On June 10, the Chicagoland Chamber of Commerce convened leaders across technology, real estate, and finance for Chicago at a Crossroads: Rebuilding the Core, part of the Chamber’s signature civic dialogue series focused on the forces shaping the city’s economic future.
Held at the University Club of Chicago and moderated by Tim Burke, President and COO of Old National Bancorp, this installment centered on a defining question: how major investments from companies like Google and JPMorganChase, alongside evolving market dynamics, are reshaping downtown and signaling what comes next for Chicago’s core. Featuring Winton Steward (Google), Kyle Kamin (CBRE), and Anthony Maggiore (JPMorganChase), the conversation underscored both the urgency and opportunity of this moment.
Kyle Kamin framed the moment bluntly: “This wasn’t just a normal cycle. There are all sorts of signals that suggest we are at a turning point.” While acknowledging ongoing challenges like office vacancy and limited new construction, he pointed to rising job growth and declining retail vacancies as evidence of real momentum. His takeaway was clear. The fundamentals are strengthening, but Chicago must do a better job telling that story to the market.
For Winton Steward, major corporate investments are already signaling a shift in expectations. “The Thompson Center is the next chapter for Google in the city and the state. We believe that high-level working teams want more than just offices, they want hubs that are vibrant, open to the public, and conducive to collaboration.” His comments reinforced a broader theme that downtown’s future will be defined less by isolated office towers and more by integrated, amenity-rich environments anchored by transit and public-facing space.
Anthony Maggiore grounded JPMorganChase’s decision to modernize Chase Tower in long-term institutional commitment. “JPMorganChase’s reason for choosing to grow in Chicago has been anchored on three attributes, which are our legacy, our people, and our corporate vision for responsibility.” He emphasized that reinvestment was not just about real estate, but about culture, retention, and creating an ecosystem that supports how employees live and work. Across the discussion, he returned to the idea that attracting talent now depends on the full environment around the workplace, not just the building itself.
Talent, in fact, emerged as the city’s strongest competitive advantage. “It’s all about talent and always has been in Chicago,” Kamin noted, pointing to the depth and diversity of the labor pool as the key driver behind corporate and investor confidence. At the same time, he highlighted an emerging risk: infrastructure, particularly digital capacity, must keep pace. “Every big institution is invested in data center growth, so to maintain that competitive advantage we need to continue to invest in our grid.”
Looking beyond physical development, Steward defined what corporate staying power requires today. “If it’s artists, if it’s sustainability efforts, if it’s education efforts, if it’s small business support, we want to be in all those spaces.” His comments underscored that large employers are increasingly expected to contribute to broader civic outcomes, not just economic ones.
The conversation also reinforced that housing, connectivity, and public realm investments are inseparable from economic growth. Panelists pointed to the need for a balanced mix of residential development, affordability, and transit access to sustain Chicago’s talent pipeline and ensure long-term competitiveness.
Looking ahead, the panel aligned on what success would look like a decade from now. Maggiore emphasized execution and coordinated planning across commercial and residential growth. Steward pointed to projects like the Thompson Center creating vibrant, shared spaces. Kamin stressed the importance of transit investment to expand access to opportunity. Moderator Tim Burke closed on a unifying note, highlighting the need for accountability and collaboration to turn these investments into lasting impact.
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