City Cast Chicago
🎃 Your guide to October in Chicago
October 1, 2025 · — Emmi Mack
Hey Chicago! It’s been an intense week. ICE agents swarmed downtown Sunday, detaining multiple people. The next day, Gov. JB Pritzker said the Department of Homeland Security requested military troops come to the state. Stay tuned — City Cast Chicago will keep you up to date on developing stories.
We’ll also continue spotlighting good news alongside it all. Because being a Chicagoan means seeing, and celebrating, what makes this city great even when the going gets extra tough.
That’s why, now, in the final days of our fall membership campaign, we’re asking for your help to reach our membership goals and sustain this daily newsletter.
It costs to keep all this content free! When you become a City Cast Chicago Neighbor, you’re helping sustain the journalism that connects us all.
Also: Anyone who joins this week gets a “Neighbors Make Chicago” tote bag. Won’t you join us?
What's CITY Talking About?
Chicagoans Protest ICE on Wacker Drive
Hundreds gathered downtown last night, filling part of Wacker Drive near Michigan Avenue, to protest the increased presence of U.S. Immigration and Customs Enforcement agents. Organizers include the Chicago Teachers Union, the Coalition Against the Trump Agenda, and United Working Families. [WGN]
- Early Tuesday: ICE raided a South Shore apartment, dragging out people, including children, who were undressed. [Block Club]
What Happened to the Family Detained From Millennium Park?
Two young siblings were playing in Crown Fountain when their family was approached by immigration agents Sunday. The entire family was taken from Millennium Park in front of a crowd of onlookers. Now, the mother and children are confined at O’Hare; the father is in Broadview. They await transfer to Texas and, eventually, deportation to Guatemala. [Tribune 🔒]
Trump Wants to Use Chicago as Military ‘Training Grounds'
In a meeting with military leaders in Quantico, Virginia, President Donald Trump said he wants to use “dangerous cities as training grounds” for the military. He continued the vague threat, saying, “we’re going into Chicago very soon.” [Sun-Times]
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What To Do
Wednesday, Oct. 1
- 🎭 "rustbelt." | Redtwist Theatre | Edgewater
- 🦢 "Swan Lake" | Harris Theater | Loop
- 🌸 The Promise of Spring | DePaul Richardson Art Gallery | Lincoln Park
- 🎆 Bottomless Margaritas & Fireworks on the Riverwalk | Island Party Hut | River Walk
- 🕺🏻 Pisco Disco | Tanta Cocina Peruana | Streeterville
- 📖 Re-Centering Native Women in Zhegagoynak (Chicago) History | Newberry Library | Near North Side
- 💪 HIIT | Gallagher Way | Wrigleyville
- 🎥 “In Time” | Austin Branch
Thursday, Oct. 2
- 🍎 Farmers Market | Daley Plaza | Loop
- 🎥 "Shared Resources" | Siskel Film Center | Loop
- 👑 Queens Of The Stone Age | Chicago Theatre | Loop
- 🎶 Destroyer | Thalia Hall | Pilsen
- 💃 Cascada | Des Plaines Theatre
- 🍌 Farmers Market | Yukich Fields | Evergreen Park
- 🎵 Sombr | Radius | Pilsen
- ⭐️ 2hollis: The Star Tour | The Salt Shed | Goose Island
- 🍷 Port Wine Fest Chicago | The Walden | Near West Side
💞 Finally, a heartfelt thank you to our many new City Cast Chicago Neighbors: Bonnie E., Jojo B.S., Jillian E., Suzy J., Katherine S., Destini V., Christal G., Alyssa E., Serena M., Lauren M., Jeannine S., Maura B., Victoria S., Michael K-P., and Sarah W.!
Welcome to the Neighborhood!
Want to join them? Become a City Cast Chicago Neighbor today — and get your special-edition tote bag.
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