Old Town Neighborhood Profile and MLS Listings

Tree-lined streets and cheerful little alleys set the tone for this area of Chicago real estate. Old Town condos, townhomes, and apartments are among some of the most coveted in the city because of the area’s ideal location and bustling night life. Because of the diversity of property in the area, Old Town real estate can range drastically. Large single-family greystones can be in the millions, while smaller condos can still be found in the mid $300’s.

Originally a trading post for several Native American communities and later the home of Chicago artists and beatnik musicians, Old Town stays true to its origins. Eclectic boutiques, unique home décor shops, restaurants and bars fill this neighborhood with charm and convenience. Old Town, like many Chicago Neighborhoods, has a nebulous border. It is generally considered to be the area between Division to the south, Armitage to the north, Clark to the east, and Larrabee to the west.

Tourists and Chicagoans, alike, clamor to Wells Street on the weekends to enjoy the restaurants, bars, and, of course, the comedy. Home to Second City, the comedic birthplace of many a Saturday Night Live cast members, Zanies Comedy Nightclub, and the Red Orchid Theater, Old Town is a cherished piece of the Chicago performing arts scene.

In the summer, Old Town is particularly active, as Orso’s beer garden opens and the annual Old Town Art Festival, one of the oldest in country, attracts visitors from all over. A jury of curators, artists, and gallery owners determine which 250 artist from a variety of genres will be showcased each June. Equally as enjoyable is the September open-air wine market, Wine Crush in Old Town, where the streets of Old Town flow with libations from cellars all over the world. Wine tasting demonstrations makes vintners out of the even the greatest of novices.

Getting around Old Town is relatively easy on foot, as it is one of the smallest neighborhoods in Chicago. Transportation to other parts of the city is also a breeze, as the Red, Brown, and Purple CTA lines pass through Old Town. CTA buses take you east and west, and taxis are always readily available.

Old Town has become a popular landing spot for affluent families, as the large greystones can have as many as 7 bedrooms. Students in Old Town typically attend one of the following schools: Catherine Cook Elementary, Catherine Ferguson CPC, Cornerstone Academy, Franklin Elementary Fine Arts Center, George Manierre Elementary, Immaculate Conception School, Ruben Salazar Bilingual Education Center, and Schiller Elementary School.