Chicago, a city renowned for its architectural marvels and vibrant neighborhoods, is also a playground for some of the world’s wealthiest individuals. From historic mansions to ultra-modern penthouses, Chicago’s billionaires have a clear penchant for luxury living. Let’s explore the exclusive neighborhoods, landmark buildings, and record-breaking sales that define the city’s elite real estate landscape.

Chicago Neighborhoods the Ultra-Wealthy Call Home

Several key neighborhoods attract the city’s richest residents, each offering a unique blend of luxury and lifestyle.

Lincoln Park is a perennial favorite among Chicago’s elite, known for its lush, tree-lined streets and close proximity to the lakefront. Notable residents include Morningstar CEO Joe Mansueto, who constructed a $22 million mansion spanning seven lots, and Penny Pritzker, whose $7 million home is one of the largest in the area. The neighborhood’s real estate prestige was further solidified in 2024 when a mansion on Burling Street sold for a record $15.25 million.

The Gold Coast is historically synonymous with opulence, featuring grand mansions and exclusive luxury condos. Billionaire Ken Griffin once owned a $15 million condo in the esteemed Park Tower. The most expensive sale in this neighborhood was a penthouse at 4 East Elm, which fetched $10.125 million in 2025.

Streeterville is home to some of the city’s most iconic residential high-rises, including the Park Tower and the St. Regis Tower. It’s here that George Lucas and Mellody Hobson are combining two units in the Park Tower to create a staggering $33.5 million duplex penthouse, set to become the most expensive condo in Chicago’s history.

Meanwhile, River North attracts billionaires seeking a more modern, cosmopolitan lifestyle with its vibrant art scene and sleek luxury high-rises. A unit in the One Chicago building set a neighborhood record, selling for $5.6 million.

Landmark Luxury Condo Buildings in Chicago

Several buildings have become magnets for Chicago’s billionaire class, each offering a unique brand of opulence.

• The St. Regis Tower (363 E Wacker): A prime example of high-rise luxury, this Streeterville tower recently saw a unit sell for a staggering $20.56 million to Mexican billionaire Germán Larrea, one of the highest sales in the city’s history. Other units here regularly close in the $7.5 million–$8.6 million range.
• Park Tower (800 N Michigan): Another Streeterville favorite, this building recently saw an 8,500 sq ft penthouse sell for $11.7 million.
• One Chicago (14 W Superior): In the trendy River North neighborhood, this modern high-rise set a new benchmark with a penthouse selling for $8.9 million.

Other notable sales in the city’s most exclusive neighborhoods include a penthouse at 9 W Walton in the Gold Coast selling for over $5.5 million and a massive 9,000 sq ft unit at 65 E. Goethe St. closing for $9.3 million in 2024.

Suburban Retreats and Record-Breaking Sales

While many billionaires prefer urban luxury, others opt for the tranquility and space of the suburbs. Areas like Kenilworth and Winnetka are home to sprawling estates and stunning waterfront properties. Most notably, billionaire Justin Ishbia is currently constructing a massive mega-mansion on Sheridan Road in Winnetka. The ambitious project involved consolidating several lakefront lots, with land acquisition and construction costs reportedly totaling over $77 million.