Whether Chicago’s real estate dealmakers got the rebound they wanted in 2025 depends on who you ask.
Luxury residential brokers would say it was one of the best years of their careers, and the city’s biggest brokerage was officially absorbed by an even bigger one from New York.
Yet commercial developers and office landlords are still mostly on the sidelines, with only a select few getting back into the game.
Trophy office towers are roaring again, megaprojects stirred back to life and the Midwest’s multifamily landlords are riding some of the strongest rent growth in the nation — a result of dropoffs in new construction that nonetheless helped stave off lenders.
Still, plenty of players, tenants and banks were rattled by distress, and lawsuits containing allegations of foul play and fraud flew back and forth.
These were Chicago’s juiciest real estate stories of 2025.
Office market shows signs of life
After years of headlines about distress and record vacancies, Chicago’s office sector gained real momentum in 2025 — though only at the top end.
The biggest splash came at Salesforce Tower, where developers Hines and Joseph P. Kennedy Enterprises landed a $610 million refinancing. That deal preceded a string of subleases, including space Salesforce rented to Newmark and private equity firm Wind Point Partners, showing trophy space still draws demand from top-tier tenants.
The Bank of America tower at 110 North Wacker Drive secured a $700 million refinancing led by landlord Oak Hill Advisors, marking the city’s largest commercial mortgage-backed securities office loan since the pandemic. With Bank of America the largest tenant in the building and the tower offering high-end amenities, lenders showed a level of confidence that has grown rare for Chicago office buildings.
In Fulton Market, developers Jeff Shapack, Tim Anderson and their partner Walton Street Capital also defied Chicago’s office market woes with a $247 million refinancing for 167 North Green Street.
But the picture wasn’t uniform. Blackstone extended the $1.3 billion loan on Willis Tower for a sixth time, as valuation swings and tenant downsizing kept pressure on the skyscraper.
Plans for office conversions into residential chugged along. And trades within the sector that did occur extended the streak of extreme losses in value from previous sale prices.
New York-based investors were the big buyers: 601W Cos. bought the building at 525 West Van Buren Street for just $35 million, Mike Kohan paid just $45 million for the skyscraper at 311 South Wacker Drive to mark an 85 percent discount from its last sale, while Namdar Realty Group and Mason Asset Management are working on a deal to snag the tower at 190 South LaSalle Street at a steep loss for the seller, Beacon Capital Partners. Plus, the New York-based Stahl Organization partnered with Hines to buy the Boeing Building for just $22 million.
Meanwhile, Neil Bluhm’s aforementioned Walton Street Capital is having a tough time selling its Magnificent Mile office tower at 401 North Michigan Avenue after drawing initial interest from seriously capitalized buyers.
Megadevelopment momentum
Chicago’s major development sites, some long-stalled, made real progress in 2025.
At Lincoln Yards, new investors emerged to buy undeveloped land off the clearance rack, including JDL and Kayne Anderson. They paid $84 million for land on the north side of the Chicago River from Bank OZK, which seized the property from a venture of the original developer, Sterling Bay and its partner Lone Star Funds.
More recently, John Novak emerged as a buyer for much of the southern Lincoln Yards assemblage. The revived momentum pointed to a more phased, modular approach, replacing the bigger, $6 billion buildout originally pitched by Sterling Bay.
Despite suffering some setbacks, Bally’s pushed ahead on its $1.7 billion permanent casino complex in River West. Construction rose on the riverfront site, and remained on track for opening in late 2026.
Related Midwest and CRG bought the long-dormant former U.S. Steel site on the South Side in partnership with Blue Owl, teeing up a multibillion-dollar quantum computing project on the lakefront as the anchor of a larger redevelopment play.
And at The 78 megasite, Related and billionaire Joe Mansueto’s Chicago Fire FC secured approval to build a privately funded soccer stadium — the site’s first real vertical development.
Meanwhile, stadium plans for the White Sox and Bears remained uncertain. The Sox were left out of stadium planning at The 78, and the Bears floated a move to Indiana after Illinois lawmakers ignored funding requests.
