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How Could ChatGPT Help You Navigate Chicago Bureaucracy?

Posted on January 24, 2024   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

The Chicago City Hall building

The Chicago City Hall building. (Beata Zawrzel / NurPhoto / Getty)

City Cast

How Well Does ChatGPT Know Chicago?

00:00:00

Who hasn’t struggled navigating the City of Chicago’s website?

South Loop AI developer and activist Marley Rosario has spent hours trying to answer questions from how to register for a protest permit to getting block party permissions.

That’s why Rosario created ChicagoGPT, a custom version of the popular ChatGPT. In two days, the Chicago native scraped the city’s sitemap in hopes of making the city resources more accessible.

What Can ChicagoGPT Answer?

Early testers found they could get help registering for a block party, submitting a FOIA request, and even paying a parking ticket. (Though, Rosario doesn’t recommend doing the last one for security reasons.)

But only those with premium ChatGPT Plus subscriptions can play with ChicagoGPT, which isn’t up to Rosario but ChatGPT owner OpenAI.

What Are the Limits of ChicagoGPT?

“It’s good at taking a lot of data, synthesizing it, and then regurgitating it back to you,” Rosario said. “But it’s not great at finding very specific pieces of information and referencing it directly back to you.” 

For example, ChicagoGPT would be able to summarize press releases about Chicago’s sanctuary city status. But in other cases, it’s faster to probably just call 311 or Google.

Should the City Consider Using ChicagoGPT?

Looking to Southern cities as an example, Rosario said there’s a big market for city GPTs because of its affordability for local governments and accessibility for residents. That’s why Rosario is also working on a similar tool for New York City. 

“If I was a betting man, I definitely think that it would be a missed opportunity for the city of Chicago not to do something [with ChatGPT],” he said.

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