With roots dating back to the mid-19th century, Old Town is historically “old,” but still young at heart. The community, just north of downtown, thrives on its myriad shops, restaurants, bars, and theaters; it’s easy to understand why people have decided to call it home for centuries.

 

The walkable, narrow streets and historic homes of Old Town give way to a string of high-rises lining the open vistas of lake and parkland. Home to a variety of comedy venues, shops, and a mix of old taverns and modern bars, the tiny neighborhood also packs its fair share of entertainment.

 

 

While it's primarily composed of tranquil residential blocks lined with low-rise, Victorian buildings, the neighborhood is more active in the Old Town Triangle District to the north, Division Street commercial areas to the south, and populated Wells and Clark Streets running through its core.

 

 

Old Town springs to life with specialty shops full of handmade goods, music and books, spices, and cigars; coffee shops and family-owned restaurants; and a mix of seasoned taverns like Old Town Ale House and newer bars like Old Town Pour House. The Second City and Zanies Comedy Club also regularly welcome notable acts to the stage, so there are always new shows to catch for belly laughs.

 

 

Old Town's popularity stems from its close proximity to the lake and downtown Chicago. Aside from the Cabrini-Green redevelopment and some multi-story, mixed-use developments with luxury apartments and multi-family buildings in the works, new construction buildings are relatively rare, making it an exceptional spot for those who want a mellow place in the city to call home.

 

 

While not quite as new or pricey as nearby downtown neighborhoods, Old Town certainly still has a prime real estate portfolio. A diverse selection of brick townhomes, single-family homes, and vintage walk-up apartment buildings line its charming streets and condo units in high-rises that display sweeping lake views.

 

 

Simply meandering the streets en route to the nearby lake can be a treat for Old Town residents and visitors, and its distinctive architecture is a natural draw for those who appreciate being surrounded by history. Many of the city’s oldest Victorian-era buildings, such as St. Michael’s Church, which survived the Great Chicago Fire of 1871, are still staples of the community.