Your Guide to October 2025 in Chicago

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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