The top fall family activities in Chicago

Written by: Amanda Simkin

Fall family activities in Chicagoland

It’s that time of year when there is pumpkin-flavored EVERYTHING and the weather is absolutely perfect for exploring before old man winter comes and sends us all into a seasonal depression (c’mon, I know I’m not the only one who goes crazy being cooped up inside with energetic little ones, right?!?!).

So make the most out of fall in Chicagoland and create your own family fall bucket list. Need some inspiration? Here’s what is on ours—and be sure to keep up with our autumnal activities over on Instagram, too!

Go apple picking.

Go on a nature walk to admire the fall colors.

Rake leaves…and of course jump into them!

Head to a local pumpkin farm and pick your own pumpkin.

Throw a pumpkin carving party.

Celebrate Oktoberfest at some of these family-friendly celebrations.

Drive around Chicagoland to visit some of the absolute best decorations and homes that are decked out for Halloween.

Cheer on the Cubs on their way to a World Series victory!

Take part in the biggest jack-o-lantern display in the Midwest!

Have a big family bonfire…with s’mores, of course!

Check out some of the many family friendly fall fests going on around Chicagoland.

Pop some popcorn and watch It’s the Great Pumpkin, Charlie Brown.

Bake pumpkin chocolate chip cookies.

Collect colorful leaves and make some crafts from them (paper plate, scissors, glue and you have the perfect fall leaf wreath).

Go on a search for the best pie in Chicagoland. Don’t know where to start? Check these out!

Happy fall, y’all!


Amanda Simkin, a lifelong Chicagoan, created her blog ( to share how she celebrates motherhood in Chicago. She offers “insider’s guides” for both well-known and off-the-beaten-path family-friendly gems. Her fans include Red Tricycle Chicago and Chicago Parent Magazine.


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Posted on October 03, 2016 at 9:54 AM