Street on the south, Clybourn Avenue on the southwest, Larrabee Street on the west and Clark Street on the east. Considered a hippie neighborhood in the 1960s, Old Town is home to Second City, the place where comedic giants like John Belushi, Bill Murray, and Gilda Radner got their starts.

Housing in Old Town is mostly vintage. There is a nice mix of cottages, row houses, condos, and two-flats. The Old Town Triage is a historic section of roughhouses on cobblestone streets that gives people a flavor of old Chicago. A popular community event in Old Town is the Annual Wine Crush that offers wine tasting and live music in a festival environment.