It’s after Labor Day, which means for some of us it’s already fall while others are trying to hold on to summer. Host Jacoby Cochran, executive producer Simone Alicea, and Chicago artist Al Scorch discuss what they are looking forward to in September, including Chicagohenge, the Bears’ return, and pumpkin spice offerings. Plus, they’re watching some big news stories.

If you're new here, welcome! We’ve put together a starter pack for you, with episodes and articles to welcome you to the City Cast Chicago community.

For even more tips on how to make the most of September in Chicago, check out Hey Chicago’s take on what to do this month.

City Cast Chicago’s guide to September is made possible by our sponsors, Chicago Association of Realtors, Window Nation, and MUBI. City Cast Chicago is also powered by our members, who enjoy an ad-free version of the show. Find out more about how to become a member of City Cast Chicago.

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Chicago Public Schools has yet to place about 200 students with disabilities in classrooms, despite it being the second week of school. While the district says it is working quickly to place students in cluster programs, we ask Chalkbeat Chicago education reporter Samantha Smylie how families are managing this waiting period. Plus, Injustice Watch senior reporter Maya Dukmasova walks us through her investigation into a former UIC crime lab whose questionable forensic science led to multiple cannabis DUI convictions.  

Good News: Bad Butter, Lurker at Music Box, Workers Over Billionaires

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With the threat of the National Guard looming over the city, it’s important to remember immigration raids are still happening across Chicagoland. Host Jacoby Cochran talks with Diego Morales with the Pilsen Rapid Response Network about how organizers are responding and what Chicagoans should do if they encounter ICE operations.

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If you enjoyed today's interview with 2025 President of the Chicago Association of REALTORS®, Erika Villegas, learn more here.

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There’s still at least a few weeks left in patio season, which means there’s still time to meet some patio dogs. Bringing your dog to a restaurant patio or brewery has become a more common sight in Chicago, but what are the rules? City Cast contributor Leigh Giangreco talked with diners, dog owners, and restaurant workers in Roscoe Village to learn about pet etiquette at restaurants.

Good news: Respect The Mic, Art Therapy 

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President Donald Trump is reiterating threats to send National Guard troops to Chicago. A new report indicates they could come as soon as September. Host Jacoby Cochran and executive producer Simone Alicea discuss how local leaders are responding. Plus, they discuss the city’s progress (or lack thereof) on its Vision Zero goals, and they play Raddle, a new locally-grown puzzle that may replace your Wordle habit.

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In 2000, Chicago Mayor Richard M. Daley unveiled the “Plan for Transformation,” a decade-long initiative that demolished Chicago’s public highrises, overhauled the city's public housing system, and displaced thousands of Chicagoans. Author Natalie Moore and investigative reporter Mick Dumke have both covered the legacy of the Plan for Transformation and tracked the city’s claims about its overall success. We ask them both, how successful was the ‘Plan for Transformation, and how many of its lofty promises have gone unrealized to this day.  

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As Chicago Public Schools return for the 2025-2026 school year, major questions remain, like the future of the CPS budget gap, protections for immigrant students, and the relationship between the governor and district leaders. WBEZ Education reporter Sarah Karp and freelance journalist Brandon Pope are here to break down the pressing challenges facing CPS. Plus, the US attorney general increases threats towards Chicago, Chance drops his latest album Star Line, and we’ve got more pizza love to share.

Good News: Bulls Fest, Creative Mornings Chicago

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The city’s House Music Festival and Conference is back, which means it’s time for a dance break. We’re revisiting a conversation we had in 2022 with the co-hosts of WNUR’s Vintage House Show, DJ Lori Branch and archivist Lauren Lowery, about the roots of house music, the legacy of the now-landmarked Warehouse, and modern reinterpretations of the genre.

If you enjoyed today's interview with 2025 President of the Chicago Association of REALTORS®, Erika Villegas, learn more here.

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Steve Dolinsky made his name as ABC7’s “Hungry Hound” before retiring as NBC5’s “The Food Guy” earlier this year. This weekend, he’s bringing Pizza City Fest back to Chicago after a disastrous run two years ago. Dolinsky tells host Jacoby Cochran what’s new this year and hesitates to say if Chicago is still the country’s greatest pizza town. Plus, we get his takes on some other iconic Chicago foods.

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Heavy rain over the weekend left thousands without power while streets, highways and basements continued to deal with flooding. Host Jacoby Cochran and executive producer Simone Alicea discuss an effort to install new flood detection systems across the city. Plus, we’re covering the latest stadium news for the Fire and Bears, and exploring Chicago's coolest car collection. 

Good News: Chicago Sky and Chicago Stars 

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