Despite President Donald Trump calling the city a “hellhole,” Chicago was named Best Big City in the country by Condé Nast Traveler for the ninth year in a row. Host Jacoby Cochran sat down with Choose Chicago’s CEO and president, Kristen Reynolds, to discuss what it’s like to market our city to tourists, particularly in a time when Chicago is constantly in the national spotlight. 

Good News: Destinos Chicago International Latino Theater Festival

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Lawsuits against the Trump administration are coming down left and right in Chicago, leading to blocks against National Guard deployment and orders that ICE can’t tear-gas journalists and peaceful protesters. But the president has shown he’s looking to get around the law in any way he can, which has us wondering: Do these lawsuits even matter? Host Jacoby Cochran talks with ACLU-Illinois’ Ed Yohnka about the efficacy of legal challenges and how to put their know-your-rights guides into practice.

Good News: Chicago International Film Festival

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A judge has temporarily blocked National Guard deployment in Chicago. This comes as a federal judge ruled against ICE’s arrest tactics. We’re breaking down the latest updates with executive producer Simone Alicea and The Triibe’s Corli Jay. Plus, state lawmakers are back for the fall veto session next week, Bears seek Hail Mary redemption in DC, and Chatham welcomes a new wine bar to 75th street. 

Good News: Slow and Low Lowrider Festival

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Think you already know the best restaurants in Chicago? What about the ones that operate inside other establishments? Chicago’s pop-up scene is legendary, but hard to track if you’re not in the know. That’s why host Jacoby Cochran is talking with Infatuation Chicago’s John Ringor, who’s been tracking pop-ups all summer.

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With all the focus on what the feds are doing in Chicago, let’s remember there are still local stories unfolding. Neighbors have been pushing for more information about what will happen to Ford City Mall on the Southwest Side. Bridge Industrial is seeking to buy the property to turn it into an industrial corridor. Host Jacoby Cochran talks with the Sun-Times Lee Bey and Block Club’s Atavia Reed about the plans for the mall, the businesses that are still there, and what they’ll miss about this legendary third space.

Nominate us for the Reader’s “Best of Chicago” for “Best Podcast” and Hey Chicago for “Best Email Newsletter”

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The Trump administration has announced it’s withholding $2.1 billion in federal funds for Chicago transit projects, including the extension of the Red Line. The extension has been decades in the making. While local officials grapple with the future of the project, we’re revisiting a conversation we had in 2023, when it finally seemed like it was really happening. CTA’s TaNesheha Marshall and Andrea Reed with the Greater Roseland Chamber of Commerce explain why many on the Far South Side have pushed for the extension.

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The White House confirmed it’s authorizing the deployment of 300 National Guard troops to Illinois against the wishes of Gov. JB Pritzker. The announcement came hours after a woman was shot and injured by immigration agents in Brighton Park. Host Jacoby Cochran and executive producer Simone Alicea break down what we know so far.

Resources mentioned:

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The federal government’s rhetoric and tactics have only intensified around Chicago since border patrol agents marched along Michigan Avenue over the weekend. The president again threatened to send the military to Chicago, and protesters in Broadview are facing charges. Executive producer Simone Alicea is going through it with Axios Chicago’s Justin Kaufmann and Block Club’s Melody Mercado. They also discuss a plan for the future of downtown, the Bears seeking taxpayer money for a stadium in Arlington Heights, Bad Bunny in the Super Bowl, and Justin’s sketch comedy troupe.

Here’s the link to send any recordings of federal agents in Chicago to local journalists.

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With spooky season officially here, we’re getting into the spirit by holding a tournament for the scariest things in Chicago. From haunted hotels to thrilling intersections to Chicago’s underworld (aka lower Wacker), the City Cast Chicago team will crown a winner. Disagree with our picks? Vote in the first round and prove us wrong.

Good News: Beyond the Screen

What’s not scary? Becoming a City Cast Chicago Neighbor! You’ll enjoy perks like ad-free listening, invitations to members only events and more. Join now at https://membership.citycast.fm/ 

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October marks the holiday sprint to the end of the year. Hey Chicago newsletter editor Emmi Mack has everything you need for Halloween. Executive producer Simone Alicea has fall fun for the scaredy cats. And host Jacoby Cochran is reminding you to watch for street sweeping. 

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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 Architecture Center, Window Nation, Steppenwolf Theatre, TimeLine, and City Cast Neighbors (Through Oct. 3, when you sign up, you get this awesome tote that says “Neighbors Make Chicago”). 

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