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Report: Chicago’s famous diamond-shaped skyscraper is for sale

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The 661,500-square-foot Loop office tower could fetch $132 million

Flickr Creative Commons/Howard Lifshitz

Chicago’s iconic Crain Communications building at 150 N. Michigan Avenue—a fixture on the Windy City skyline for 33 years—could soon change hands in a deal reportedly worth $132 million. According to Crain’s Chicago Real Estate reporter Alby Gallun, building owner Manulife has hired brokerage firm HFF to market the commercial property. The Toronto-based insurance company acquired the 41-story tower in 2012 for $102 million and has invested more than $18 million in upgrades and amenities such as bike parking, a conference center, and tenant lounge.

Designed by local architecture firm A. Epstein and Sons (now Epstein Global) in 1984, the high-rise is clad in alternating horizontal bands of aluminum, stainless steel, and silver reflective glass. Designed to maximize views of Lake Michigan and Grant Park, the upper portion of the building features a dramatic, 45-degree sloped face that is often illuminated to spell out messages such as “Go Cubs.” It is perhaps best recognized for its prominent role in the 1987 film Adventures in Babysitting.

Known by a number of nicknames inspired by its diamond crown or debatable likeness to human anatomy, the tower was formerly dubbed the Associates Center when it first opened. The skyscraper went by the official names of the Stone Container Building and the Smurfit-Stone Building before its most recent rechristening as the Crain Communications Building five years ago.

The building is currently about three-quarters leased and could be a lucrative, if not risky, opportunity for a buyer looking to raise the property’s worth. The Crain’s article suggests this could be done by filling up the building with tenants and/or increasing rents before flipping the tower for more cash.

According to HFF’s marketing flyer, 150 N. Michigan Avenue “checks all the boxes for an excellent value-add investment, including current vacancy, attractive basis, appeal to creative users and technology tenants, (and) an extremely favorable financing environment, as well as a realistic and readily achievable exit strategy.”