Photo Credit: Lindsay Angelo.
When the dot-com era landed in the late 1990s, businesses and workers faced a pivot that rarely felt like a real choice at the time: embrace the technology early, or kick the can down the road until adoption stopped being optional. A quarter-century later, artificial intelligence is presenting Chicago and the human population at large with the same pivot, and this year, the city’s most influential institutions have started to fully embrace the AI era.
At the civic level, the approach is infrastructure-focused. The city of Chicago has published a formal AI roadmap for municipal services, with the city already piloting AI-assisted road sensors for pothole detection and eyeing similar tools for snow and trash operations. Illinois lawmakers, meanwhile, have passed what advocates call one of the strongest AI safety laws (SB0315) in the country, signaling that the state wants guardrails to keep pace with adoption rather than trail it. The research infrastructure is scaling to match: the University of Illinois System closed on a 244,954-square-foot West Loop building this year to permanently house the Discovery Partners Institute, pairing Urbana-Champaign’s research muscle with Chicago’s industry scale, while P33 keeps positioning the city as a destination for AI talent through events like Chicago AI Week.
In classrooms, the posture is similarly pointed foward. Chicago Public Schools reports that 85 percent of teachers and 86 percent of students already used AI tools last year, under district guidance that frames the technology as a collaborator with instruction, not to take place of it, a notably different bet than the $55,000-a-year private AI school now enrolling students blocks away.
But the clearest expression of Chicago’s mindset sits on the South Side. In November, the Chicago Urban League opened its Empowerment Center in West Chatham, a 15,000-square-foot former Walmart training facility donated to the organization, now teaching residents AI prompting and engineering alongside its long-running entrepreneurship coaching. The pairing is deliberate: as AI-skilled job postings multiply nationally, the Urban League is treating AI literacy as a key element for economic infrastructure growth, not a luxury reserved for downtown offices. Chicago Public Library has taken a similar stance, partnering with the AI Safety Awareness Project on free workshops for general audiences and seniors alike, no experience required, alongside its existing CyberNavigator tech support and free LinkedIn Learning access for cardholders.
For entrepreneurs, nonprofits like Sunshine Enterprises in Woodlawn have folded AI and digital tools into their Community Business Academy, treating tech fluency as part of what it takes to launch and sustain a business in an under-resourced neighborhood, not a separate track for the already tech-savvy. Similarly, the entrepreneurship hub, TBM360 Build-A-Thon, led by Cassiopeia & Dre Meekins, hosts a weekly live hands-on workshop for business owners ready to scale and action-takers who need structure and guidance in an AI world.
Still, the aspects of the picture are blurry. Nationally, roughly 68 percent of small businesses now use AI in some capacity, mostly for ad hoc tasks like marketing copy or customer emails, and Black-founded startups raised roughly $643 million by this spring, the strongest quarter in years, yet concentrated in a handful of outsized deals rather than broad-based access to capital or seed funding.
The dot-com era eventually forced everyone’s hand, whether they were early adopters or not. Chicago’s institutions, from City Hall to classrooms to workforce and entrepreneurial empowerment centers, aren’t waiting to find out what that costs this time.
J’Arnay Harris covers entrepreneurship, culture, and the intersections of race, ambition, and power through an intergenerational lens. She writes with a sharp eye for the uncomfortable truths that get smoothed over in mainstream narratives, examining what success really costs in a modern world.
