Hines is in early talks to buy Boeing’s former Chicago headquarters at 100 N. Riverside Plaza, according to people familiar with the matter. The 36‑story riverfront tower in the West Loop has been a repeat looker this year as would‑be buyers test whether a major repositioning can pencil out. The conversations are early, and they could fizzle if financing or tenant plans don’t come together.
CoStar reports Hines is negotiating to acquire the building from Boeing, while also noting that the weak office market and high borrowing costs could derail a deal. The outlet adds that an earlier agreement with another buyer recently collapsed — a reminder that in this market, nothing’s done until it’s done.
Sterling Bay’s July Overture And Pricing Pressure
Chicago developer Sterling Bay emerged as a high‑profile suitor over the summer, with local outlets tracking talks in July. Coverage in The Real Deal placed that interest in the context of broader financial strain that’s made many buyers cautious about big office bets.
Boeing announced in 2022 that it would shift its corporate headquarters to the Washington, D.C., region while keeping a Chicago presence, and contemporaneous reporting indicated it planned to maintain West Loop offices. CBS Chicago said the company had roughly 400 Chicago employees at the time of the move and intended to keep a significant local footprint.
Leasehold Maze Complicates Any Deal
One big wrinkle: Boeing is selling only the building’s leasehold, while the land underneath is owned separately — a setup that can make financing and any makeover trickier. According to CoStar, the Stahl Organization controls the site via a 99‑year ground lease running to 2084, and refinanced that interest in 2021 with about a $40 million loan maturing in 2031. CoStar also outlines potential buyer playbooks — teaming with the landowner or negotiating a buyout to consolidate ownership — and cites recent Cook County filings showing Boeing signed a memorandum of lease for floors 27–29, with the recorded office lease running from September 2026 through August 2032 and including extension options.
Then there’s the market itself. Leasing demand is still well below pre‑pandemic norms, and debt is pricier, which squeezes returns on buildings that need upgrades or tenant rehabs. Bisnow and others have chronicled buyers hunting for deep discounts while lenders and equity partners keep their powder dry.
What To Watch
If Hines pushes ahead, it could try to partner with the landowner or pursue a ground‑lease buyout to streamline ownership — both heavy lifts that require time and capital. Tenant moves at 100 N. Riverside — whether Here Technologies and others trim, expand, or sublease — will be central to whether any financing can click.
For now, it’s quiet on all sides. The most telling near‑term signals will be fresh Cook County filings or public statements from Hines, Boeing, or the Stahl Organization. We’ll be watching those records — and the local rumor mill — for anything concrete.
