Chicago Fall Day Trips Guide: Orchards, Festivals, and Family Getaways 2025

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.

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
The Ultimate Guide to Fall Festivals for Chicago Families
Try a Fall outing to one of these great pumpkin patches near Chicago. 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
It's apple season! Photo courtesy of Apple Holler Orchard
Fall Bucket List for Kids: 37 Things To Do in Chicago This Fall
Have some fall fun at these corn mazes near Chicago. Photo courtesy of All Seasons Orchard in Woodstock, Illinois.
Amazing Corn Mazes Near Chicago for Kids

OUR LATEST VIDEOS

Latest Fall Activities News

Watch the Macy's Thanksgiving Parade. Photo courtesy of the Macy's Thanksgiving Day Parade
Thanksgiving, Pumpkin Destruction Day, and More Holidays & Activities for November 2025
From pickles to freckles to Monopoly - plus Thanksgiving!
READ MORE
Take a picture in front of the famous pumpkin wall at Nalls Produce! Photo courtesy of the author
Pumpkin Hill at Nalls Produce: A FREE Hidden Gem for Fall Family Fun Near DC
Pumpkin Hill at Nalls Produce packs plenty of free fall fun!
READ MORE
National Zoo's Boo at the Zoo is one of the DC area's most popular Halloween events. Photo by Juan-Carlos Briceno, Smithsonian’s National Zoo and Conservation Biology Institute
Best Halloween Events in DC 2025 for Kids and Families: Halloween Festivals, Trunk-or-Treats, and More
We've rounded up the best 2025 Halloween events for kids and families in the Washington, DC area.
READ MORE
It's not fall without a visit to the pumpkin patch. Photo courtesy of Great Country Farms
Fall Bucket List for Kids: 31 Top Things To Do Near DC This Fall
We've got the ultimate fall bucket list for DC families!
READ MORE
Pick the perfect pumpkin at Great Country Farms.
Best Pumpkin Patches Near DC for Picking the Perfect Pumpkin
Pick the perfect pumpkin at one of these local farms and pumpkin patches.
READ MORE
There's lots of farm fun to be had at Great Country Farms! Photo courtesy of Great Country Farms
The Perfect Weekend Itinerary for a Loudoun County, VA Fall Getaway
Soak up the autumn vibes in Loudoun County this fall.
READ MORE
Load more