Old Town

A lively neighborhood with iconic nightlife

Welcome to Old Town

Old Town is a quaint neighborhood with a vibrant atmosphere and a unique identity.  Charming streets integrate to connect the quaint cafes, vintage boutiques, and award-winning restaurants. Known for its historic architecture, Old Town allows walkable ease, encouraging locals to stroll among the residential areas and admire the classic Chicago designs. Two-flats and Alder and Sullivan-style row houses dominate the architecture offering a timeless character. 

As the birthplace of modern American improv, Old Town has earned its reputation for having the best late-night attractions. Comedy clubs are nestled within the community, making history as the starting ground for some of the best comedians in the industry. Aside from the comedy clubs, cocktail bars and supper clubs allow for a laid-back evening that holds old-world glamor. Once a popular art colony, creativity is embedded in this lively community.

What to Love 

  • Legendary comedy clubs that launched major comics 
  • Dynamic nightlife attractions
  • A charming, upbeat atmosphere

Local Lifestyle

The atmosphere found within Old Town is the result of respecting the old and embracing the new. Historical landmarks dot the streets. However, new life is constantly being found within the district. Never one to grow stagnant, Old Town has endured the rich history of Chicago with new energy by promoting working professionals. 

Old Town has a newer wave of history, providing its own unique form of legacy: comedy. Major comedians have passed through the district in the early years of their careers, allowing Old Town to be the breeding ground for comedy legends that later wrote award-winning productions. The amount of comedy clubs that have launched careers means comedians and artists flock here to get their start. 

Other residents can enjoy the shows, see up-and-coming comics, and appreciate a great night out. Young artisans, such as chefs, painters, sculptors, and designers, are also thrilled at a chance to make their mark. The vibrancy of the neighborhood allows for a steady stream of new life. 

Dining, Entertainment, & Shopping

It doesn’t get much better than Jeni’s Splendid Ice Creams. With a series of her ice cream parlors opening across Chicagoland, Old Town residents can experience the satisfaction of having a scoop of Jeni’s ice cream as they stroll through the neighborhood. 

Reminiscent of an artisanal general store, Judy Maxwell offers curated nostalgia in the form of luxury notebooks, childhood candy bars, and other whimsical products to draw out the inner child.

Nothing hits the spot like a good pizza restaurant. Happy Camper is a relaxed setting where diners can enjoy quality pizza and beer surrounded by repurposed airstream trailers. Kanela Breakfast Club is a vibrant cafe serving greek influenced cuisine and organic produce. Their breakfast has been rated one of the best in Chicago, with their menu made up of dishes packed with flavor.  

Following in the footsteps of its parent restaurant Au Cheval, Small Cheval carries the legacy of Au Cheval’s famous cheeseburgers to Old Town. The cuisine of Americana diners, such as milkshakes, burgers, and fries, is served with quality ingredients. 

Nookies on Wells is a family-owned restaurant serving breakfast all day. Named after the nickname “breakfast nook,” this local spot seeks to replicate the cozy intimacy of the breakfast table, serving comforting classics with innovative twists. 

Things to Do 

Zanies Comedy Night Club and Second City are historic spots where comedy legends are born. Residents appreciate the chance to see fresh new comics and have an amazing night in two of Chicago’s best clubs. Over a weekend, an estimated 30,000 Chicago natives flock to the Old Town Art Fair. On average, nearly 200 artists participate in sharing their craftsmanship, eager to offer their work to the public.

The curved structure of North Avenue Beach creates an enclave where residents can relax on sandy beaches and enjoy the clear waters of Lake Michigan. In the summertime, locals adore the chance to sunbathe, play volleyball, and swim in the water. 

History is brought to life at the Chicago History Museum. Residents and members can explore the photographs, exhibits, and archived news footage, seeing the development of their city. Established in 1852 by the Diocese of Chicago, St. Michael Catholic Church is one of Chicago’s oldest and most well-respected Catholic churches. Even those who are not within the Catholic Church are drawn to the building for its architectural heritage.


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