Chicago residents often face lengthy waits and complicated processes when interacting with city services, a challenge highlighted by an audit from the Chicago Office of the Inspector General that described the city’s 311 system as a “black hole” lacking transparency and efficient tracking for service requests. This contrasts sharply with the rapid adoption of artificial intelligence (AI) technologies in the private sector, where businesses use AI-driven voice agents, automated document processing, and identity verification tools to streamline customer service.
A Chicago-based AI startup CEO and former tech entrepreneur says that city government could similarly transform its operations by integrating AI, starting with 311 services. The executive points to examples in other cities and governments that have begun leveraging AI: the British government is hiring specialists to deploy AI solutions on public issues, and New York City recently created a team of 30 technologists to develop digital tools for municipal agencies. Midland, Texas, a smaller city, eliminated 7,000 missed calls by deploying a voice agent to handle routine inquiries around the clock and in multiple languages, suggesting a scalable solution for Chicago.
Beyond phone systems, AI technologies known as large language models can improve document review processes, potentially speeding up applications for permits and licenses. For instance, Chicago’s current method for issuing guest parking permits requires form submission, scanning and emailing documentation, followed by a review period of several weeks before the permits arrive by mail. Using AI to verify proof of residency automatically and flag irregular cases for human review could enable same-day printing and mailing.
The Department of Buildings also stands to benefit significantly from AI. With only a few dozen inspectors responsible for investigating tens of thousands of complaints each year, unresolved violations have been linked to preventable fire incidents in the city. Stockton, California, recently piloted an AI program that scanned complaints and ranked violations for inspection, uncovering 4,000 issues in just five days. Applying similar techniques could prioritize life safety risks for Chicago inspectors more efficiently.
However, caution is warranted. Cook County’s recent property tax modernization effort, which doubled its budget and caused delays affecting tens of thousands of property owners, illustrates the challenges local governments face when implementing large-scale technology projects. According to the county inspector general’s report, obstacles include restrictive hiring and procurement policies that limit in-house technical expertise and an overreliance on single vendors, often leading to costly, multi-year customization projects that stifle iterative development.
To avoid these pitfalls, the AI startup CEO recommends that Chicago’s next mayor build a small team of skilled engineering and product leaders dedicated to managing vendor relationships and deploying high-impact applications. Rather than hiring large internal development teams, officials should engage multiple startups to run parallel pilot projects focused initially on high-volume, low-risk services. Contracts should emphasize results, such as resolved calls and reduced backlogs, with delivery risk borne by vendors.
Such an approach could position Chicago as a national leader in applying AI to improve local government services, reducing wait times and enhancing residents’ experiences with the city. The startup CEO stresses that with focused leadership and modern technology, months-long delays in obtaining simple permits could become a thing of the past.