Fall in Chicago Bucket List

It seemed to come right out of nowhere (I blame cold and rainy June), but as the leaves on my driveway are telling me FALL HAS ARRIVED IN CHICAGOLAND! While I haven’t ordered my first PSL yet, that doesn’t mean that we can’t start compiling our Fall Bucket Lists. I have rounded up my family’s favorites, as well as some new events, because Fall is that beautiful time when we get a much needed respite from the humidity and old man winter hasn’t shown his ugly face yet. Grab your favorite plaid shirt and let’s tackle this Fall in Chicago Bucket List before all the Honeycrisp apples are gone!

Go Apple Picking

While June’s crazy weather has taken a few orchards out of the u-pick game this year, that doesn’t mean that there aren’t still great apple picking options for Chicagoans. Check out my favorite local apple picking farms before planning your next weekend and how to set up a caramel apple bar once you have brought your apples home!

Hunt for Fall Colors

Fall in Chicago shows you how beautiful it is to let things go. So let go of the electronics, your big and complicated plans and attempts to “Keep Up with the Joneses” and get outside. There are so many great paths for hiking and taking in the stunning Midwestern colors, from the Morton Arboretum to Starved Rock and so many gorgeous options in between.

Explore a No-Frills Farm

Looking for an authentic farm experience minus to pig races and extra frills? Then check out some of these independent and no-frills farms. Be sure to keep in mind that 2019 wrecked havoc on orchards so U-pick might be closed or extremely limited for this year.

Bear Down

So…let’s just forget about Thursday night’s game, ok? Because the Bears have a long season ahead of them and our future is oh so bright (hello, Khalil Mack!) and there are so many fun ways to watch the Bears game. Whether you are lucky enough to have Bears tickets (read my tips on visiting Soldier Field here) or getting together with friends to don navy and orange and chow down and scream at the television, Fall is the perfect time to be a Chicago Bears fan.

Play in a Corn Box

If you don’t end up with dried corn in your underwear after a Fall weekend are you REALLY a parent? Like seriously. Because no matter the Fall fest or farm, your kids are going to make a bee line for those massive corn boxes and you have no choice but to join in on all the fun. 

Plan a Fall Themed Photo Shoot

As I’m sure your Facebook feed will tell you, SO many photographers are scheduling photo shoots (if you ask me a mini-session is all you need!) for this Fall so if you have dreams of holiday cards filled with Fall foliage, book one of my favorite photographers ASAP.

Get Face to Face with a Scarecrow

Want to build your own scarecrow (but not at home—because honestly, who wants to deal with that mess?!?!) or simply check out other people’s creations? Then head to St. Charles for the 34thAnnual Scarecrow Fest

Cheer on a Pumpkin Eating Dinosaur

Pumpkin cannons are cool and all, but a pumpkin eating dinosaur that has smoke coming out of its nostrils? Now THAT’S  an amazingly unique way to celebrate Fall in Chicago. Read all about the quirky pumpkin experiences available to us Chicagoans here.

Enjoy a Moonlit Hayride

Love spooky stories and hayrides? Then head over to Pheasant Run in St. Charles for their moonlight hayrides. Not only is the wagon all decked out, but there are also delicious, Fall themed treats to enjoy.

Boo at the Zoo

You know that Halloween costume that your child changed his or her mind about at least fifteen times? Well, get your money’s worth out of it by attending all of the Boo at the Zoo activities held at both the Lincoln Park and Brookfield Zoos. Kids can trick or treat in their costumes while parents enjoy a brew or two. It’s the perfect Fall in Chicago combination. 

Check Out the Spookiest Houses in Chicagoland

One of the most fun (and free) ways to build up Halloween hype? Get some hot cider or chocolate and pile in the car to drive around and enjoy all of the different Halloween displays around Chicagoland. Whether you are looking for something gory and gruesome or inflatable fun, these houses in Chicagoland have it year after year.

Be Amazed by 1,000 Jack-o-Lanterns

Let me warn you—The Chicago Botanic Garden’s Night of 1,000 Jack-o-Lanterns will make you feel REALLY bad about your lame (and probably crooked) pumpkin carving. Seriously. The amazing artists behind the 1,000 jack-o-lanterns are so incredibly creating, showing off designs paying homage to all things Chicago and to cultural icons. It’s a beautiful event that is fun for the entire family and use these tips if you are interested in hosting your own pumpkin carving party.

Devour the Best Pies in Chicagoland

While there’s nothing better than grandma’s homemade pie, there are quite a few local pie shops that can give her a run for her money. My favorite Chicagoland pie shop? Bang Bang Pie and Biscuits. They even have pie classes so you can learn how to make your own decadent creation!

Give Back to the Chicagoland Community 

Don’t forget to take a break from all the family fun on your Fall in Chicago Bucket List and think about those who might be struggling this season. There are ample opportunities to get involved in bettering your community, and you can read about some of my favorite local organizations here.

By all means don’t let this list stress you out and make you think that you aren’t doing enough family-friendly fun this Fall. Instead, use it as a starting point to figuring out how you and your family want to spend those prized weekends when the weather is perfect and there are so many budget and family friendly activities to choose from. If all you manage to do is get a pumpkin from your local grocery store and watch “It’s the Great Pumpkin, Charlie Brown,” you are doing a great job.

Happy Fall, ya’ll!


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