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City Cast Chicago

City Cast Chicago

😭 Why is Chicago so broke?

August 18, 2025 · — Emmi Mack

Hey Chicago … I’m looking for a guy in finance. Just kidding, not really my type. But lots of women in Chicago are. Some of them recently gathered for speed dating in West Town, alongside plenty of investment bankers from the Gold Coast. Here are the highlights.

Now, onto other kinds of financial news 👇

What's CITY Talking About?

Podcast Player: "Why Is Chicago So Broke?"

Why Doesn't Chicago Ever Have Enough Money?

Our city, our schools, and our transit system are all in financial crisis. On today’s podcast, we’re asking why. Justin Marlowe, a professor at the University of Chicago professor and director of the Center for Municipal Finance, joins to discuss how Chicago’s public institutions got here. [City Cast Chicago 🎧]

Lawmaker Promises Transit Bailout in Fall

State Rep. Kam Buckner says he is “convinced” lawmakers will pass a transit bailout during the fall veto session. He also floated the idea of an event surcharge, which could add between $1 to $3 to concert and game tickets to help pay for public transit. [Sun-Times]

Illinois’ Rental Assistance Program Is Back

Though the program recently had a third of its funding cut, Illinois’ state rental assistance program is back open. It began in 2020 using federal pandemic aid. Now, it’s paid for by the state with $50 million in funds available. Eligible tenants must make 80% or less of the area median income. The income cap for households of four is $95,900. [Tribune 🔒]

Pilsen Says No to Expanding TIF District

Pilsen residents are against expanding the neighborhood’s tax-increment financing district. Nearly 2,000 residents voted in a survey, and about 80% opposed the controversial measure, which has stalled twice at City Council. Now, it appears Ald. Byron Sigcho Lopez (25th) is moving away from the idea. [Block Club]

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