
City Cast Chicago
🧐 CPS superintendent vs. CEO
May 19, 2025 · — Emmi Mack
Calling all alleycats! Alleys are the backbone of Chicago. They structure our shortcuts. They house our secondhand steals. They’re where teenagers rendezvous. They’re where you used to buy weed. They’re the reason that, unlike New York, the city doesn’t stink like garbage in the summer.
🐈 On today’s podcast, we’re talking alleys. We’ve also got your regular roundup of Chicago news.


What Chicago's Talking About

CTU Reelects Stacy Davis Gates President
Stacy Davis Gates will continue leading the Chicago Teachers Union. Chicago teachers voted Friday to retain Davis Gates as president. She’s been president since 2022 and recently oversaw the finalizing of the CTU’s new contract. With a 64% majority, her win represents support for the union’s social justice platform. [WBEZ]
Illinois Is Last State Without Property Tax Foreclosure Reform
Two years ago, the U.S. Supreme Court ruled it’s unconstitutional to take all of someone’s home equity over unpaid property taxes. The practice mostly affects Black communities. Today, Illinois is the only state that hasn’t adopted reforms to give those who lose their homes their fair share of the tax sale proceeds. [Sun-Times]
Chicago Returns Mayan Frieze to Mexico
The National Museum of Mexican Art in Pilsen is returning an ancient Mayan frieze to Mexico. The limestone frieze is legal to own, but the museum said it’s taking an “ethical stance” in repatriating the piece. It was made sometime between 500 to 900 C.E., during the Classic Period of the Mayan civilization. [WTTW]
Pope’s Old House Up for Auction
The Dolton home where Pope Leo XIV grew up will go to the highest bidder. The three-bedroom house was on the market for $199,000 when news broke that Chicagoland’s own Robert Prevost was the new pope. Naturally, the homeowner yanked it off the market — temporarily. It goes up for auction June 18. [Crain’s 🔒]
- Related: Take a closer look at the pope’s old house. [City Cast Chicago 🤳]
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What To Do
Monday, May 19
- 🏛️ Chicago Preservation Expo | 4-8 p.m. | Free | Loop
- 👻 Ice Nine Kills: Silver Scream-a-Thon | 6 p.m. | $69.62+ | Uptown
- 🍽️ Family Dinner Improv Show | 6:30-8 p.m. | $19.72 | Edgewater
- 🖼️ Gala LXIV | 6:30-9 p.m. | $44.52+ | Logan Square
- ⚾️ White Sox vs. Mariners | 6:40 p.m. | $16.25+ | Rate Field
- 🎤 the corner | 7 p.m. | $13.95 | Hyde Park
- 🤣 Elder Gay: a comedy showcase | 7 p.m. | $16.24 | Humboldt Park
- 🕺🏻 Free Mondays | 9 p.m. | Free | Ukrainian Village
Tuesday, May 20
- 🍎 Division Street Farmers Market | 7 a.m. to Noon | Free | Gold Coast
- 🖼️ Free Tuesday at the MCA | 10 a.m. to 9 p.m. | Free | Streeterville
- 🎨 Mosaic Art Making | 1-6 p.m. | $44.52 | Bronzeville
- 🎉 Singles Party | 5-8 p.m. | $25 | West Town
- 👟 The Final Stretch Shakeout with Nike and Peacerunners | 6:30-8 p.m. | Free | Garfield Park
- 💕 Meet IRL | Curated Speed Dating | 6:30-9 p.m. | $39.26 | Near West Side
- 🎷 Jimmy Bennington Colour and Sound | 6:30-8:30 p.m. | $16.58 | Edgewater
- 🎤 Open Mic | 7 p.m. | Free | Lakeview
- 🍅 Tomato Throw Show | 7:30-9 p.m. | $29.50 | Streeterville
- 🍕 Paulie Gee Q&A + Book Signing | 7:30-9 p.m. | $29.50 | Wicker Park
- 🤣 Open Stage | 9:30 p.m. | Free | Lakeview
😘 Till tomorrow, Chicago!
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