
City Cast Chicago
😢 A sad Bryn Mawr birthday bash
May 29, 2026 · — Emmi Mack
Calling all freaks! Misfits and weirdos too. The owner of The Alley is looking for a successor. Think you got what it takes to keep the goth cornerstone thriving for another 50 years? Pitch yourself at the Alley’s upcoming block party.
It should be quite a celebration — unlike the somber block party I just attended on Bryn Mawr. More on that bash below 👇👇👇

What's CITY Talking About
Regulation For AI in Illinois
Gov. JB Pritzker said he will sign off on plans to build a regulatory framework for Illinois regarding artificial intelligence. The bill, which will make Illinois the first state to require independent safety audits for AI developers, passed the state House and Senate nearly unanimously. AI companies also backed the bill. [Tribune 🔒]
School Board Hopefuls File Election Petitions
This year, for the first time, Chicago will fully elect its school board. On today’s podcast, we talk about the 51 candidates who petitioned to get on the ballot. Plus, traffic court confusion is hurting immigrants, and Munetaka Murakami’s homers are fueling the White Sox. [City Cast Chicago 🎧]
Pope and Mayor Meetup
Mayor Brandon Johnson said he and Pope Leo XIV discussed “the brutal legacy of slavery,” City Council’s vote to cease fire in Gaza, war, and affordability. Johnson also invited the pope to give mass at Grant Park in 2027. [Sun-Times]
- Taking a stand: The pope issued a warning on AI. [City Cast Chicago 🎧]
Riot Fest Drops Lineup
The fest, which returns to Douglass Park Sept. 18-20, announced their lineup with performances from Tool, Twenty One Pilots, Pierce the Veil, Alanis Morissette, and more. Tickets are on sale now. [Riot Fest]
- Also: Lolla aftershows tix are live. [Do312]
Sponsored Content

The Middle of Everything
Ever notice how the best part of anything is right in the middle? Come see for yourself in Illinois, where you can hit the trails in breathtaking state parks. Experience classic Americana on Route 66. And even kayak through a glistening canyon of skyscrapers. It’s all right here in Illinois.
Sponsored Content

30 Years of Great Nights Out
North Shore Center for the Performing Arts in Skokie celebrates 30 years of unforgettable performances. Plan your next night out with Michael Carbonaro (July 18), Maz Jobrani (July 19), Chris Botti (July 26), Ghostbusters in Concert (Oct. 7–8), and Maria Bamford (Oct. 24. Free parking, easy CTA access, and something for everyone. Get tickets on Ticketmaster.com.

What To Do
Friday, May 29
- 🌭 Windy City Hot Dog Fest | Six Corners | Portage Park
- 🎵 Do Division | Division between Damen and Leavitt | West Town
- 🇩🇪 Maifest | Lincoln and Western | Lincoln Square
Saturday, May 30
- 🪁 Kite Festival | Douglass Park
- 🔨 Tool Library Repair Fair | Chicago Tool Library | Garfield Park | Free
- 🎵 House Music is Home | Navy Pier | Free
Sunday, May 31
- 🛍️ SummerSalt Market | Salt Shed | Goose Island | Free
- ⚾️ Sox vs. Tigers Family Sunday | Sox Park | Bridgeport
- 🎭 "GIRLS, GIRLS, GIRLS!” opens | Rivendell Theatre Ensemble | Edgewater
And Neighbors: Don’t forget to RSVP to our live podcast taping at Switchyards on June 4.
Free · Daily

