
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?

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]
- Related: All about TIFs. [City Cast Chicago 🎧]
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What To Do
Monday, Aug. 18
- 🔈 2025 Sonic Pavilion Festival | Millennium Park
- 🧙🏽 “Wicked” | Churchill Field Park | Wicker Park
- 🎷 Jazz’n in the Park | South Shore Cultural Center
- 🌅 Summer & Fall Afterwork Sunset Cruises on Lake Michigan | Anita Dee | DuSable Harbor
- 🐇 "White Rabbit Red Rabbit" | TUTA Theatre | Ravenswood
- ⚾️ Cubs vs. Brewers | Wrigley Field
- ♦️ Magic Mondays | iO Theater | Lincoln Park
- ✍️ Zen Coloring for Adults | Harold Washington Library | Loop
- 🤘 Punk Rock Mondays | Delilah’s | Lincoln Park
- 🕺🏻 Free Mondays | 9 p.m. | Free | Ukrainian Village
Tuesday, Aug. 19
- 💃🏻 Tuesdays on the Terrace | Museum of Contemporary Art Chicago | Streeterville
- 🧪 Science Social | Green Eye Lounge | Bucktown
- 👠 “13 Going on 30” | Rooftop Cinema Club | Fulton Market
- 🏀 Sky vs. Storm | Wintrust Arena | McCormick Square
- 🦜 Guided Exhibition Tour: "Winging It" | Newberry Library | River North
- ⚾️Brewers vs. Cubs | Wrigley Field
- 🎵 Zander Raymond & Saapato | Comfort Station | Logan Square
- 🚲 “Bike Vessel” | Dawes Park | Auburn Gresham
- 🎷 Heisenberg Uncertainty Players | Fulton Street Collective | West Loop
- 🍽️ Maria’s Patio Jam | Maria’s Packaged Goods & Community Bar | Bridgeport
- ✈️ “Top Gun” | Mary Bartelme Park | West Loop
- 💪 Backyard Basics Fitness Club | 1928 N. Richmond St. | Logan Square
- 🍺 Tipsy Trivia | Daisy’s Po-Boy and Tavern | Hyde Park
- 🧱 LEGO Night | Blackstone Branch | Kenwood
- 🍷 Petra van Nuis & Andy Brown Duo + Pre-Concert Wine Tasting | Colvin House | Edgewater
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