Chicago’s architectural landscape includes a rich history of luxury apartment buildings dating back to the late 19th century, as detailed in a new publication exploring the city’s prominent residential structures. The book, a collaborative effort by real estate developer and historian Perry Casalino and lawyer and historian John Graf, aims to illuminate the evolution and significance of these residences in Chicago’s urban development.
According to the authors, Chicago's first recognized luxury apartment building was the Beaurivage, completed in 1876 at the corner of Michigan Avenue and Van Buren Street. Designed by architect James Rowland Willett, the six-story brick-and-stone structure marked a shift toward elegant urban living. Though the Beaurivage was demolished in 1908, the book documents over 120 additional luxury buildings constructed in the following three decades. The Mentone, built in 1883 at 650 N. Dearborn Street, remains the oldest surviving example and currently houses businesses and offices.
The volume dedicates considerable attention to the South Side of Chicago, showcasing more than 75 pages on the area’s luxury apartments, while the North Side is covered in about 40 pages and the West Side receives more limited focus. Among the West Side examples is the Ashland building at 36 S. Ashland Avenue, a five-story triangular structure, and a sizable edifice at 301-315 S. Halsted Street. The book also highlights the Brewster Apartments at 2800 N. Pine Grove Avenue, originally called the Lincoln Park Palace Apartments when finished in 1896. Notably, this nine-story building once featured a striking central atrium and was home to Charlie Chaplin for a brief period.
Other notable properties include the Lessing — later renamed the Commodore — located at the corner of Broadway and Surf Street. Initially named after German philosopher Gotthold Ephraim Lessing, the building contained amenities such as a ballroom and now operates as condominiums. Many luxury apartments covered in the book boasted leisure facilities including billiard rooms, bowling lanes, retail spaces, and gardens, reflecting the era’s emphasis on upscale communal living.
The authors acknowledge the limited archival imagery of interior spaces, which restricts insight into the private lives of past residents. Nonetheless, they assert that these buildings played a foundational role in shaping Chicago’s enduring affinity for tall, refined residential structures, influencing perceptions of urban luxury.
When discussing the public’s enduring fascination with such residences, Casalino suggests it stems from admiration for Gilded Age architecture and a complex mixture of societal intrigue surrounding wealth and its associated lifestyle. Graf adds that the appeal likely combines escapism, aspirations for upward mobility, and the notion that wealth can resolve life’s difficulties. Local real estate commentator Bob Goldsborough also notes that American society demonstrates a strong interest in observing upscale living, interpreting it both as aspirational and entertaining, facilitated by widespread access to real estate imagery online.
Today, Chicago’s luxury apartments continue to be a hallmark of the city’s skyline. For instance, One Bennett Park at 451 E. Grand Avenue offers modern high-end living with a one-bedroom, one-bath unit currently listed for $4,300 per month, underscoring the ongoing demand for upscale urban residences.