Old Town was settled in the mid 1800's when Chicago absorbed a wave of German farmers and semi-skilled laborers who were fleeing Germany in search of a better life. During the 1960's, Old Town became the center of the Bohemian renaissance movement. In recent years, the development of several highrises and the award winning conversion of the Dr. Scholl shoe factory into luxury residential lofts (Cobbler Square) coupled with the emergence of new town homes, has brought upscale retail and dining establishments with a vengeance.

The annual Old Town art fair has grown into the largest juried art fair in the country, and Wells Street, offers upscale shops to satisfy all tastes. Nearby on Halsted Street is the impressive new home of the Steppenwolf Theater, the epitome of storefront or, specifically, church basement theater, all grown up. Today, Old Town remains one of the most lively and picturesque neighborhoods in Chicago and of course, it is the home of the world famous Second City.