City Cast Chicago
🤼 Let Chicago's budget battle begin
October 20, 2025 · — Emmi Mack
Hey Chicago! The Chicago International Film Fest continues this week — recs to come. And for you fellow horror heads, the Music Box of Horrors: Dead and Loving It! series goes through Oct 31. (“Addams Family Values” was packed the other night, preceded by plenty of Morticia Addams drag.)
For now, onto markedly less fun news. It’s budget season 👇
What's CITY Talking About
Feds Raid Swap-O-Rama Flea Market
At least 15 people were detained by federal agents Thursday at Swap-O-Rama. The flea market in Back of the Yards features many Hispanic vendors. Video footage from the raid captures the crowd’s warnings: “ICE, ICE, La Migra.” [Sun-Times]
- Related: Swap-O-Rama is a Chicago tradition. [City Cast Chicago 🎧]
Protestors Say State Police Led Them Into Broadview Street — And Attacked Them
On Friday, Illinois State Police ushered a crowd of about 100 protesters at the Broadview ICE facility into the street. They then attacked them with billy clubs, according to activists. Illinois State Police say they arrested 11 people after demonstrators “repeatedly blocked a street,” creating a safety hazard. [Block Club]
- Related: What are the state police doing in Broadview? [WBEZ]
Chicago’s Federal Court Reduces Operations Amid Shutdown
Chicago’s Dirksen U.S. Courthouse has run out of money to pay staff for nonessential duties. Now, several jury trials are being canceled, including some high-profile ones. [Tribune 🔒]
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What To Do
Monday, Oct. 20
- 🎥 Chicago International Film Festival | Various locations
- 🕺🏻 Free Mondays | Empty Bottle | Ukrainian Village
- 💥 Pocket Con 2025 | Chicago History Museum | Lincoln Park
- 🤘 Punk Rock Mondays | Delilah’s | Lincoln Park
- 🤣 Adam Sandler | United Center | Near West Side
- 🎵 Neon Trees | House of Blues | Loop
- 💤 Mellow Mondays | Woodson Regional Branch | Washington Heights
- 🎃 Pumpkin Carving With Wild Turkey | The Duck Inn | Bridgeport
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
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We have lots of resources on bird-watching in Chicago, but if you want to go on a different kind of birding expedition, check out this guide to Tony Fitzpatrick’s pieces around the city. The late artist’s work remains a Chicago fixture.
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