These Were Chicago’s Juiciest Real Estate Stories of 2024

Tales of lawsuits accusing bigtime developers of fraud, South Side landlords who were convicted of federal crimes and some of the biggest names in real estate getting rocked by financial distress shaped Chicago’s news cycle this year.

There’s never a shortage of shocking, sly and smart business moves — along with constantly dizzying political drama — within the Windy City’s real estate market. This year was especially juicy, as high-end homeowners took haircuts (including one from the governor), industry lobbyists parried perplexing taxes and laws, megadevelopment plans shifted and stalled, and foreclosures were filed.

Plus, you might have heard the city’s largest residential real estate brokerage, the Chicago-born @Properties Christie’s International Real Estate that was built into a local powerhouse, was bought for $444 million by its former fiercest rival, Compass.

Here’s Chicago’s spiciest real estate deals and developments that drove the market this year — and how they might continue to make an impact in 2025.

Luxury letdowns

Several super high-end sales took place this year in Chicagoland’s housing market, including a Lincoln Park mansion that was the priciest single-family home ever sold in the city, Ken Griffin’s $19 million two-floor penthouse in a condo tower, bought by his political nemesis Gov. J.B. Pritzker. And Michael Jordan’s suburban Highland Park mansion sold after 12 years on the market.

One thing they all had in common was the substantial financial losses the sellers took on the deals.

The Lincoln Park mansion on North Burling Street that sold for $15 million cost sellers Richard and Michaela Parrillo $65 million to build. Griffin bought the two floors of raw space within the 9 West Walton Street tower for $34 million in 2017. And Jordan once wanted nearly $30 million for his highly customized mansion in Highland Park before making a series of cuts to his listing price over the decade-plus it was on the market.

What’s driving the downturn?

Demand for downtown condos is in the doldrums, as remote work patterns and perceptions of crime in Chicago persist. The St. Regis Chicago’s developer Magellan made a $117 million bulk sale of a batch of more than 80 units in the 101-story skyscraper that failed to draw buyers to Denver-based GD Holdings, which also bought the hotel portion of the tower last year.

This year marked the first in recent memory without a major downtown Chicago condo project under construction, though Sulo Development filed plans that could end the cold streak with a proposal to build three towers with more than 240 condos in Fulton Market.

Yet there’s still plenty of optimism in the ultra-luxury market in Chicagoland. A string of North Shore sellers this year listed an unusually high number of lakefront mansions for more than $10 million, a pricepoint rarely crossed in the region. The Winnetka estate of a retired Goldman Sachs executive asking $35 million is the largest listing heading into 2025. That suburb remains at the top of the market, exemplified by billionaire Justin Ishbia’s ongoing construction of a mansion set to cost $77 million.

Political clashes

Even with Winnetka’s peak status, it was the center of prickly political drama tied to real estate.

Homeowners in the village sued the local government for passing laws aimed at limiting development along the lakefront, claiming it drained their properties of perhaps “hundreds of millions of dollars” in cumulative value. The rules were advanced as a backlash against Ishbia’s controversial mega-mansion plan receiving approval without much scrutiny.

The lawsuit remains pending in federal court and is one of several local government fights in which the real estate industry played an integral role this year.

In Chicago, voters turned down a transfer tax hike on property sales of $1 million or more that was supported by Mayor Brandon Johnson. The election ended a complex dispute between the commercial real estate lobby and the tax’s progressive supporters that drew conflicting legal opinions and led to an Illinois Supreme Court decision.

With the transfer tax’s defeat at the ballot box, Johnson in recent weeks was forced to look for other revenues to plug a big budget gap the city faced in 2025. He initially proposed a $300 million property tax hike. That drew vehement backlash from the commercial real estate industry as well as aldermen, who unanimously voted it down.

Meanwhile, Chicago went through its triennial property-tax reassessment, with commercial landlords — and especially downtown hoteliers — once again complaining that Assessor Fritz Kaegi is overestimating the values of large properties, thus driving up their tax bills and hurting their market pricing.

Furthermore, multifamily landlords in Northwest Side neighborhoods and Pilsen panicked over an ordinance passed by the Chicago City Council this fall that could have stalled building sales. The city initially gave tenants in certain gentrifying neighborhoods the right of first refusal to buy their own buildings when the landlord moves to sell, and renters initially weren’t required to have proof of funds to make such purchases, potentially giving them the option to drag out deals for months.

Outcry from industry players led the city to water down the ordinance so any tenants who are serious about buying their own building now have to show they have financing to close deals. Although landlords are still unhappy with the rest of the rules, which also include substantial hikes for demolition fees among other restrictions meant to slow the depletion of local affordable housing.

