AmTrust pays $77M for Chicago apartment tower, as Cortland takes loss

AmTrust’s $77 million message to the Chicago market is that it’s all-in on apartments, even as its massive office bets go south.

The New York-based firm is expanding its Windy City multifamily focus with the acquisition of the 25-story tower at 220 West Illinois Street — at a big discount, according to public records. The deal marks a brutal exit for Atlanta-based seller Cortland, which paid $105 million to buy the 188-unit building in mid-2022, as part of a purchase of a larger national portfolio from Singapore-based Mapletree, records show.

The $77 million price marks a nearly 27 percent valuation haircut in less than four years — a jarring loss in a submarket where operational performance is actually hitting record highs. The new value is also well below the $91 million Mapletree paid to buy it in 2019, records show, right before the pandemic drilled downtown commercial building appraisals.

The sale to AmTrust highlights the bizarre decoupling currently defining the Windy City. Downtown apartment rents surged by more than 8 percent in 2025, as the construction pipeline effectively evaporated, according to Chicago-based Integra Realty Resources. With the city facing its thinnest completion schedule in decades, landlords have unprecedented leverage with tenants.

Yet for Cortland, record rents weren’t enough to outrun the interest rate meat grinder. The $28 million loss on the building at 220 West Illinois proves that even “Class A” status can’t protect a balance sheet from cap rate expansion and rising Cook County property taxes. Still, AmTrust’s purchase price was more than enough to cover the balance of a $47 million loan Cortland took out on the property last year from BMO Bank, property records show.

For AmTrust, the acquisition is the second leg of a strategic pivot. It follows the firm’s $88 million purchase of the 213-unit Parkline Chicago multifamily building at 60 East Randolph Street in September 2024. By securing over 400 high-end units in prime locations over the last 18 months, AmTrust is betting Chicago rental demand is a safer harbor than the volatile office sector.

Cortland didn’t immediately return a request for comment, while AmTrust RE President Jonathan Bennett wasn’t immediately available Monday morning, according to a spokesperson.

Office holdings in distress

The move into apartments comes at a critical time for AmTrust, as some of its prominent Chicago office investments circle the drain. Nowhere is this more evident than at Illinois Center, the two-tower, 2.1 million-square-foot office complex in the East Loop.

The property is a portrait of downtown office distress. After special servicer LNR Partners filed to foreclose on a $260 million securitized loan in late 2024, a receiver, Trigild IVL, was appointed to oversee the property’s management in February, officially stripping control from AmTrust, according to a loan report.

Once a bustling hub, occupancy at the towers cratered to just 48 percent at the end of 2025, while total revenue for the complex fell to $32 million last year, a steep drop from $47.2 million in 2024 and less than half of the $72.9 million generated in 2023, according to loan data. Illinois Center, underwritten at a $390 million valuation in 2015, saw its appraisal slashed to just $85.7 million in June 2024, the loan data shows.

AmTrust also owns the 25-story office property at 33 North Dearborn, and the distressed office property at 135 South LaSalle Street, a largely vacant building slated for conversion into 386 apartments for $241 million, backed by nearly $100 million in public subsidies.

While LNR advances foreclosure proceedings on its Illinois Center towers, AmTrust has kept RPM Living as the property manager for its latest apartments at 220 West Illinois.

At a cost basis of about $410,000 per unit at that tower, AmTrust is buying into a record-high rent environment at a steep discount compared to the previous cycle’s peak.