Old Town Neighborhood Guide

Old Town sits just north of downtown Chicago on a stretch of leafy, rehabbed rowhouses and stoops that give the neighborhood a storybook quality rare this close to the city core. It has long been anchored by Second City, the legendary comedy club on North Wells Street that has shaped American comedy for decades, and that creative energy still flavors the blocks around it. Wells Street patios fill up quickly on warm evenings, the Red and Brown Line stops keep the rest of the city accessible, and the annual Old Town Art Fair draws crowds that remind you the neighborhood has genuine cultural roots. The flip side is that proximity to a busy bar and entertainment corridor means weekend noise, parking headaches, and a 'local' spot that may not feel so local when comedy tourists are in town. Rent has climbed with the demand, but for residents who want walkable city life with character, Old Town still delivers.