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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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.

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Your Guide to October 2025 in Chicago