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City Cast Chicago

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?

If so, please consider nominating Hey Chicago for the Reader’s Best of Chicago awards! All you have to do is follow this link, and type in “Hey Chicago” … it will prompt you to create an account, but it’s very quick, I promise!

You can also nominate our dynamic daily podcast City Cast Chicago under the podcast category.

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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]

Podcast Player: "ICE Tears Gasses Neighborhoods, CTA Fare Hike, and Goodbye The Promontory"

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 🎧]

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."

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Your Chicago News Quiz

No Kings protest
June’s No Kings protest brought thousands to the streets downtown. Another No Kings protest is scheduled for tomorrow at noon. (Emmi Mack / Hey Chicago)

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.

Have you been paying attention?

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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.

Spooky bracket
What's scarier — Lower Wacker or a multiway intersection?

What To Do

Friday, Oct. 17

Saturday, Oct. 18

Sunday, Oct. 19

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.)

Kone Ranger
Kone Ranger’s 2025 collection, presented atop a shuffleboard court in Wicker Park. (Courtesy of Cori Dahl)

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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