@properties sale to Compass kicks off new consolidation wave
Chicago’s brokerage landscape shifted when Compass acquired @properties Christie’s International Real Estate in a $444 million deal that closed early in the year.
The move gave Compass a dominant foothold in the city and combined its marketing platform with @properties’ agent base and mortgage and title arms. It also set off a wave of local reactions, as competitors recalibrated, and agents speculated about the merger’s effect on the city’s top firm.
Local legacy powerhouse Baird & Warner bought the Chicago-focused brokerage Dream Town Real Estate to bolster its scale.
But by year-end, Compass had agreed to a $1.6 billion all-stock acquisition of Anywhere Real Estate, which owns Coldwell Banker and Century 21 among other brokerage brands. If approved, the merger would give Compass a sprawling umbrella and further consolidate power at the national level, as brokerage industry norms get scrutinized and reconsidered.
South Side multifamily distress
While rents climbed and inventory stayed tight across Class A apartments, the South Side’s multifamily sector struggled with legal, financial and reputational blows.
In South Shore, properties owned by Wisconsin-based investor Trinity Flood were raided by federal immigration agents following a wave of tenant complaints and building code issues. The ownership group had already faced foreclosures and lawsuits due to subpar property conditions and loan payment defaults before the stunning law enforcement operation carried out in the middle of the night.
Nearby, legal fights broke out between once-active investors. Chikoo Patel, who oversaw a portfolio of dozens of buildings across the South Side, was sued by multiple partners, including investor Shai Wolkowicki, who claimed Patel improperly siphoned off millions of dollars for his own use. Wolkowicki and Patel also faced a foreclosure lawsuit from lender Old National Bank. Separately, Wolkowicki also sued Mitch Goltz over claims of mismanagement in their prolific former retail development partnership, GW Properties.
Back on the South Side, New York-based Emerald Empire’s apartment portfolio, which included over $600 million in real estate it purchased in bulk from Pangea Properties in 2022, slid into forbearance on a massive Fannie Mae loan.
Across Chicagoland, The Real Deal also tracked the nearly $100 million that investors who got blacklisted by Fannie Mae tossed into regional real estate.
Lakefront luxury reaches new peaks
High-end housing surged past previous records in 2025, especially along the North Shore and into Wisconsin’s Lake Geneva.
A Winnetka lakefront estate owned by Walton Street Capital executive Jeff Quicksilver and his wife Ashley Quicksilver sold for $32.5 million — the most ever paid for a home in Illinois — just weeks after another mansion in the same wealthy power town traded for $31 million.
The Quicksilvers set another local record as they downsized to a $14.5 million Kenilworth mansion, and a $20 million Lake Geneva sale also closed, reinforcing a strong year for waterfront trophy homes. North Shore specialist Jena Radnay closed both the big Winnetka deals as well as the Kenilworth sale, marking a new peak for her brokerage practice.
But it wasn’t all good news for Lake Michigan’s shoreline homeowners. The residents who sued the Winnetka government for overhauling rules to make it harder to develop blufftop land along the water suffered a setback in court. Yet they’re still fighting to repeal the regulations.
Lake Geneva also saw litigation. The historic Aloha Lodge became the subject of a lawsuit after an initial buyer walked away from a $37.5 million contract. But demand overall stayed strong, with multiple bidders vying for move-in-ready estates at about the $10 million range. Interest rate pressure didn’t seem to reach this end of the market.
Property tax troubles plague all of Cook County
It’s a perennial theme in Chicago real estate: property tax chaos.
Delayed bills left buyers in limbo and cost Chicago Public Schools nearly $250,000 a day in interest on short-term loans it took on to cover the gap from late property tax revenue. Assessments across the South and West Sides jumped, with some homeowners discovering tax bills that had doubled.
Late in the year, a federal court ruled the county’s annual delinquent tax sale system unconstitutional, casting uncertainty over how liens would be handled moving forward.
The result of it all was deal slowdowns, broken underwriting assumptions and increased tension between commercial landlords and homeowners. With no sure fix in place, tax policy remains a key concern heading into 2026.
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