One of the Loop’s most recognizable office towers is quietly up for grabs, and it might not stay an office for long. Manulife has put its 40-story Helmut Jahn-designed high-rise at 55 West Monroe on the market, hiring JLL to hunt for a buyer and pitching the building as either a straight office lease-up play or a candidate for a full-blown conversion into apartments or hotel rooms. The roughly 815,000-square-foot tower is now more than 80 percent vacant, turning it into one of downtown Chicago’s most visible test cases in the conversion wave rolling through the Loop.
What brokers are pitching
JLL’s marketing materials peg the tower at 815,074 rentable square feet and show it is about 19.3 percent leased, which leaves roughly 657,000 square feet available for a new owner to reposition, according to JLL. The pitch highlights what brokers call “significant repositioning optionality,” with large, contiguous blocks of vacancy that make either a major conversion or a value-add lease-up more realistic than in a partially full building. JLL’s online deal room for the property was last updated on February 24, 2026, indicating the offering is very much live.
Conversion scenarios on the table
Marketing concepts floated to investors sketch out several futures for the tower, from heavier hotel uses to residential layouts. Depending on how the floors are carved up, the building could accommodate as many as 532 hotel keys or roughly 296 apartments, as reported by The Real Deal. That kind of range shows how owners are now forced to underwrite older office towers: buyers are weighing the cost to retrofit against replacement-cost economics and a slow but steady appetite for downtown housing and hospitality.
Manulife's Loop track record
The listing is the latest step in Manulife’s ongoing reshuffle of its Loop portfolio. A Manulife affiliate bought 55 West Monroe in 2014 for about $243.3 million and did not put debt on the building, according to CoStar. In early 2025 the company also unloaded the 41-story tower at 200 South Wacker Drive for roughly $68 million, a sharp discount from earlier valuations, and the new owners have since launched about $30 million in renovations aimed at shoring up leasing there.
Why the Loop matters
The decision to formally shop 55 West Monroe comes as the city and a roster of developers experiment with different conversion paths to revive the Loop’s core, including partial affordable housing overlays on LaSalle Street that are intended to boost pedestrian traffic and daytime population in the traditional financial district. As outlined by The Real Deal, properties that trade below replacement cost give buyers breathing room to either fund aggressive leasing campaigns or pay for deeper gut rehabs that support entirely new uses. How an eventual buyer chooses to spend into that pricing gap will determine whether this block leans back into office life or flips its identity to residents and hotel guests.
Who’s running the sale and what to watch
JLL brokers Jaime Fink, Bruce Miller and Sam DiFrancesca are listed as the sale team, and they are expected to court both traditional office investors and conversion-first buyers, according to JLL. Market watchers will be looking not just for an initial round of bids or a preferred-use study, but for a more decisive signal if a buyer ultimately files plans to convert large stacks of floors. That type of move would trigger a fresh set of zoning, financing and timing decisions and could reset expectations for how other aging Loop towers are valued.
Whatever path the next owner chooses, 55 West Monroe is positioned to be an early bellwether in 2026 for how big, older, largely empty Loop towers get priced and repurposed. In the months ahead, leasing chatter, planning filings or a buyer announcement should reveal whether this Helmut Jahn high-rise tries to stage an office comeback or trades in its cubicles for kitchens and keycards.
