30 Best Things to Do in Chicago October 2025 with Kids, According to Mommy Poppins Editors

St. Charles Scarecrow Festival.
St. Charles Scarecrow Festival.
9/28/25 - By Maureen Wilkey

Halloween is always exciting, and October in Chicago is delivering a whole lot of treats: We have apples and pumpkins to pick; kids can enjoy stars, stories, and s'mores in Thatcher Woods or join a super hero run in Villa Park. Kids can also see new plays at Chicago Children's Theater or the Stahl Family Theatre.

Of course, we’ve also covered you for Halloween events in Chicago. If you'd rather trick-or-treat at businesses than at houses or apartments, visit Lincoln Square, Ravenswood, or Lincoln Park, or trick-or-treat with the animals at Brookfield's Boo at the Zoo. And if you're more comfortable staying in for the holiday, we have some fun Halloween games to recommend!

Check out our full line-up of favorite fall festivals here, or read on to see the best of October!

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Places featured in this article:


Easter Seals DuPage and Fox Valley

America's Antique Mall Algonquin

Centennial Recreational Center

Lincoln Avenue between Wrightwood and Webster