Old Town, a Chicago Neighborhood Guide

The streets of Old Town are charming and tree-lined; the homes lining the streets vary from townhomes to single-family homes, all of which have distinctive architecture and lovely brick construction. It is a pocket of residential calm among the high-rises of the Loop. Many of Chicago’s Victorian-era buildings are in Old Town; in fact, one of the few buildings to survive the Great Chicago Fire of 1871, St. Michael’s Church, is located here. Certainly, the area has historical appeal; this fact was formally recognized when the Old Town Triangle was designated a Chicago Landmark on September 28, 1977.

The inhabitants of Old Town are generally affluent; although properties are not as expensive as in the nearby Gold Coast neighborhood, they are certainly prime real estate and are mostly inhabited by professionals and families.

Although historical and largely residential, Old Town does have a lively center with several entertaining establishments. Second City’s performance group is based here, as is a branch of the famous Steppenwolf Theater and the Zanies comedy club.

Boutiques, restaurants, clubs and coffee shops keep locals and tourists entertained and fed as they wander through the streets of this Chicago treasure. Old Town is one of the city’s oldest neighborhoods with its roots firmly planted in Chicago’s history, but it has so much to offer that it will surely be a well-loved part of the city’s future.

Annual Art Fair

The Old Town Art Fair is held annually in June. It is one of America’s oldest art fairs, getting its start in 1950. During its first eight years, the general public was welcome to submit art, and thus the fair included amateur as well as professional pieces. In 1958 a committee was formed to regulate submissions, and a jury was given the task of choosing a balanced mix of art in all genres and mediums and to raise the standards by which art was accepted into the fair.

At the fair, the work of over 250 artists is on display, in all mediums including drawing, painting, photography and more. The art is chosen by a jury made up of artists, gallery owners and even museum curators. The Art Fair also includes live musical performances. Other highlights include a Garden Walk, a tour of the historic neighborhood and a children’s activity area.
The suggested donation is $5.00 and all proceeds benefit local youth groups, schools and neighborhood preservation projects. It is produced by the Old Town Triangle Association and involves the help of over 700 volunteers from the neighborhood. The Art Fair is held rain or shine.


Shopping in Old Town is a unique experience; the majority of shops in this neighborhood are boutiques rather than well-known chain stores. Therefore, each and every store is cozy, intimate and filled with one-of-a-kind goods.

For apparel, try Sara Jane, Etre, Occhiali and Vagabonds; all of these are boutique-style shops with beautiful clothing for women and men. Shoppers are given personal attention and the atmosphere in these shops is peaceful, giving a new dimension to the idea of retail therapy.

Old Town offers stores for house and home as well; in addition to a branch of the popular Pier 1 Imports, there are smaller shops such as Design Source, Inc., Calico Corners and Modern Home Furnishings.

There are several specialty shops as well in Old Town; for handmade paper and cards, try Pulp & Ink or Eco Fields. For music and books, try Barbara’s Bookstore. One of the local favorites is The Spice House. A world of heady aromas, this shop sells hand-selected and hand-prepared spices that range from everyday American, Cajun and barbecue spices to truly exotic seasonings from Greece, Turkey, Scandinavia and even Thailand.


When it’s time to eat, Old Town delivers. There are restaurants unique to Chicago, such as Sauce, which serves American Eclectic food, Bistrot Margot for French cuisine, Dinotto Ristorante for Italian cuisine and Salpicon for hearty Mexican fare.

Some well-known chains can be found here as well; try the Flat Top Grill for Asian-inspired stir-fry or the Adobo Grill for stir-fry of a more Mexican flavor.

Sushi is a favorite among Old Town locals; Kamehachi, Mizu and Café Sushi are slightly upscale sushi bars; head to any of these for sophisticated décor and a genuine sushi meal.

After hours, Old Town’s bars and clubs are plentiful. Wells on Wells, across the street from Second City, is a popular destination for those who want to meet the cast after a show. Hobo’s and the Old Town Ale House are laid-back and frequented by regulars, while Spoon is a classy, lively joint where people can lounge, dance and meet all kinds of people.


Old Town is located north of downtown Chicago, nestled between the Gold Coast and Lincoln Park. This is a quiet, tree-lined neighborhood, but in addition to the historic residential qualities, Old Town also offers theaters, restaurants and clubs.

Old Town Chicago Neighborhood Map


Old Town is indeed old. Originally settled in the mid 19th century by German-Catholic immigrants, the neighborhood got its name and became closer knit during World War II, when Chicago’s Civil Defense Agency delineated a neighborhood defense unit. The unit was made up of a triangular area bounded by North Avenue, Clark Street and Ogden Avenue. This area was called North Town. North Town’s inhabitants felt a sense of continued connection even after the War ended and in the spirit of community, they began to sponsor annual fairs which they called the “Old Town Holiday.” In 1948 the Old Town Triangle Association was formed, and since then, the name “Old Town” has stuck; it is now the area’s official moniker.

Today’s Old Town is bordered on the north by Armitage Avenue, on the South by Division Street, on the east by Clark Street and on the west by Larrabee Street and Orleans Street. The neighborhood lies north of Chicago’s downtown and 40 years ago it was one of the city’s first areas to be gentrified.