Old Town


Home to one of Chicago’s best street festivals, and one of the Midwest’s best art fairs, Old Town knows how to bring fun and culture together like no other!  And speaking of fun, the main strip down Wells Avenue is home to a series of comedy clubs – the crowning achievement being Second City.  No other group had had as large an impact for as long a time as the Second City, with cast members through the years ranging from Murray to Farley to Fey and Poehler.

In addition, Old Town is the namesake to the original Old Town School of Folk Music, located on the north end off the neighborhood on Armitage Avenue.  Similar to the Second City, this venue has introduced the world to some very influential musicians in their own right.

And – if that wasn’t enough activity for you – the restaurants range from long-time Chicago establishments to trendy new clubs.  All catering to a collection of people who enjoy the finer things in life.

In addition to the Old Town Art Fair, a major Summer highlight is the Chicago Air and Water Show which brings one million people to the shoreline to watch aerial demonstrations of some of the latest in aviation technology.






North – Lincoln Park
South – Downtown Chicago
West – Wicker Park
East – Gold Coast

Zip Code(s):


Public Transportation:

  • CTA: Brown Line (Sedgwick), Purple Line (Sedgwick), Red Line (Clark/Division, North/Clybourn)

Main Roadways:

  • Lake Shore Drive
  • Clark Street (N/S)
  • Division Street (E/W)


Old Town Real Estate Listings


Natalie Smith

Natalie Smith

@properties Real Estate Agent

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