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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.

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.

Commute Times

The Loop          by train,          by car

Merchandise Mart          by train,          by car

Union Station           by train,         by car

Millennium Park          by train,           by car










East to West Clark Street to Halsted Street
North to South North Avenue to Division Street
Nearby Neighborhoods Lincoln Park, Near North Side, Gold Coast, and Streeterville

Closed Prices:

$125,000 to $5,100,000

Median Sale Price:


Average $ per sq ft:


Association Fee Ranges:

$744, $0 to $562, $0 to $2548/mo

Square Footage:

375 to 8500 Sq. Ft.


Attached Home (Condo, Townhouse, Loft, etc.), Single-Family Home

Year Built:

Current Prices:

$139,900 to $4,000,000

Quick Facts



0 to 6 Bedrooms

1 to 8 Bathrooms

1870 to 2021


From artsy to well-off, the neighborhood’s inhabitants have changed over the decades. Today, they’re generally well-educated and cultured with a considerable income. However, residential properties also tend to be slightly less expensive than other neighborhoods in Chicago, so it is also affordable.


An educated and affluent population with a love for the European neighborhood vibe.

Peaceful, private streets with a few commercial stretches.

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.


A lively atmosphere with some of the best comedy in town.

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’s always new shows to catch for belly laughs.


A welcome escape from the chaos of urban expansion.

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.


Affordable walk-ups and high-rise condos with lake views.

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.


Charming backdrops and close proximity to the lakefront.

Simply meandering the streets enroute 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.


The Red Line, Brown Line, and Purple Line all run through Old Town, making it simple to get to work in the Loop or head north to watch the Cubs play at Wrigley Field. There are numerous bus routes that can take you anywhere you want to go, with the main east/west lines running along Division Street on the south side of the neighborhood and North Avenue closer to Lincoln Park. The area is generally walkable, and its proximity to Lincoln Park and the Lakefront Trail encourages cycling. Street parking is certainly easier to come by than in Downtown neighborhoods, but finding a spot on main streets during peak hours can still be difficult. Driving home from the Loop during rush hour can take three times as long as it should because Downtown traffic tends to spill into the neighborhood, making locals grateful for the Brown Line!

Public Transport Passenger


Old Town Art Fair

Voted the #1 Art Fair in America. Chicago's original art fair since 1950. The Old Town Art Fair is located in the Old Town Triangle Historic District. The event features over 200 artists, a garden walk, live music and food.

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