Old Town

Their influence and artistry can be seen throughout the neighborhood.

Welcome to Old Town

A historic and eclectic neighborhood, discover Old Town Chicago real estate!


Old Town, as its name suggests, has always been one of Chicago’s most historic and eclectic neighborhoods. German immigrants initially settled the area in the early 19th century; farming what was previously considered swamp land. In those days, the area was known as “The Cabbage Patch.” 
In the late 20s and early 30s, Old Town began to see an influx of artists and artisans. Multidisciplinary artists, Sol Kogen and Edgar Miller purchased old buildings and turned them into live-work spaces for artists, inviting more artists to come and create. Their influence and artistry can be seen throughout the neighborhood.
By the 1950s “North Town” as it had come to be known, became a predominantly Puerto Rican enclave; during the 60s it was popular with the Hippie and Yippie counterculture, and during the 60s & 70s it was the center of Folk Music and Comedy in Chicago. 
Perhaps the area is best known for its annual “Old Town Art Fair”, held every summer since 1950, in the historic triangle district. The Art fair, originally dubbed “Old Town Holiday” became a popular attraction for the neighborhood. Eventually, the name “Old Town” was adopted by the community as its official name. To this day, the annual “Old Town Art Fair” attracts over 250 artists nationally, and has been voted the #1 Art Fair in America.


Only two miles from the Loop, Old Town sits just west of the Gold Coast neighborhood, and south and east of the Lincoln Park neighborhood. The official boundaries are Division to the south, Halsted to the west, Clark St. to the east, and it is arguable as to whether North Ave. or Armitage constitutes the northern boundary. Old Town Chicago real estate for sale offers the perfect central location in the city. 

The Vibe & Housing Style

Famous for its distinctive architecture and European character. The brick alleyways and narrow, tree-lined streets, which pre-date the Chicago Fire, are lit with old harp-style street lamps and gaslight lanterns. St Michael’s Catholic Church is one of only 7 churches to have survived the Chicago Fire. As Old Town was never actually legally defined by boundaries, residents claimed that only those who could hear the sound of the bells of St. Michael’s actually lived in Old Town. Chicago's real estate agents,  the Choose City Living team are ready to help you find your home in this unique community.
The neighborhood is a mix of baby boomers, young families, and young professionals, who love Old Town for its eclectic, artisanal vibes and unique character. 
Old Town retains that early connection with art and artistry, and the original “handmade homes'', crafted by prominent artists of that period, are still lovingly maintained as private homes. Neighborhood residences on the Old Town Chicago real estate market vary widely in architectural style, featuring everything from Victorian and Renaissance Revival brownstones to 19th-century row homes, and charming brick and frame cottages, to mid-century townhomes, and High Rise condominiums.

Local Lifestyle

This Chicago neighborhood caters to a broad range of tastes and interests. Culturally minded individuals seeking a unique and tranquil city neighborhood, are drawn to the meandering residential streets lined with vintage homes of all types. 
Old Town’s lively commercial district provides plenty for residents and visitors to do. Wells Street offers an entire day's worth of shopping, eating, and drinking, and at night, some of the best entertainment in the city can be found at Zanies and The Second City. 
For those looking to take a break from urban life, nearby Lincoln Park, Lincoln Park Zoo, and North Avenue Beach offer an entirely different dimension. Enjoy the lakefront walking paths, bicycling, kayaking, beach volleyball, or sunbathing in the summer. Take a walking tour of the surrounding neighborhoods. Shop for exquisite produce and select meats and baked goods at Green City Market farmers’ market in Lincoln Park.

Dining, Entertainment & Shopping

For a relatively small neighborhood, Old Town has a big selection of top-notch dining, shopping, and nightlife options. For restaurants, Wells Street favorites include legendary Neapolitan pizzeria Gallucci Pizzeria Napoletana, upscale Japanese and Sushi restaurant Kamehachi, and a fine Italian eatery Topo Gigio. Off Wells Street, locals love barbecue spot Twin Anchors on Sedgwick for its delicious food and fascinating Chicago history as a former favorite of legendary crooner, Frank Sinatra.
Of course, no trip to Old Town would be complete without a visit to one of its famous comedy clubs The Second City or Zanies, with stand-up comedy and improv shows throughout the week. 

Old Town is also a significant destination for shoppers who prefer artisanal and boutique shops. Local favorites include the women’s clothing boutique Sara Jane and one-of-a-kind, family-owned, and quirky florist Green Inc. For residents with a passion for food, Wells Street has several unique food specialty shops, including Old Town Oil, cooking spice retailer The Spice House, chocolatier and candy maker, The Fudge Pot, authentic French bakery La Fournette and upscale grocer Plum Market.
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