Digging into Chicago’s Biggest Brokers and Builders

Chicago’s top dealmakers of the South Side and the way they do business are explored in The Real Deal’s March issue.

Compass’ Nadine Ferrata, known as the “Queen of the South Loop,” came out on top of a TRD Data ranking of residential brokers limited to 43 neighborhoods on the South Side of the city, and there were several other real estate royals dominating high-end lakefront locales like Bronzeville and Hyde Park, to working-class areas further inland.

On the development side, TRD Data also put together the Hard Hat Hierarchy: a ranking of top contractors by dollar volume of the projects they’ve won in Chicago over the past year. Clark Construction Group ended up in first place, while the industry rebounded in 2024 from a brutal drop in business the year before. But with construction costs that were already rising even before President Trump’s plans for tariffs took effect, there’s even more uncertainty ahead now for these firms.

For TRD’s The Closing, landlord Albert Friedman, the transformative force behind River North’s rise as an economic engine, breaks down his origins, retail tactics and thoughts on how to fix Chicago’s struggling office market.

In Chicago’s suburbs, developer Mark Meyer’s firm E&M Strategic is facing a muddy foreclosure of a $24 million construction loan for a stalled Skokie hotel project that took in public funding and also faces allegations from contractors who say they’ve gone unpaid for their work. Other hotel news includes struggling hospitality firm Sonder bailing on a lease of a River North hotel as its landlord sues for $4 million.

Longtime CRE player Zaya Younan is fighting against his lender Royal Business Bank’s multi-pronged foreclosure that threatens to strip the landlord of a struggling Arlington Heights office and his luxury home outside Los Angeles. The legal back-and-forth includes some odd arguments.

Chicago’s multifamily market raked in a $160 million CMBS refinancing for the 481-unit 540 North State Street. It was a mixed signal, as the deal both shows a level of confidence in the city’s big apartment assets while also requiring the under-the-radar landlord to cover a $16 million debt gap to retire a previous loan taken out when the building notched a higher appraisal a decade ago.

Finally, the office leasing market got a couple jolts as landlords work to bounce back from the pandemic-induced downturn. Fintech firm Stripe doubled its office footprint at the distressed 350 North Orleans Street tower to around 89,000 square feet, investment firm Blue Owl is taking another floor at 150 North Riverside Plaza, and law firm Goldman Ismail Tomaselli Brennan & Baum is set to nearly double the size of its lease in a relocation from 200 South Wacker Drive to 191 North Wacker.