Old Town, Chicago

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With a history of diverse inhabitants with backgrounds ranging from artsy to affluent, Old Town has been home to a wide range of residents through the years. The boundaries of Old Town, though still not a true legal entity in the City of Chicago, is normally described as Armitage Avenue at it’s Northern most point, Division Street on the South, Clark Street on the East and Halsted Street down to Clybourn Avenue on the West.


Like most of the area we now know as Chicago, Old Town was originally home to Native Americans, specifically the Potawatomi, Miami and Illinois tribes. In the mid 1900s the land was settled by German-Catholic farmers who planted many crops in the area including celery, potatoes and cabbage. During World War II, the area between North Avenue, Clark Street and Ogden Avenue which made up a triangle, was designated for neighborhood defense. Many of the streets alleys avenues and even some buildings through Old Town escaped the carnage of the Great Chicago Fire and don’t follow Chicago’s, “grid system.” Through the years following World War II, Old Town has functioned as a cultural center for art, music and entertainment.


Today Old Town has experienced gentrification throughout. Old Town has become a residents dream with many housing options from Condominiums, old and new, to luxury apartment buildings. The neighborhood hosts a wide variety of street festivals in the summer months and is home to many of Chicago’s iconic comedy venues including Second City and Zanies. Shopping, restaurants and nightlife have found a permanent home in the area with many being smaller family owned businesses.


Perhaps dating back to just after World War II, the Old Town Art Fair, normally held in June, is put on by the Old Town Triangle Association. The event is one of Chicago’s best, drawing artists from across the country displaying and selling their creations with a backdrop of great music and food. Year round the neighborhood hosts great restaurant, bars and nightlife to fit anyone’s desires. A walk down Wells Street in Old Town can easily eat up an entire afternoon with the many specialty shops, and restaurants to stop in to.

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