The Ultimate Guide to Fall Festivals for Chicago Families

Taste of Chicago, Pullman Park. Photo by Walter S. Mitchell III, City of Chicago
Taste of Chicago, Pullman Park. Photo by Walter S. Mitchell III, City of Chicago
8/31/25 - By Maureen Wilkey

Chicago is full of kid-friendly fall festivals, and many of them are FREE. From neighborhood Chicago harvest festivals honoring our diverse communities, like Lincoln Square Ravenswood Apple Fest or 79th Street Renaissance Festival, to kid-friendly fall festivals in Chicago that dig deep into our thriving food and art scenes, like the Lakeview East Festival of the Arts or Ravenswood Art Walk, there's a celebration happening every weekend from now 'til Thanksgiving.

Even Oktoberfest celebrations in Chicago, which might make you think of boozy crowds, make room for families with kids' zones and activities. And of course, there's Halloween and all the fun that comes with it.

Bookmark this long list of the best fall festivals in Chicago to do with kids. And get your calendar and your favorite fall sweater ready!

Tips for Visiting Fall Festivals with Kids

  • Go early to avoid crowds.
  • Check online for ticket and reservation requirements.
  • Bring an umbrella, bug spray, and sunscreen.
  • Figure out the best place to park.
  • Be ready for photo ops. 
  • Even for free festivals, bring cash for snacks and rides.

Frequently Asked Questions

Q: When do fall festivals in Chicago usually happen?

A: The earliest festivals in Chicago are over Labor Day weekend, with the last ones finishing around Thanksgiving.

Q: Are Chicago's festivals stroller-friendly?

A: Usually. You may need to check the terrain — street festivals are usually stroller-friendly while farms and county fairs might need a heavy duty wagon.

Q: Do I need to buy tickets in advance?

A: Always check the festival website. Many require advanced ticket purchases and sometimes even free festivals want you to make reservations in order to keep the crowds down.

 

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Places featured in this article:


Naperville Central High School

Downtown Downers Groveq

Various sites throughout Chicago

Logan Center for the Arts

Lincoln Avenue between Wrightwood and Webster

The Morton Arboretum