Inner Page Header


Inner Page Header

Homepage Header


Main Content

Home » Uptown


Uptown is home to some of Chicago’s most iconic theaters and concert venues. A highly anticipated event here is the reopening of the iconic Uptown Theater after its renovation. This locale also boasts some of the best real estate opportunities outside of the Chicago Loop. Whether you choose a luxurious loft overlooking Lake Michigan, a townhome close to the famed entertainment district or a quiet suburb-style single-family house, Uptown is sure to delight.

Uptown bears a proud heritage as a prominent entertainment district. It distinguishes itself as a community where culture thrives. This sought-after lakeside neighborhood is roughly a 20- to 30-minute drive away from the Chicago Loop with its convenient access to Lake Shore Drive.

Uptown is one of the most intriguing places to find a home in Chicago’s Far North Side. The area is primed for a renaissance with notable restoration projects for some of its palatial, art-deco style theater buildings.

A brief history of Uptown

Uptown has a rich history as one of Chicago’s most popular entertainment hubs throughout most of the 20th century. Prominent names in the history of show business have contributed to its starry reputation, including Charlie Chaplin and Frank Sinatra.

Uptown was also well-known as a resort town for residents of downtown Chicago. The construction of a railroad station in 1900 made the neighborhood more accessible, spurring a population boom that turned a former suburban enclave into a thriving urban center.

Communities from a variety of cultural backgrounds began arriving in Uptown from the 1950s to the 1980s following a brief decline in the post-World War II years. The influx of multinational communities during this period helped shape Uptown’s culture into the vibrant mix that it is today.

Uptown, Chicago real estate

Residential real estate in Uptown comprises a selection of townhomes and condos in mid-rise buildings.

Urban luxury here can be found closer to the lake where most of the neighborhood’s new high-rise construction projects are concentrated. From here, lakeside attractions like Montrose Beach, Margate Park Field House, and the Lakefront Trail are a brief walk away.

The southern part of the neighborhood also features modern condominiums that boast of vintage penthouses and seamlessly integrated corner stores.

For a more suburban feel, the northern part of Uptown features single-family houses on large lots where gardens and even street parking are not a problem.

Buyers looking to own a piece of Chicago history can explore the Buena Park, Margate Park, Uptown Square, and Sheridan Park districts for available 19th-century homes.

Lifestyle in Uptown

When you move to Uptown, these exceptional community highlights will be part of your regular routine:

    • Where to eat

Flavorful Chinese, Vietnamese, and Thai cuisine line the Asia on Argyle district. The Ethiopian restaurant Demera is also a must-visit dining destination.

    • Local schools

Administered by the Chicago Public Schools district, the following schools serve the Uptown Chicago youth:

      • Pre-K to 8: Courtenay Language Arts Center, McCutcheon Elementary School, Goudy Technology Academy, Brenneman Elementary School, Disney Magnet Elementary School
      • 9-12: Uplift Community High School


    • Signature attractions

What Uptown may lack in iconic shopping destinations and experiences, it makes up for in legendary performance venues. Visit the Lawrence and Broadway entertainment row to catch shows on historic stages such as the Aragon Ballroom, Green Mill Cocktail Lounge, and Riviera Theater. Watch out for the return of the celebrated Uptown Theatre, which is gearing up for a major restoration.

Cain Chicago Residential connects real estate buyers with the best leads and opportunities for Uptown, Chicago homes for sale. Get in touch with George Cain today at 773.818.9005 or GeorgeCain(at)CainChicago(dotted)com.

Sorry we are experiencing system issues. Please try again.