
City Cast Chicago
'Midway Blitz' one month in
October 10, 2025 · — Emmi Mack
So, Chicago. We’re officially one month into Operation Midway Blitz. Man, it feels a lot longer than that.
It was a month full of tear gas, rubber bullets, smoke bombs, handcuffs, and mass raids. The feds say over 1,000 people have been arrested … and that’s without “protection” from the National Guard.
Today’s news quiz touches on some of that turmoil. And as the operation continues, we’ll continue delivering updates straight to your inbox 📤

What Chicago's Talking About
Judge Blocks National Guard from Chicago
A federal judge has temporarily blocked the deployment of National Guard troops in Chicago, saying they would add “fuel to the fire.” U.S. District Judge April Perry initially said she was granting the restraining order in part, but a written ruling should come today. [Hey Chicago 💻]
- Related: A judge also ruled the feds can't tear-gas journalists. [Block Club]

Troops in Chicago, the Transit Crisis, and Bears’ Rematch
In addition to the recent ruling on the National Guard, a federal judge ruled against ICE’s arrest tactics. We’re breaking all of it down on today’s podcast along with The Triibe’s Corli Jay. Also discussed: transit woes, da Bears, and a new wine bar on 75th Street. [City Cast Chicago 🎧]
Chicago Cultural Commissioner Leaves Post
Chicago’s cultural commissioner Clinée Hedspeth has resigned from her post at City Hall after 18 months. An ally of Mayor Brandon Johnson, her tenure was marked by accusations of bullying. Last spring, more than 140 artists called on Johnson to address it. [Sun-Times]
This Week’s Must-Read
Did you know Illinois was the first state to ban book bans? Still, as America reckons with new forms of censorship, Chicagoland writers observe Banned Books Week. Here, some recall the banned books from their own youths. Famous titles include “The Autobiography of Malcolm X,” “Perks of Being a Wallflower,” “Captain Underpants,” and “The Bluest Eye.” [Third-Coast Review]
- Love these books? Peruse Chicagoland’s best indie bookstores. [Hey Chicago 💻]
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Your Chicago News Quiz

Increased ICE activity has defined the last month in Chicago — all while other local stories keep breaking. Were you paying attention?

What To Do
Friday, Oct. 10
- 🎥 Better Cities Film Festival | AMC Dine-In Block 37 | Loop
- 👟 Brooks Running Pop-Up | Pioneer Court | Streeterville
- 🍽️ Aging Well | Kehrein Center for the Arts | Austin
- 🎤 Chance the Rapper | Huntington Bank Pavilion | Northerly Island
- 🎞️ Celluloid Now | Gene Siskel Center | Loop
- 🎃 Night Of 1,000 Jack-o'-lanterns | Chicago Botanic Garden | Glencoe
- 🎤 Iliza Shlesinger | Chicago Theatre | Loop
- 🤠 Hard Country Honky Tonk | Empty Bottle | Ukrainian Village
- 🔊 Flosstradamus | Ramova Theatre | Bridgeport
- 🎶 Aly & AJ | Salt Shed | Goose Island
- 🎃 Glass Pumpkin Patch | Morton Arboretum | Lisle
- 🧶 Mayan Textiles: Art, Tradition, and Technique | National Museum of Mexican Art | Pilsen
- 👠 reFashioning History Exhibition | Charles Gates Dawes House | Evanston
- 👗 Fall Clothing Swap Preview Party | Chicago Fair Trade Museum | Uptown
Saturday, Oct. 11
- 🚗 Slow & Low: Chicago Lowrider Festival | Navy Pier
- 🎉 Indigenous Peoples Day Celebration | Dvorak Park | Lower West Side
- 🎥 Better Cities Film Festival | AMC Dine-In Block 37 | Loop
- 🥂 Brunch Fest | Lincoln Avenue between Diversey and Wellington | Lincoln Park
- 🛍️ Englewood Village Market | 58th and Halsted
- 🏳️🌈 OUT at CHM Walking Tour: North Side LGBTQIA+ Stories | Belmont Red Purple Brown Line | Lakeview
- 🍺 Oktoberfestiversary | Between Begyle and Dovetail | Ravenswood
- 🚶🏻♀️ Walking Tour: Historic Old Town | Chicago History Museum | Lincoln Park
- 🌮 Tacoberfest | Big Star | West Town
- 👟 Brooks Running Pop-Up | Pioneer Court | Streeterville
- 🎃 Glass Pumpkin Patch | Morton Arboretum | Lisle
- 🚶🏻♀️Walking Tour: Paseo Boricua and Humboldt Park | Ciclo Urbano
- 🎤 GrandSLAM Championship | Athenaeum Center | Roscoe Village
- 🎞️ Celluloid Now | Gene Siskel Center | Loop
- 🎃 Night Of 1,000 Jack-o'-lanterns | Chicago Botanic Garden | Glencoe
Sunday, Oct. 12
- 🏃 Chicago Marathon | Various neighborhoods
- 🎉 Chicago Sukkah Design Festival | James Stone Freedom Square | Lawndale
- 🎷 A Jazzy Evening in Red | Wild Blossom Meadery and Winery | Washington Heights
- 🎥 Better Cities Film Festival | AMC Dine-In Block 37 | Loop
- 👟 Brooks Running Pop-Up | Pioneer Court | Streeterville
- 🌮 Tacoberfest | Big Star | West Town
- 🍺 Oktoberfestiversary | Between Begyle and Dovetail | Ravenswood
- 🛍️ Sunday Market + Fall Fest | Jefferson Memorial Park | Jefferson Park
- 🐶 Dogtober Fest | Midwest Coast Brewing | Near West Side
- 👻 La-Booo-Bu Bash: Halloween Themed Market | 1706 S. Halsted St. | Pilsen
- 🎃 Glass Pumpkin Patch | Morton Arboretum | Lisle
- 🍻 Kolsch Service | Salt Shed Pub | Goose Island
- 🎞️ Celluloid Now | Gene Siskel Center | Loop
- 🎶 Dondria | Epiphany Center for the Arts | West Loop
- 🎃 Night Of 1,000 Jack-o'-lanterns | Chicago Botanic Garden | Glencoe
- 🎵 AAAYYYAAA | Empty Bottle | Ukrainian Village
And finally, a happy image to close out the week: three robins on a drinking fountain in Peterson Park (which also has an excellent nature center for leaf-peeping).

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