Stripe Expands Chicago Office to Over 222K SF in River North

River North Sees a Rare Expansion

Bisnow reports that amid a challenging landscape for downtown Chicago offices, Stripe is bucking the trend with a major expansion. Crain’s Chicago Business reports that Stripe will more than double its space, upping its commitment to over 222K SF at 350 N. Orleans St. over the next two years.

This move comes with total office vacancy reaching new highs and leasing activity subdued, particularly from major tech tenants. Stripe’s deal is notable in River North, a neighborhood that has attracted several high-profile tech tenants but has also seen large blocks of space sit empty as companies downsize or reconsider office footprints.

The Details

Stripe first entered 350 N. Orleans St. in 2022 with a lease of approximately 45K SF. The company subsequently doubled its space to roughly 89K SF and extended its lease to 2031 in early 2025 before this latest expansion. The latest agreement takes Stripe’s office footprint to more than 222K SF—an increase of over 130K SF.

The expanded space will be delivered in phases, supporting Stripe’s plans to scale its Chicago workforce. Crain’s notes that Stripe is actively seeking to fill around 80 positions in the city. Ownership of the 1.3M SF office property is unsettled; Blackstone faces foreclosure proceedings after defaulting on a $310M loan, and the asset has been quietly marketed for sale by Eastdil Secured.

Tech Leasing Defies Office Drag

Stripe’s move comes at a time when large tech companies have mostly pulled back on office expansion. Across the broader market, major tenants have been shrinking footprints or leaving older buildings in the Loop, contributing to a downtown office vacancy rate of 26.7% in Q1, per Newmark. Even established tech names have shed space or paused hiring. The leasing market has still produced strong brokerage results, showing that high-value deals continue despite slower overall activity.

In this context, Stripe’s substantial expansion stands out, particularly in a market where most headlines involve subleases and consolidations rather than net growth. Few companies, especially in tech, are placing big new bets on urban office space, making this deal a notable exception.

Why It Matters

The Stripe expansion sends a cautiously optimistic signal for Chicago’s beleaguered central business district. The deal is one of the largest new leases by a tech tenant in recent years at a time when downtown vacancy reached a record 26.7% in Q1, according to Newmark’s latest data. Persistent high vacancy and the specter of distressed assets—like 350 N. Orleans St., which faces ongoing foreclosure proceedings—have cast doubt on the speed of any office market turnaround. Yet Stripe’s move shows that high-growth tech firms still see value in large urban footprints, at least when scaling core teams in centrally located, transit-served properties. Stripe’s need for space is also expected to translate into significant local hiring, potentially supporting wider demand in Class A properties.

For landlords and investors, Stripe’s expansion offers both a reassurance and a warning. Flight-to-quality remains acute: the best-located, amenitized assets can still land major tenants, even as weaker properties struggle. With ownership of 350 N. Orleans St. in flux, the lease’s role as an anchor could improve the building’s attractiveness to potential buyers. However, portfolio-level distress remains common, with Blackstone’s experience illustrating the risks still facing downtown office investors. For Chicago overall, Stripe’s bet suggests at least some appetite remains for big, well-located blocks—so long as the tenant’s growth story supports it.

What’s Next

Stripe’s expansion will be rolled out in stages over the next two years as the company hires for dozens of open roles tied to its Chicago operations. Potential new ownership of 350 N. Orleans St. could influence ongoing investments in the property, especially as Eastdil Secured marketed the building and foreclosure proceedings continue.

Market-watchers will be eyeing whether Stripe’s large lease inspires other tech or growth companies to make similar moves, or if it remains an outlier in an otherwise slow leasing environment. Meanwhile, persistent vacancy and pending loan maturities are likely to keep pressure on landlords citywide for the foreseeable future.