Finally, don’t forget this year’s absolutely cutthroat, multi-pronged political showdown in south suburban Dolton centered on self-proclaimed “Super Mayor” Tiffany Henyard, which has drawn FBI attention amid complaints of mishandled village finances and involves an eviction lawsuit against Henyard, set for a January hearing.

Megadevelopments meet stadium mania

The reason Jerry Reinsdorf and his affiliates have bought $44 million worth of real estate around the United Center came to light this year. The Bulls owner along with the Wirtz family that owns the Chicago Blackhawks revealed a $7 billion plan to redevelop the surroundings of the United Center on the Near West Side.

Real estate players are jazzed by the potential transformation and westward expansion of major commercial real estate development, on the tail of Fulton Market’s success.

The emergence of the so-called 1901 Project — named for the address of the arena at 1901 West Madison Street — was big news among Chicago’s handful of multi-phase, yearslong megadevelopment plans.

Related Midwest is at the center of two of them. It’s the developer working on the real estate aspects of Silicon Valley startup PsiQuantum’s multi-billion dollar plan to bring a quantum computing campus to the 440-acre former U.S. Steel South Works site. Pritzker has promised to pour $500 million of state resources into developing the quantum park, a project set to be neighbored by a $300 million Advocate Health Care hospital development, with which Related Midwest is also assisting.

The massive project sailed through the city approval process this year and has raised hopes for drawing further investment to the South Side.

It has by far the most momentum of any of the other megadevelopments in Chicago, though it’s in its earliest stages. Progress has stalled at some others.

Related Midwest’s other big South Side vision, The 78, on a 62-acre plot between the South Loop and Chinatown, went through a shakeup. The University of Illinois ceased the preliminary construction work on its $285 million research facility that had been set to anchor the south end of The 78, in order to prioritize putting university resources into the quantum facility.

Alternatively, the Reinsdorf-owned Chicago White Sox started talks with Related Midwest on building a baseball stadium on The 78, but they haven’t gotten much help from lawmakers securing the taxpayer-funded subsidies they claim are needed to propel such a project. Ditto for the NFL’s Chicago Bears in the team’s pursuit of a new lakefront stadium. Joe Mansueto’s Major League Soccer team, the Chicago Fire, is also eyeing building a soccer-specific stadium at The 78.

On the North Side, Sterling Bay’s Lincoln Yards was also considered by the Fire, but the site — still vacant aside from an empty life sciences facility — isn’t considered the frontrunner. Lender Bank OZK wrote down $21 million of the $128 million in debt secured by Lincoln Yards, with the financier saying it was growing “impatient” with Sterling Bay’s progress.

Sterling Bay has been hunting for investors to inject additional capital into the megaproject to help kickstart it, with the real estate arm of private equity giant Kayne Anderson this year considering a deal, but one hasn’t moved forward.

Development firm Farpoint, led by Scott Goodman, is also in play for the Bears with Farpoint’s multi-billion pursuit of its Bronzeville Lakefront project, which involves the redevelopment of the former Michael Reese hospital site. The football team reportedly reevaluated the property for a stadium. The developer and its partners have shifted their priority to bringing residential and senior housing with retail to the site first, with later plans to build a health innovation hub led by Israel’s Sheba Medical Center.

Foreclosure fever

Not even the most reputable firms in commercial real estate were safe from the financial distress wrought by lending markets with elevated interest rates and a lack of demand from office tenants in the wake of the pandemic.

AmTrust RE and Beacon Capital Partners were among those with previously solid track records that were hit with nine-figure foreclosure lawsuits for Chicago office towers this year.

Multifamily didn’t prove to be a safe harbor, either. JP Morgan Investment Management took steep losses on the sales of Chicago apartment towers, and several other landlords in the sector are facing massive foreclosure suits, as well. Chicago-based multifamily development specialist CA Ventures is going through especially hemorrhagic bleeding.

The good news for the market is that sales — mostly out of distress and at major discounts from previous values — started to close at a larger volume this year, establishing a market bottom.

Discount hunters in the office market such as Minnesota-based investor Patrick Halloran and Florida-based Alfred Teo picked up distressed buildings in the suburbs, and Halloran is working on an acquisition in the city. Beacon got in on the buy side, too, putting up $125 million for 333 West Wacker Drive to close Chicago’s largest office purchase in two years.

Buyers are betting the deep discounts will help them afford the expensive costs of leasing commissions, building renovations and incentives for tenants to refill office buildings and drive their values upward.

However, whether office building values ever reach their pre-pandemic peaks in the age of hybrid work arrangements and perpetual battles over Chicago property taxes remains to be seen.