
City Cast Chicago
🏢 Schools for sale in Chicago
May 16, 2025 · — Emmi Mack
Happy Friday, Chicago! Between Mayfest and Margarita Fest, there’s lots to do in the city this weekend. But remember to donate at the gate! I’m not trying to be a narc, but Chicago street fests are struggling.
🍺 Do your part before having a giant beer!

What Chicago's Talking About

20 Closed Chicago Schools for Sale
Twenty former CPS buildings are currently up for bid, with the hope of bringing $8.2 million to the city. Most of the buildings have sat empty since the 2013 mass school closures under then-Mayor Rahm Emanuel. The district currently spends at least $2 million annually to maintain the sites. [Chalkbeat]
- Related: How did closing 50 schools change Chicago? [City Cast Chicago 🎧]

Mayor Johnson’s First Two Years in Review
Halfway through Mayor Brandon Johnson’s first term, Block Club Chicago’s Rachel Hinton discusses the administration's highs and lows. Tribune sportswriter Julia Poe also joins to talk Chicago Sky: offseason moves, playoff hopes, and union negotiations. All that and more on today’s podcast. [City Cast Chicago 🎧]
Will Lawmakers Address CTA Budget Gap?
As the transit system’s $771 million fiscal cliff approaches, state Sen. Ram Villivalam teased legislation that may actually pass before the May 31 deadline. Villivalam said the General Assembly’s current proposal centralizes power to “a main authority” and calls for the creation of a CTA police force. [Crain’s]
- Related: What might a centralized transit authority look like? [City Cast Chicago 💻]
This Week’s Must-Listen
Ever wonder why you can’t build a nuclear bomb in Chicago? Not really? Regardless, a new Curious City episode explores the interesting roots behind a seemingly obvious Illinois law. Its origins trace back to widespread protests against nuclear armament during the 1980s. [WBEZ]

Take This Week's News Quiz

Popemania, Chicago school board drama, and changes at City Council … it was a busy week in Chicago news. Were you paying attention?
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What To Do
Friday, May 16
- ✍️ Generative Poetry Workshop | Noon to 2 p.m. | Free | Near North Side
- ⚾️ Crosstown Classic | 1:20 p.m. | $76.16+ | Wrigleyville
- 🍺 Mayfest | 4-10 p.m. | Free | Lincoln Park
- 🍹 Windy City Margarita Fest | 5-10 p.m. | $5 suggested | Pilsen
- 🎵 La Cantera | 7-9 p.m. | $5 | Humboldt Park
- 💥 ‘80s Prom | 8:30 p.m. | $55.20 | Lincoln Park
- 💪 Borderless House Party | 7:30-9:30 p.m. | $35+ | Buena Park
- 🎤 Central Cee | 8 p.m. | $68.88 | Uptown
- 🎵 Lettuce + GZA | 8 p.m. | $52.96 | Bridgeport
- 🕺🏻 Silent Party | 10 p.m. | $13.95+ | Hyde Park
Saturday, May 17
- 🧵 Craft Fair | 10 a.m. to 6 p.m. | Free | Roscoe Village
- 🍺 Mayfest | Noon to 10 p.m. | Free | Lincoln Park
- 🍹 Windy City Margarita Fest | Noon to 10 p.m. | $5 suggested | Pilsen
- ⚾️ Crosstown Classic | 1:20 p.m. | $91.37+ | Wrigleyville
- 🎉 AANHPI Forward | 2-7 p.m. | Free | Uptown
- 🎶 Peter Bjorn and John | 8 p.m. | $30 | Pilsen
- 🕺🏻 Tame Impala Dance Party | 9 p.m. | $27.98 | Wicker Park
- 🎵 Porter Robinson + DJ Set | 11 p.m. | $43.37+ | Bridgeport
- 🎶 Afro Fusion Saturday | 11 p.m. to 5 a.m. | Free-$55.20 | Uptown
Sunday, May 18
- 🍒 Northwest Farmer Market | 9:30 a.m. to 1:30 p.m. | Free | Mayfair
- 🍎 North Park Community Farmers Market | 10 a.m. to 2 p.m. | Free | North Park
- 🧵 Craft Fair | 10 a.m. to 6 p.m. | Free | Roscoe Village
- 📿 Hyde Park Handmade Bazaar | 11 a.m. to 3 p.m. | Free | Hyde Park
- 🍹 Windy City Margarita Fest | Noon to 10 p.m. | $5 suggested | Pilsen
- ⚾️ Crosstown Classic | 1:20 p.m. | $71.83+ | Wrigleyville
- 🎵 Upbeat | 12:45-2 p.m. | Free | Lincoln Park
- 🍺 Mayfest | 12-9 p.m. | Free | Lincoln Park
- 🎲 Bingo | 7-9 p.m. | Free | Humboldt Park
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Navy Pier: Where fun is always in the forecast
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One more thing: The city has added 11 new speed cameras. Check the locations. Remember them. You’ve been warned.
By the way, if you saw an email from our advertiser Williamstown Theatre Festival addressing Hey DC … don't worry, it was actually meant for you, just in case you're interested in traveling for theater this summer.
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