We have known all year that regional transit agencies were headed towards a fiscal cliff, so it only makes sense that lawmakers finally passed a transit funding bill in the middle of the night last Friday. As the $1.5 billion package heads to the Governor’s desk, we’re looking at what made it in the final bill. Plus, we’re discussing where to find food support and free events around the city.

Good News: Coffee and Kamehameha Wave

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And just like that, it’s November. Producer Michelle Navarro is here with ways to help your neighbors. Executive producer Simone Alicea says now’s the time to learn to navigate the pedway. And host Jacoby Cochran is warning you to gear up for Christmas music.

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 November in Chicago, check out Hey Chicago’s take on what to do this month.

City Cast Chicago’s guide to November is made possible by our sponsors, The Newberry, Chicago Loop Alliance, Deborah's Place, and Chicago Board of Election Commissioners. 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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The loss of federal food assistance due to the government shutdown will affect nearly 2 million Illinoisans. Gov. JB Pritzker is directing $20 million to help close the gap, but Sun-Times reporter Tina Sfondeles explains that’s only a fraction of the need. She talks with executive producer Simone Alicea and Alex Nitkin with the Illinois Answers Project about what’s next. Plus, they discuss the charges facing local political candidates, transit funding, suburban tax loopholes, and a couple of architectural projects worth taking a look at. 

UPDATE: Early Friday, about an hour after this episode came out, state lawmakers passed a $1.5 billion transit bailout. Instead of some of the more controversial statewide taxes, money will come from the Road Fund and a localized sales tax increase. We'll have more next week. An earlier version of this episode's title has been changed to reflect the news.

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Since the beginning of  “Operation Midway Blitz,” Chicago neighborhoods have remained on high alert, afraid that immigration officials could arrest community members at any moment. This has made it especially difficult for people who work in public, such as construction workers, day laborers, and street vendors. Producer Michelle Navarro recently attended a street vendor crawl in Back of the Yards to talk with Chicagoans committed to shopping with and protecting those who remain most vulnerable to targeting by immigration officials.   

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Halloween is Friday, and for some of us, the best place to find a last-minute costume is one of the city’s vintage or thrift shops. And Chicago’s got no shortage of options, whether you’re looking for designer steals, great bargains, or selling your clothes. For Hey Chicago Newsletter editor Emmi Mack, this isn’t just a hobby but a way of life, as she grew up hanging out at vintage stores with her friends and working at the old Belmont Army Vintage. She joins host Jacoby Cochran with her guide to vintage shopping in Chicago.

Good News: Whistlemania 2

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Border Patrol Chief Greg Bovino has been ordered to testify in federal court this week as ICE continues to ignore court orders and tear gassed more Chicago neighborhoods over the weekend. Executive producer Simone Alicea and host Jacoby Cochran have the latest. Plus, Chicago’s number of tenant unions is growing as frustrations about renter protections and housing prices mount.  

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Three years ago, the first buses from Texas carrying migrants and asylum-seekers came to Chicago. More than 51,000 have arrived since then. With immigration agents now roaming the city, we’re checking in on where those new arrivals are now. Host Jacoby Cochran talks with Borderless magazine’s Mauricio Peña, Diane Bou Khalil, and Katrina Pham, along with Block Club Chicago’s Madison Savedra.

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While a ton of attention has been focused on the federal government shutdown and Chicago’s budget battle, south suburban Harvey is currently managing its own budget crisis and partial shutdown including layoffs and furloughs. Harvey World Herald founder Amethyst Davis is here to break down the latest. Plus, WBEZ’s Mariah Woelfel joins to discuss the fallout from ICE raids in Little Village and Cicero earlier this week. 

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At DePaul University, Chicago rapper Femdot is professor Femi Adigun for his course “Chicago Culture Through Hip Hop.” Today, class is in session as the artist sits down with host Jacoby Cochran to explore how Chicago’s history can be traced through rap music.

Good News: SUG N JAM Open Mic

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In honor of our 1,000th episode in March, we released a list of 1,000 things we love about Chicago. It includes not just things we at City Cast appreciate, but also things listeners, guests, and Chicagoans love most about the city. With Chicago once again squarely in the national spotlight, it felt like the perfect time to revisit this love letter to our city.

Nominate City Cast Chicago as Best Podcast and Hey Chicago as Best Email Newsletter in the Reader’s Best of 2025 under the City Life category.

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