The most important thing to remember when shopping here is lLocation, location, hang gliding Credit: Midwest Real Estate Data

In 1952, the New Yorker ran the three-part profile of Chicago that gifted us with the epithet the “Second City.” A sprawl of blue-collar workers and “suburban-looking people,” Writer A.J. Liebling charged the “not-quite metropolis” with overstating its status as a world-class city—a term Liebling reserved for New York. Since then, the city of broad shoulders has had a complicated relationship with luxury goods.

For some, Chicago will always be a city of rolled-up sleeves. The sign that hung over Michigan Avenue during Liebling’s visit feels immodest today: This is the Magnificent Mile. It is lined with the most beautiful buildings and the finest and most luxurious shops in the World. But for others, the days of Carl Sandburg’s “stormy, husky, brawling, / City of the Big Shoulders” are over.

The city’s priciest-ever property listing was posted earlier this week by luxury real estate broker Chezi Rafaeli. For $32,000,000, you can own the 89th-floor penthouse suite of the Trump International Hotel & Tower. With seven bedrooms and 14,260 square feet, 360-degree views, five fireplaces, a theater—and, as of yet, unfinished floors and no doors—the penthouse is something of a high-end “fixer-upper.”

“There are a lot of people who have been looking at it,” said Rafaeli in a phone interview. Though interested parties normally visit with a team of contractors, the broker is confident that someone will pick up the check to turn this lofty glass expanse into a home.

“The people that can afford to buy this kind of property, chances are, they’re willing to spend a lot of money to customize it to their lifestyle,” Rafaeli added. For a bit of context, Michael Jordan’s 56,000-square-foot Highland Park home only came in at $29,000,000.

Asked how the penthouse compares to similar units in New York that are being rented rather than sold, to attract those wary of grand investments, Rafaeli responds, “It’s a different market than in New York.”

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