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Neighborhood Spotlight: Uptown

Nestled on Chicago’s North Side lies the neighborhood of Uptown. This diverse community is known for its unique blend of cultures, lively music scene and stunning architecture. Uptown has a rich history dating back to the early 1900s and has undergone significant changes over the years. Today, we’ll dive into all Uptown has to offer. 

Courtesy of Thomas Hawk, flickr

A Brief History

In the early 1900s, the neighborhood became a summer resort town for those who lived downtown. However, with the city’s growth and industrialization, Uptown quickly became more densely populated with working-class and immigrant families. The neighborhood was also a hub for entertainment during the Roaring Twenties, boasting an array of theaters and music venues. 

The Aragon Ballroom, built in 1926, still stands today and has hosted some of the most iconic musicians of the past century, including Frank Sinatra, Nirvana and Prince. In the 1960s and 70s, Uptown transformed as many of the theaters were converted into concert halls for rock and roll bands. Today, Uptown is a vibrant community that continues to celebrate its diverse history while embracing new developments and growth. 

Culture and Entertainment

One of the main draws of Uptown is its thriving music scene. The Riviera Theatre, another historic venue, hosts a variety of concerts and events throughout the year. Meanwhile, the Green Mill Jazz Club, a speakeasy from the Prohibition era, has been a staple of the neighborhood since the 1900s and continues to attract international jazz enthusiasts. In addition to music, Uptown is home to several art galleries, theaters and cultural events. The Uptown Art Fair, held annually in August, features the work of over 350 artists and draws crowds of up to 400,000 people. 

Uptown is a foodie’s paradise, offering a diverse range of cuisines. Argyle Street is just one population location where residents can find a wide selection of cuisine, and it’s also the home to The neighborhood is known for its selection of Vietnamese restaurants, with some of the best pho and banh mi in the city. There are also several Ethiopian, Middle Eastern and Mexican eateries, as well as classic American diners and taverns. Favorite stops include Demera Ethiopian, Tank Noodle and Sun Wah BBQ. And for those looking for a night out, Uptown has a number of bars and breweries, including the favorite Half Acre Beer Company. The neighborhood is also home to the iconic Green Mill Cocktail Lounge, which has been featured in several movies and TV shows. 

Argyle Night Market, Courtesy of Kevin Zollkiewicz, flickr


Following the World’s Columbian Exposition and the turn of the century, the neighborhood experienced an architecture boom. Large and lavish buildings and landmarks began to fill the area, including the iconic Uptown Theatre. This majestic theater, which first opened in 1925, was once the largest movie palace in the country and is currently undergoing restoration. 

Another notable landmark is Essanay Studios, which operated from 1907 to 1916 and was responsible for producing early silent films with Charlie Chaplin. The studio’s former building still stands today and has been converted into apartments. Because of Essanay Studios, many actors resided close by on Castlewood Terrace – now a historic district – in ornately designed structures that still stand out from the rest of the neighborhood’s architecture. 

Uptown offers a wide variety of housing types throughout the neighborhood, from historical single-family homes to contemporary high-rise condominiums. The neighborhood’s architectural styles range from Victorian-era buildings to Art Deco and Mid-Century Modern designs. Between Montrose and W Lawrence Ave, Dover, Beacon and Malden Street provide the neighborhood with some of its most enchanting architecture, with many vintage homes often featuring unique architectural details such as stained glass windows, ornate moldings and original hardwood floors. 

Uptown is a neighborhood with a rich history and a bright future. With its diverse community, lively entertainment scene and stunning architecture, there’s always something new to discover in this vibrant corner of Chicago. Whether you’re a music lover, foodie or history buff, Uptown has something to offer everyone. If you’re interested in searching for your own place in Uptown, feel free to contact someone from our team. And stay tuned for more neighborhood spotlights on our blog!