The Chicago at a Crossroads series is one of the Chicagoland Chamber of Commerce’s premier forums for exploring the issues shaping our region’s future. Presented by Old National Bank, the program brings together business leaders, policymakers, industry experts, and civic stakeholders for candid conversations about the opportunities and challenges facing Chicago’s economy. From emerging technologies and workforce development to downtown revitalization and economic competitiveness, Chicago at a Crossroads creates space for the ideas and partnerships that help move our region forward.
Over the past year, the series has continued to attract influential voices and timely discussions. In March 2026, Chicago at a Crossroads: Cementing Chicago’s AI Advantage examined how businesses and institutions can leverage artificial intelligence to drive innovation, strengthen competitiveness, and prepare the workforce for the future. The conversation featured leaders from United Airlines, Amazon Web Services, and the broader technology community, highlighting Chicago’s growing position as a national hub for AI and advanced technologies.
In June, the Chamber convened Rebuilding the Core: Catalytic Projects Reshaping the Heart of Chicago, bringing together executives from Google, JPMorganChase, and CBRE to discuss the major investments transforming downtown Chicago. The discussion explored how public and private sector leaders are reimagining the city’s core through projects such as the Thompson Center redevelopment, Chase Tower renovation, and other transformational investments that will influence Chicago’s economic future for years to come.
The series also spotlighted the role of higher education in regional growth with Universities as Economic Engines: Tapping the Power of Research & Talent. Leaders from the University of Illinois Chicago, the State of Illinois, John Deere, and the University of Illinois Research Park explored how research institutions, academic-industry partnerships, and talent development can accelerate innovation and strengthen Chicago’s competitiveness.
These recent events are part of a broader tradition of thought leadership that has made Chicago at a Crossroads a trusted platform for meaningful dialogue. Throughout the series, conversations have examined issues ranging from economic development and technology adoption to public policy, workforce preparedness, infrastructure, innovation, and the long-term growth of the Chicagoland region. Each program is designed to move beyond headlines and offer practical insights from the leaders helping shape Chicago’s future.
None of this would be possible without the continued partnership of Old National Bank, presenting sponsor of Chicago at a Crossroads. Their support has helped the Chamber convene influential voices, foster important conversations, and create a forum where business and civic leaders can come together to address the opportunities and challenges facing our region. As Chicago continues to evolve, Chicago at a Crossroads remains committed to elevating the ideas, investments, and collaborations that will define the city’s next chapter.
Watch the highlight video below covering the past year of Chicago at a Crossroads: