A local office landlord and a high-net-worth investor from Minnesota are teaming up on their third big Chicago office acquisition since late 2024, agreeing to pay more than $100 million for a 46-story office tower in the Loop business district.
Chicago-based Glenstar and Minnesota-based investment partner Patrick Halloran have a deal to buy the 966,000-square-foot tower at 500 W. Monroe St., according to people familiar with the situation.
The exact price could not be determined, but it is believed to be between $100 million and $110 million.
That is a significant discount to the value of a $270 million loan on the property that current owner Spear Street Capital failed to pay off when it matured in January 2025.
Late last year, lender JPMorgan Chase hired JLL brokers to sell the loan, with the buyer expected to then take possession through a deed in lieu of foreclosure, a form of voluntary surrender.
Glenstar’s deal is not completed and still could fall apart amid a continued challenging market for office sales throughout the country.
If the deal is finalized as expected, it would be the third acquisition by Glenstar and Halloran since October 2024, when they first teamed up to buy the two-tower Presidents Plaza near O’Hare International Airport for $62.1 million. Last year, Glenstar announced plans to spend $16 million on move-in-ready suites and set aside an undisclosed sum to fund new leases.
In January 2025, Halloran again teamed up with Glenstar to buy the 40-story office tower at 200 S. Wacker Drive along the Chicago River in the Loop for $68 million. They recently announced plans to spend about $30 million on upgrades, including converting the lower five floors into new amenities.
The playbook at 500 W. Monroe is expected to look similar, with the partners buying a tower at a massive discount to its previous valuation — San Francisco-based Spear Street bought it for $412 million in October 2019 — and investing on upgrades to fill large blocks of space that are already vacant or expected to be available soon.
At the time 500 W. Monroe went on the market for sale, the property was 75.4% leased with a weighted average lease term of 4.7 years.
The Glenstar-Halloran partnership and JPMorgan Chase did not immediately respond to requests for comment from CoStar News. Spear Street declined to comment.
Halloran and Glenstar are among the investors lining up multiple Chicago office acquisitions at historically low prices, betting on a long-term recovery of leasing and property values.
Kohan Retail Investment Group recently struck a deal to buy Citadel’s former headquarters, a 37-story tower at 131 S. Dearborn St., CoStar News first reported in February.
That follows previous deals by the Great Neck, New York-based firm for the 65-story building at 311 S. Wacker Drive and the 28-story building at 33 W. Monroe St.
For the record
The seller is represented by JLL brokers Tom Hall, Bruce Miller, Jaime Fink and Sam DiFrancesca.