Business, technology, and civic leaders convened at the University Club of Chicago on March 3, 2026, for Chicago at a Crossroads: Securing Chicago’s AI Advantage, a luncheon forum presented by Old National Bank and hosted by the Chicagoland Chamber of Commerce. The event brought together senior executives and AI practitioners to examine how Chicago can translate world‑class research and major place‑based investments into real economic and workforce impact.
In opening remarks, Jack Lavin, President and CEO of the Chicagoland Chamber of Commerce, framed the moment as both urgent and consequential. AI, he noted, is no longer theoretical or distant. It is already reshaping how businesses operate, how workers perform their jobs, and how cities compete. The question facing Chicago is not whether AI will transform the economy, but whether the region is prepared to lead that transformation.
Lavin then welcomed moderator Jessica Smith, CEO and Managing Partner of Jasculca Terman Strategic Communications, along with panelists Jason Birnbaum, Chief Information Officer of United Airlines, and Dagar Katyal, Principal Generative AI and Machine Learning Specialist at Amazon Web Services.
AI Has Moved from Experimental to Operational
A central theme of the discussion was that AI is no longer confined to pilots or proofs of concept. For leading organizations, AI is already embedded in mission‑critical operations, delivering tangible value at scale.
Birnbaum shared how United Airlines is using generative AI to transform customer communication during disruptions. The airline’s Every Flight Has a Story initiative was designed to give passengers clear, transparent explanations when things go wrong, but it initially struggled to scale. As he put it, “the problem was we couldn’t scale. Only 10% of the actual flights that needed this kind of message actually got it. So, enter AI, and we were able to use generative AI to read operational data and provide well over 50% of our flights with this transparent information.”
AI is also reshaping United’s internal operations, where real‑time decisions can have cascading effects across crews, aircraft, and customers. “It enables us to run a much more efficient operation,” Birnbaum said, describing how AI now helps prioritize which planes land when capacity is constrained, based on downstream impacts.
Katyal reinforced that same shift from experimentation to execution from Amazon’s perspective. “What has changed with the advent of generative AI is generative AI has taken a lot of the heavy lifting away from us when it comes to writing those documents,” he said, noting that AI now filters vast datasets so teams can focus on decisions rather than data processing. Across both organizations, the message was clear: AI is already operational infrastructure.
Workforce Adoption Is Inevitable and Expectations Are Shifting Fast
The conversation repeatedly returned to people, not just technology. Panelists emphasized that employee expectations around AI are changing quickly, and organizations must adapt just as fast.
Birnbaum likened the current moment to the early days of smartphones, when personal technology outpaced enterprise adoption. “How long before you think you’re going to have the same expectations of what you do at work are going to catch up with what you’re doing at home?” he asked. “I think it’s not going to be very long… it’s going to be table stakes.”
He went further, warning that AI literacy will soon be as fundamental as email. “If you’re not using it in your company, your company’s going to be behind, and if your employees aren’t using it, they’re not going to be particularly good employees,” he said. In that framing, the challenge for leaders is not whether to adopt AI, but how to prepare their organizations and people to use it responsibly and effectively.
Katyal echoed this sentiment, particularly around generational dynamics. “The younger generation… they are the first ones to adapt to that change, and they are the people who are able to use AI in the most effective way,” he observed. While adoption curves differ, both speakers emphasized that enthusiasm for AI is widespread, especially when it removes mundane tasks and allows people to focus on higher‑value work.
Responsible AI Requires Action, Not Paralysis
The final takeaway focused on governance, risk, and responsibility. While both panelists emphasized the importance of guardrails, they cautioned strongly against letting the pursuit of perfection delay progress.
Katyal framed responsible AI around transparency and human accountability. “If you can explain the way AI is being used, whether AI is AI assisted, whether it’s AI guided, whether it’s AI decided… that’s like a first step of responsibility,” he said. He added that organizations must remain accountable for AI‑driven decisions, rather than deflecting responsibility onto technology.
Birnbaum offered a blunt warning against unrealistic risk standards, drawing from a discussion at United’s board level. “If your measurement is zero risk and perfection, then you will never do it, and you will miss out,” he said. He reminded the audience that human systems are imperfect as well. “Humans make mistakes all the time… if we set the bar to say we need to be better than the humans and make sure we always have a human in the loop, but still take sufficient risk to move forward, then that is probably the right place.”
Both speakers stressed that waiting until data, processes, and governance are flawless is not a viable strategy in a rapidly evolving landscape. The cost of inaction, they argued, may be far greater than the risks of moving forward thoughtfully.
A Catalyst Moment for Chicago
Taken together, the discussion at Chicago at a Crossroads made clear that AI is a present‑day force reshaping competition, work, and public systems. As Jack Lavin noted, Chicago already has the assets to lead, what remains is execution. If businesses, educators, and policymakers act on these insights, the region can position itself not just as a participant in the AI economy, but as a national model for how innovation, trust, and workforce resilience advance together.
View the full photo gallery from the event here.
