Your Guide to September 2025 in Chicago

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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