Chicago Fall Day Trips Guide: Orchards, Festivals, and Family Getaways 2024

Is fall the best season? From pumpkin patches to Halloween fun, hay rides to apple picking, there are so many amazing things to do with kids in the fall.

In our Fall Fun Guide, local Chicago moms share their top tips and favorite spots for family outings, day trips, and family weekend getaways as the weather turns cooler.

Pumpkin picking is a firm fall favorite. Photo courtesy of Keller's Farmstand
Top things to do this fall in Chicago
Just about an hour from Chicago, kids can pick apples at Apple Holler from mid-August to November.
Apple Picking near Chicago: Best Apple Orchards for Apple Picking with Kids
Taste of Chicago, Pullman Park. Photo by Walter S. Mitchell III, City of Chicago
Best Harvest & Pumpkin Festivals in Chicago for Fall Family Fun
Gobbert's Farm photo by Ryan Dickey via Flickr 2.0
Best Pumpkin Patches Near Chicago for Families
Hanging out in Galena. Photo by Maureen Wilkey
20 Fall Day Trips from Chicago for Families
Shimmy your way through Chicago SummerDance! Photo courtesy of the Chicago Department of Cultural Affairs
Best Free Things To Do in Chicago This Fall With Kids
It's apple season! Photo courtesy of Apple Holler Orchard
Fall Bucket List for Kids: 37 Things To Do in Chicago This Fall

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