Designed in 1886 for an executive of International Harvester by the famed H.H. Richardson, the Glessner House is a rare survivor along South Prairie Avenue, once the most fashionable address in the city. Now a museum, the house has many of the original furnishings from the family who built it. In order to retain the integrity of Richardson's design, the museum purchased a brick wall of the neighboring building before its demolition to preserve its sheltered courtyard.

Designed by Cobb & Frost in 1886 for the president of the Rock Island & Pacific Railway, the Cable House is one of only a few houses that remain in the area which once housed many of the city's greatest mansions—now dominated by skyscrapers. It was purchased in 1902 by Robert McCormick to become his son's residence. Today, it is the headquarters of Driehaus Capital Management, owned by Richard Driehaus, the noted preservationist and philanthropist.

Designed by Henry Ives Cobb in 1891 for physician and entrepreneur John McGill (an heir to a Canadian-built fur-trading fortune), this Chateauesque mansion has long been a landmark along Drexel Boulevard in Bronzeville. The grand home later went on to become a 34-unit condo development known as McGill Parc.

John C. Cochrane, designer of the Illinois State Capitol building, constructed this house in the Douglas area for lumberman George Wood in 1885. The Queen Anne style mansion was purchased in 1948 by Charles Boyde and Dr. Alva Maxey-Boyd and became a center of culture on the South Side. Maxey-Boyd sold the house to a doctor from New York for $450,000 in 2011.

Architect Edward Burling built the house in 1883 for Samuel Nickerson, founder of the First National Bank of Chicago. Known as the “marble palace” for its ornate stone interior, the property has since been restored and now operates as the Driehaus Museum, conveniently located directly across the street from the Cable House.

This imposing mansion and accompanying coach house occupying a large tree-lined lot along State Parkway was built in 1885 under the supervision of Patrick A. Feehan, the first Archbishop of Chicago. Architect James R. Willett, who served as a Union Army engineer in the American Civil War, designed the ecclesiastical residence with an ornate brick and stone exterior topped with turrets, dormers, and 19 chimneys. The residence hosted famous guests like Franklin D. Roosevelt and Pope John Paul II. Tucked away behind the property, you’ll find one of Chicago’s two surviving woodblock alleyways. Restored in 2011, this type of paving was once common throughout the city, but understandably fell out of favor following the Great Chicago Fire.

Famous Prairie School Architect George Maher designed this house in Washington Park for lumberman Davey Pate in 1901. It stands out for its combination of traditional and contemporary elements. It would later be purchased and occupied by Charles Comiskey of Chicago White Sox fame.

Built in 1870 for prominent businessman, developer, and politician John Raber, this rare pre-fire Italianate house in Englewood was more famous for its vast grounds than the actual building. Its six-acre gardens were once so elaborate and extensive that its original address was on State Street. It has languished for several years and is need of a rehab.

This South Side mansion was built in 1883 by Burnham & Root for Sidney Kent, founder of the Chicago Union Stockyards. It was later home to John "bet-a-million" Gates, who built a fortune in barbed wire and gambled extensively on the stock market. During his time there, it was known as a center of lavish parties for the city's elite. The Kent-Gates House was later converted to apartments and then to condos.

Built in 1902 by Schmidt & Garden for Albert Madlener, son of a prominent liquor distributor, this Gold Coast residence combines elements of the Chicago and Prairie schools of architecture. It was purchased in 1963 by the educational institution the Graham Foundation and hosts art and design-focused exhibits and programming.

This 15,000-square-foot north side house was designed by Prairie School architect Richard E. Schmidt for German brewer Joseph Theurer in 1896. It was bought in 1911 by chewing gum magnate William Wrigley, Jr. The mansion has gone on and off the market in recent years and ultimately sold from foreclosure for $4.65 million—roughly one half of the $9 million figure paid by its previous owner.

This Near South Side house, built for banker Calvin Wheeler in the popular Second Empire style in 1870, is a survivor of the Great Chicago Fire and one of the last still standing along Calumet Avenue. It's second owner, clothier Joseph Kohn, updated it by adding a two-story window bay to the front and the elaborate canopy porch. It was threatened with demolition for a parking lot in 1997 before being purchased and converted to a boutique hotel.

Solon Spencer Beman designed the Near South Side mansion at 1919 S. Prairie Avenue in 1884. Department store magnate Marshall Field—who was living at 1905 S. Prairie Avenue—purchased the property in 1890 for his son, Marshall Field Jr, and hired architect Daniel Burnham to expand the house to an impressive 30,000 square feet. The South Side structure later served time as a psychiatric hospital before it was restored and partitioned into six luxury condominiums in 2007.

Solon Spencer Beman also created this well-preserved home at 1801 S. Prairie Avenue in the Chateauesque style with a limestone exterior adorned with Baroque-inspired ornamentation. Constructed between 1890 and 1892 for wealthy piano manufacturer William Wallace Kimball, the property is currently owned by the U. S. Soccer Federation. The organization uses the former mansion as office space.

This impressive Wicker Park home is one of the largest historic homes that comprise Chicago Beer Baron’s Row landmark district. Built in the 1880s for liquor merchant John Henry Raap, the stately red brick structure features a Second Empire exterior with a mansard roofline and a sizeable turret. The Raap mansion served as a rooming house during the Great Depression and was later converted back into a single-family home that blended the historic architecture and modern luxuries. The property hit the market in 2018 for $6.49 million, reported Crain’s at the time. The home was briefly offered as a $15,000 per month rental before getting yanked off the market.