
City Cast Chicago
🅿️ Chicago’s worst deal ever could get slightly better
September 28, 2026 · — Jessica Pupovac
Hi! Jessica Pupovac here, filling in for Emmi. I hope you’re all still riding the high from the Sox-Cubs clinching back-to-back playoff berths – and the off-the-chain celebration that followed (especially for Munetaka Murakami 💯)! It’s gonna be a fun October. 🤞

What's CITY Talking About

Glimmer of Hope in Our Parking Deal Nightmare
City Council could vote this week to approve a sale of the city’s parking meter rights, this time with a twist: the new contract would give the city a 5% cut of future “calculated net income.” It’s a far cry from regaining control, but it’s better than nothing (which is what we currently get). [Block Club]
- Not so fast: Some alders think the city could do better and are working to delay the decision.
- How we got here: The worst deal Chicago ever made. [City Cast Chicago 🎧]
Mayoral Candidate Lawsuit. Plus, Ford City Going Industrial
Mayoral candidate Bill Quinlan’s lawsuit aims to block Illinois Secretary of State Alexi Giannoulias, U.S. Rep. Mike Quigley, and Cook County Treasurer Maria Pappas from seeking reelection in their offices while running for mayor. On today’s podcast, we break down the details. Plus, City Council approves plans for the future of the Ford City Mall site. [City Cast Chicago 🎧]
Chicago’s Asylum Seekers Face Stiff Odds
Approval rates for immigrants seeking asylum in Chicago have plunged to 3.3% this year, as the Trump administration has imposed strict new rules and fired or replaced several career judges. A former assistant chief of immigration court calls it “a mass catastrophe against due process.” [Sun-Times]
CPS Enrollment Continues Freefall
In line with national trends, Chicago Public Schools enrollment is down yet again. About 304,000 students are currently enrolled, which amounts to 11,500 fewer than last year and roughly 76,000 less than a decade ago. Declines are hitting the city’s South and West Side schools the hardest. The Chicago Teachers Union is calling for an extension of the moratorium on school closures, which is set to expire at the end of this school year. [Chalkbeat]
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Neighborhood Shoutouts
Now it's time for a neighborhood shoutout where our City Cast Chicago Neighbors share their recs for places to try and things to do across the city!
Today’s shoutout comes from Neighbor Jenn A. in Woodlawn:
“Yassa African Restaurant in Bronzeville is so delicious! It is in the path of my daily commute, but I had never stopped until this week. It will be a part of my regular rotation.”

What To Do
Monday, Sep. 28
- 🚲 All-Wheels Ride | Senka Park | Gage Park | Free
- 🏈 Bears vs. Eagles | Soldier Field | Museum Campus
- 💃 Art of Being: Dance Movement Workshop | Chicago Danztheatre Ensemble | Andersonville
- 👗 Color Analysis | Mood Fabrics Showroom | Loop
- 🪄 Magic Mondays | iO Theater | Near North
- 🎤 Best of Second City | Second City Main Stage | Old Town
Tuesday, Sep. 29
- 🧠 Brain Health Tuesdays | Avalon Park Branch | Free
- 🌏 World Music Festival | South Asia Institute | South Loop | Free
- 🃏 Deal Me In | Kelly Branch | Englewood | Free
- 🎶 Mon Rovîa | Salt Shed | Goose Island
- 🎸 Poolish / Daundry / Double Extra Large | Empty Bottle | West Town
- 🎺 Balourdet Quartet | The CheckOut | Uptown
The changing weather makes me want to bust out some card games. I’m intrigued by this new creation from a Chicago high schooler, which is designed to spark constructive, thought-provoking, and sometimes ridiculous debates around the kitchen table. (Though I could imagine it being an excellent, if somewhat dangerous, bar game, too.)
Free · Daily

