
City Cast Chicago
💸 A ‘loser tax’ on Chicago sports teams?
October 21, 2025 · — Simone
Hey Chicago! Executive producer Simone Alicea in for Emmi. We’re intrigued by Chicago magazine’s, uh, creative ideas for closing the city’s budget deficit. In fact, we offer a couple of our own — including a tax on sports teams that lose too many games — in today’s podcast episode.
Take a listen, and hit us up if you’ve got some other proverbial couch cushions Chicago should be turning over.

What's CITY Talking About

No Kings and Court Updates
Saturday’s No Kings rally drew over 100,000 people to downtown Chicago. On today’s pod, we’re breaking down the demonstration and updating listeners on what’s going on in Chicago’s federal courts. [City Cast Chicago 🎧]
- Related: On Monday, a judge questioned ICE and Border Patrol leaders about tear gas and aggressive raids. [WTTW]

Stacy Davis Gates to Lead State Teachers Union
The Chicago Teachers Union head was elected president of the Illinois Federation of Teachers and will retain both posts. She has long pushed for more state funding for public schools, but says she’ll also prioritize issues like health insurance and pensions. Until 20 years ago, CTU presidents often held both roles. [WBEZ]
Salt Shed Seeks Expansion
The music venue's developers are looking to buy an adjacent property along the North Branch of the Chicago River near Goose Island. Just how big could the new outdoor space get? Try 15,000 people for concerts and street fests — nearly three times its current capacity. [Crain’s 🔒]
Keeping Carp From Invading Lake Michigan
Despite funding tension with the feds this year, the state has acquired land for the Brandon Road Interbasin Project — a big step for the planned underwater defense system against invasive carp. The upgrades in the Des Plaines River will include a bubble wall, acoustic blasts, an electric barrier, and a flushing mechanism to keep the fish from passing through and potentially overtaking native species. [Grist]
- How else can we keep carp from spreading? Eat them. [City Cast Chicago 🎧]
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Final Round: The Scariest Thing in Chicago

We’ve reached the final round of our bracket to crown the scariest thing in Chicago. It’s a matchup between one of our most common anxiety dreams and Chicago’s mysterious underground.
Which one frightens you the most? Vote in our poll, and we’ll release the winner next week.

What To Do
Tuesday, Oct. 21
- 🎥 Chicago International Film Festival | Various locations
- 🎭 "The Sound of Music" | James M. Nederlander Theatre | Loop
- 🍷 Fall Vibes Sip & Paint | Vault Gallerie | Pilsen
- 🎞️ "M3GAN" | Jeffery Manor Branch | South Deering
- 🔑 Tinker Tuesday: Beaded Fidget Keychains | Lincoln Belmont Branch | Roscoe Village
- 🧛 Drunk Dracula | Drunk Shakespeare Chicago | Loop
- 🎶 Garbage | Rate Field
- 🎤 Show & Tell for Grown-Ups | Heritage Bikes & Coffee | Lakeview
- 🧛 “Nosferatu” | Davis Theater | Lincoln Square
- 🎤 The Moth StorySLAM: Go, Team! | FitzGerald's | Berwyn
Wednesday, Oct. 22
- 🎉 Wednesday Addams & Thing Creepy & Kooky Party! | MLK Skating and Bowling Center | Auburn Gresham
- 🎥 Chicago International Film Festival | Various locations
- 🎭 "Mr. Wolf" | Steppenwolf Theatre | Lincoln Park
- 🕺🏻 Pisco Disco | Tanta Cocina Peruana | Streeterville
- 🧛 “The Addams Family” | Gallagher Way | Wrigleyville
- 🎤 Benny the Butcher | Avondale Music Hall
- 🌸 Wednesday Wind Down with Music | Garfield Park Conservatory
- 🛍️ Hex and The City a Spooky Market | Barcocina | Lakeview
- 👻 Lincoln Park Ghost Tour | Chicago History Museum
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I’ll leave you with this image of one of Teatro ZinZanni Chicago’s dazzling aerial performers. The experience in the tent at the top of the Cambria Hotel might just be your best date night ever.
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