Another glass-and-steel relic of Chicago’s downtown office boom is heading to the sale block.
Toronto-based Manulife hired JLL to sell the 40-story office tower at 55 West Monroe Street, an 815,074-square-foot building in the heart of the Loop that is more than 80 percent vacant. CoStar reported that marketing materials show brokers Jaime Fink, Bruce Miller and Sam DiFrancesca are pitching the tower as both a leasing opportunity as well as a conversion candidate for uses other than office space.
Designed by late architect Helmut Jahn, the 46-year-old tower is expected to trade for far less than replacement cost — or how much it would cost to build today — a reality that could give a buyer room to pump capital into new office leases or carve up large swaths into apartments, hotel rooms or a hybrid of both, according to the outlet. JLL’s brochure floats scenarios including up to 532 hotel keys or 296 apartments.
The listing lands as Chicago pushes to remake parts of its central business district. Several LaSalle Street properties are already being partially converted to affordable housing under a city-backed incentive program aimed at tackling stubborn vacancies and reviving foot traffic.
Manulife has been here before. The firm quietly explored a sale of the building at 55 West Monroe Street in 2022, but failed to secure a buyer. If it closes this time, it would mark the insurer’s second major Loop office exit at a sharp discount in just over a year, according to the publication.
In early 2025, Manulife sold the 41-story tower at 200 South Wacker Drive for $68 million — a fraction of the $214.5 million it paid in 2013 and well below the roughly $151 million loan tied to the property. The buyers, Glenstar and a Minnesota investor, have since launched a $30 million renovation to stabilize leasing.
Manulife paid $243.3 million for the building at 55 West Monroe Street in 2014, according to CoStar and Cook County records, and notably did not place debt on it. — Eric Weilbacher
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