
City Cast Chicago
💸 Pritzker made HOW MUCH playing blackjack?!
October 17, 2025 · — Emmi Mack
Hey friends! Do you like having the day’s news summarized by the time you wake up? Do you like perusing our hand-picked events over coffee? Do you like me?
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What's CITY Talking About
Federal Agents Must Wear Body Cams in Chicagoland
A judge ruled that immigration agents must wear body cameras in and around Chicago as immigration agents continue aggressive tactics against locals. The judge said she was a “little startled” over what she’s seen on TV. [WGN]
- Related: That’s not the only restriction judges are putting on agents. [Hey Chicago 💻]

Tear Gas Continues — Also a Promontory Farewell
Another week, another violent encounter with ICE in Chicago. On today’s podcast, Block Club’s Francia Garcia Hernandez and TV host Brandon Pope break down what we know after federal agents caused a crash on the city’s Southeast Side. [City Cast Chicago 🎧]
- Related: How to help neighbors amid ongoing ICE raids. [Block Club]
Pritzker Made $1.4M Playing Blackjack in Vegas
As if Gov. JB Pritzker didn’t have enough money, tax returns reveal the billionaire made over $1 million playing cards in a casino. He says he’ll be donating the winnings to charity. Though the governor and his wife reported $10.6 million in income last year, his net worth rests around $3.9 billion. [NBC]
This Week’s Must-Read
"Extralegal detention and law enforcement terrorism are as native to Chicago as deep-dish pizza and ketchup-free hot dogs," Vic Mensa writes in an op-ed. The hometown musician draws connections between Chicago's historic racial divisions, the recent arrival of migrants, and what he calls "a crisis of conservative design."
- Don’t forget: There’s a No Kings protest tomorrow.
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Your Chicago News Quiz

We’re trucking along here in Chicago. Neighbors are stepping up as ICE terrorizes neighborhoods. Another No Kings protest is scheduled for tomorrow. And, amidst it all, vibrant art events continue throughout the city.
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In two hours, this could be you.
Time to unwind is at a premium. That’s why your next getaway should be to somewhere affordable, easy to reach, and packed with fresh-air fun. Madison, Wisconsin checks every box. This road trip guide includes a packing list, restaurant picks, and even a playlist for your journey.

The Spooky Bracket Continues!
As spooky season creeps on, it’s time for round two of our bracket on (some of) the scariest things in Chicago.
Vote on which of these Chicago experiences gives you the chills! We'll be back with the final round soon.


What To Do
Friday, Oct. 17
- 🎉 Hispanic Heritage Month Celebration | Humboldt Park
- 👂 Ear Taxi Festival and Chicago Fringe Opera present Soper, Baiocchi, and Barnes | The Kehrein Center for the Arts | Austin
- 🎥 Chicago International Film Festival | Various locations
- 🍺 SAUCED Night Market | Half Acre Beer Co | Bowmanville
- 👠 Shadow and Silk Fashion Gala | The Congress Hotel | Loop
- 💀 "The Nightmare Before Christmas" | Drake Hotel | Loop
- 💃 Output | Elastic Arts | Logan Square
- 🏒 Pucks for Autism | United Center | Near West Side
Saturday, Oct. 18
- 🎃 Arts in the Dark Halloween Parade | State Street between Lake and Van Buren | Loop
- 🏠 Open House Chicago | Various locations
- 🛑 No Kings | Grant Park | Loop
- 🍁 Fall Festival | North Park Village Center
- 🍺 SAUCED Night Market | Half Acre Beer Co | Bowmanville
- 🎥 Chicago International Film Festival | Various locations
- 💀 Rosehill Cemetery ‘Crypt’ 5k Run/Walk | Ravenswood
- 🐶 Northalsted Halloween Pup Crawl | Halsdted and Aldine streets
- 👻 BooPalooza and BarkPalooza | Wicker Park
- 🛍️ Halloween Vintage and Artisan Market | Ravenswood Event Center
- 🚶 Walking Tour: Glitterati on the Gold Coast | Chicago History Museum | Lincoln Park
- 🇬🇷 Lincoln Square Greektober Fest | St. Demetrios
- 🏳️🌈 Downtown LGBTQIA+ Stories Walking Tour | 11 East Ida B. Wells Drive | Loop
- 🚌 Bus Tour: North by Northwest | Chicago History Museum | Lincoln Park
Sunday, Oct. 19
- 🍁 Fall Festival | North Park Village Center
- 🏠 Open House Chicago | Various locations
- 🇬🇷 Lincoln Square Greektober Fest | St. Demetrios
- 🎥 Chicago International Film Festival | Various locations
- 🎃 Roscoe Village Halloween Block Party | 2000 W. Roscoe St.
- 🛍️ Chicago Artisan Market | Morgan MFG | Fulton Market
- 💪 The Volunteer Fair | Royal Palms | Wicker Park
- 🐶 Howl-O-Ween Pet Fest | Bartelme (Mary) Park | West Loop
- 📚 Book Swap | Chinatown Branch
- 🎥 “Parents” | Music Box Theatre | Southport Corridor
- 🍻 Kolsch Service | Salt Shed Pub | Goose Island
- 🚶🏻♀️ Walking Tour: Hyde Park Murals | The Pepperland Apartments
- 🍊 “The Orange Eats Creeps” | Empty Bottle | Ukrainian Village
Chicago Fashion Week closes out Sunday — it was another stylish run, and I’m excited to see how the tradition grows. (This was only its second year.)

One of my favorite shows was Kone Ranger’s at Royal Palms Shuffleboard Club. You can check out their shop IRL in Avondale.
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