
City Cast Chicago
🫦 Will Bears succumb to Hoosier temptation?
January 30, 2026 · — Emmi Mack
Hey Indiana! That got your attention, didn’t it? Well, it’s what our beloved Bears could be saying soon. The Indiana state senate approved a bill that would fund a potential stadium … but wait … SHOULD the Bears move to Indiana?
Now, onto the news and your weekly quiz!

What's CITY Talking About
Ex-Cop Who Murdered Sonya Massey Gets 20 Years
Sean Grayson, the former sheriff’s deputy who shot and killed Sonya Massey in 2024 was sentenced to 20 years in prison. Massey had called 911 over a suspected prowler outside her Springfield home, and Grayson was the responding officer. He was convicted of second-degree murder in October. [Tribune 🔒]
Bad News on the Weather Front
Despite hopes for a sudden warm-up, it looks like this weekend will be extra frigid. With wind chill, it’ll still feel below-zero outside … and more snow is on the way. [Block Club]
- Wait: But is it a polar vortex? [Hey Chicago 💻]

Chicago’s LGBTQ+ Affairs and Parking Meter Negotiations
After calls to better protect Chicago’s LGBTQ+ community, Mayor Johnson has officially announced Antonio King as the new Director of LGBTQ+ Affairs. We discuss the hire on today’s episode of City Cast Chicago, along with Windy City Times’ Jake Wittich and Crain’s Chicago’s Justin Laurence. Also discussed: Greg Bovino’s demotion, closed-door parking meter negotiations, and Benny the Bull. [City Cast Chicago 🎧]

This Week’s Must-Read
“Remind me … Why do we go other places?” columnist Neil Steinberg says of Psistaria Taverna in Lincolnwood. I have actually uttered these exact words while at Psistaria, my family’s go-to Greek restaurant. Steinberg also shouts out the eternally affordable Pita Inn: another suburban fave. [Sun-Times]
- My Psistaria order for the table: Taramosalata (ask for extra sesame bread), gigantes, dolmades, saganaki (obviously), Chef George’s salad, fried zucchini, peas (yes, peas), and a gyros appetizer. Thank me later.

Your Chicago News Quiz

In this week, full of national unrest, the headlines kept coming. Were you paying attention?
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Theatre Week is back! Feb. 5 - 15
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What To Do
Friday, Jan. 30
- 🤠 "My Life as a Cowboy" | Open Space Arts | Uptown
- ⚾️ SoxFest | Ramova Theatre | Bridgeport
- 🎷 Indigenous Jazz Ensemble | Logan Center for the Arts | Woodlawn
- 🎤 Karaoke | Empty Bottle | Ukrainian Village
- 🍽️ Chicago Restaurant Week | Various locations
- 💸 Free admission | Chicago History Museum | Lincoln Park
- 🎶 Jessie J | House of Blues | Loop
- 🎭 Chicago International Puppet Theater Fest | Various locations
Saturday, Jan. 31
- ⚾️ SoxFest | Ramova Theatre | Bridgeport
- 🍺 Cider Summit Chicago | Navy Pier
- 🍎 Indoor Farmers Market | 2800 N. Milwaukee Ave. | Logan Square
- 🎶 Vinyl Vibe Selectors | Nighthawk | Albany Park
- 🛍️ Edgewater Indoor Market | Broadway Armory
- 🍎 Green City Indoor Market | 3057 N. Rockwell St. | Avondale
- 🛍️ Ravenswood Makers Market | KOVAL Distillery
- 🍽️ Chicago Restaurant Week | Various locations
- 🍎 Winter Farmers Market | Roosevelt Collection Shops | South Loop
- 🛍️ Vintage House Market | Rockwell On the River | Avondale
- 🍽️ James Beard Foundation benefit | The Abbey | Lake Geneva
- 🎭 Chicago International Puppet Theater Fest | Various locations
- 🎶 House Calls | Thalia Hall | Pilsen
- 😎 ECLIPSE 4.0 | Epiphany Center for the Arts | West Loop
- 🎤 Patti LuPone | The Auditorium | Loop
Sunday, Feb. 1
- 🎭 “Trial in the Delta: The Murder of Emmett Till“ | Kimball Arts Center | Humboldt Park
- 🍻 Reverberation | Revolution Brewing | Avondale
- 🛍️ Vintage House Market | Rockwell On the River | Avondale
- 🎭 "rustbelt." closing | Facility Theatre | Humboldt Park
- 🍽️ Chicago Restaurant Week | Various locations
- 🛍️ Sanctum Market Winter Edition | Hoste | Pilsen
- 🚲 2nd Anniversary Sale and Party | Igor Does My Bike | Edgewater
- 🎭 Chicago International Puppet Theater Fest ends | Various locations
- 🎤 Black Voices in Cabaret | DuSable Museum | Washington Park
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☝️ Also, need a last-minute gift for someone? Or just a personal pick-me-up? Hit up these kitschy Chicago vending machines. You won’t find a Snickers bar, but you can find CTA souvenirs.
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