Old Town

Old Town, Chicago, IL sits between North Avenue and Division Street, stretching west from the lakefront toward Larrabee Street. Victorian-era rowhouses and Italianate brownstones line streets shaded by mature elms. Walk down Lincoln Avenue or Crilly Court and you'll find narrow coach houses converted into single-family homes, wrought-iron fences separating tiny front gardens from brick sidewalks. The Old Town Triangle Historic District preserves some of the city's oldest residential architecture—buildings that survived the Great Fire and define what Chicago looked like in the 1870s.

Second City anchors the neighborhood on North Avenue, where comedians like Tina Fey and Stephen Colbert launched careers. Wells Street runs through the heart of Old Town with restaurants like Twin Anchors (order the ribs), Old Town Social, and Topo Gigio serving Italian since 1986. The Old Town School of Folk Music on Armitage hosts concerts and classes seven nights a week. You're three blocks from Lincoln Park's lakefront trails, the zoo, and North Avenue Beach. The Brown and Purple Line stops at Sedgwick put you downtown in twelve minutes.

Apartments for rent in Old Town range from vintage walk-ups with hardwood floors to newer mid-rise condos along Wells Street. Homes for sale in Old Town include restored Victorian single-families, brick townhomes with original details, and occasionally a coach house conversion. The market moves fast—properties here attract buyers looking for historic character in a walkable neighborhood with immediate lakefront access. If you want established architecture, a real main street, and comedy club proximity, Old Town real estate delivers that without compromise.