With gorgeous architecture, quaint tree-lined streets, and historic charm, Old Town is one of Chicago’s most desirable residential areas.
The neighborhood is a culinary, shopping, and entertainment hotspot. In an ideal location, residents are just one mile from the Loop and walking distance to lakeside beaches. And, with great public transit (CTA Red, Purple, and Brown lines), your next Chicago adventure is just around the corner!
Old Town Neighborhood Guide
A hippie stomping-ground in the 1960s, today a creative spirit lives on in Old Town’s innovative businesses, artistic residents, and world-famous comedy.
The neighborhood’s dining scene is known for its family-owned restaurants and the sheer variety of options. Anything from barbecue ribs, sushi, steak frites, to pasta and pizza can be found in Old Town.
Some local favorites include Topo Gigio, a romantic Italian restaurant which was served the neighborhood for over 30 years. Twin Anchors is a BBQ joint famous for serving Frank Sinatra in the 1930s. For delicious French pastries, check out La Fournette.
Old Town’s tendency for long-standing establishments continues in its bar scene. The jazz-filled Old Town Ale House has been around since 1958. The dive bar has been frequented by famous locals including Roger Ebert and Second City comedians. Craft beer fanatics will find solace in the Old Town Pour House. The bar features a massive beer list, classy wood interior, and high-end bar food.
Old Town is an entertainment hotspot — residents and visitors love Old Town’s theater, comedy, and art scene. Theater companies include the renowned Steppenwolf and Red Orchid Theaters, putting on heady and moving productions.
Old Town may be best known for its comedy, including the world-famous Second City, with uproarious improv comedy. The company, which also offers all-ages classes, launched the careers of comedy greats including John Belushi, Bill Murray, Tina Fey, and Steve Carell. Zanies Comedy Club is a go-to for stand-up.
Each June, Old Town shows off its artistic spirit in one of America’s oldest art fairs. The fair features more than 250 artists in a huge variety of disciplines. Old Town also has a healthy shopping scene, with a number of innovative family-owned boutiques with wares ranging from cigars and ice cream to designer clothes and rare spices.
Parks and Recreation
In the summer, Old Town becomes a beach town. Two of Chicago’s nicest beaches (North Avenue and Oak Street beaches) are within walking distance. Both offer beautiful city views, beachside cafes, great swimming areas, and other amenities.
And just to the north lies all the splendor of Lincoln Park, including the free Lincoln Park Zoo. Chicago’s largest public park, Lincoln Park, offers sprawling green spaces, lovely harbors, and a miles-long beachside trail perfect for biking and jogging.
Old Town History
Early Settlement (1830-1900)
As the area was settled in the 1830s by German farmers, the Old Town area was known for decades simply as the “Cabbage Patch”. These industrious Germans managed to turn what was swamp into productive farmland and built the awe-inspiring St. Michael’s church.
St. Michael’s was one of the few major structures spared from the flames of the Chicago Fire and it remains active to this day. Sitting on Chicago’s then-northern border, the community began to be known as “North Town”.
Growth Years (1900-1950)
The 1900s saw Old Town rise to prominence, even at one point being a hub of the burgeoning movie industry. In these years, a lucky Old Town resident could see Charlie Chaplin and other stars walking down their streets. In 1924, Old Town became the home of the first American gay rights organization. In 2015, founder Henry Gerber’s home became a national historic landmark.
Artists flocked to the area in the 1920s and 1930s and the streets filled with writers, bohemians, and revolutionaries. The neighborhood’s final name came from a 1940s art fair, named “Old Town Holiday”, which is still an annual event.
Countercultural Old Town (1950-1970s)
With many of the affluent residents leaving the area in the 1950s and 1960s for the suburbs, Old Town became Chicago’s hippie neighborhood. Head shops, music clubs, and gay and lesbian bars filled empty storefronts.
Chicago institution Old Town School of Folk Music was founded in the area in 1957. Early performers included Pete Seeger, John Prine, Mahalia Jackson and Roger McGuinn of the Byrds. The school has since moved to Lincoln Square and Lincoln Park, where it continues to empower students and artists.
Old Town Homes
Old Town offers a variety of housing options at a variety of price points. The neighborhood’s charming tree-lined streets are filled with examples of Victorian-era buildings, including historic mansions, rowhouses, and greystones. Newer construction is also available, including condominiums with sweeping lake views and modern three-flats. While multi-million dollar mansions are available, Old Town is more affordable than the swanky neighborhoods at its borders.
With its historic charm, old-world feel, and beautiful homes, Old Town is a truly classic Chicago neighborhood. Come walk through the iconic gates and take a look!