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Fun Things to Do This Fall in Chicago and Illinois

There’s nothing quite like fall in the Midwest. The leaves change to beautiful hues, there’s a chill in the air, and the weather causes residents to head outside and celebrate all of the fall activities in Chicago. We’ve put together some of our favorite things to do in Chicago in the fall in hopes of getting you out of the house and enjoying warm cider and apple doughnuts in no time. Don’t miss these fun things to do in fall in Chicago and Illinois.

Fun Fall Activities in Chicago and Illinois-Kids Are A Trip

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What to do in Chicago with kids this fall

1. Visit the world’s largest corn maze in Illinois

About an hour and a half north of Chicago and just south of the Wisconsin border is Richardson Adventure Farm, home of the world’s largest corn maze. This farm is more than a maze. There is a petting zoo, giant slides, bounce pillows, ORB rides (picture yourself inside a giant ball rolling down a hill), a zip line, train, and fudge shop.

Richardson’s is an intricately designed masterpiece. A lot of work goes into the maze’s design each year, ensuring people have many exits along the way and no dead ends. Everyone has a map and there are checkpoints to find throughout the maze.

Explore Richardson Corn Maze Fall Activity-Kids Are A Trip

Finding all of them can take a couple of hours, but if you find a minimum number of checkpoints you can earn a completion certificate. This is one fall family activity not to be missed!

Another corn maze in Chicago is Hardy’s Reindeer Ranch in Rantoul (near Champaign) where visitors will find a ten acre corn maze to explore. There’s also a pumpkin launching cannon, hay rides, pedal cars, and reindeer tours too. Yes, there are reindeer here! It’s definitely a fun day out!

2. Take a fall hike in Illinois

Chicago has an abundance of parks, hiking trails, and Lake Michigan beachfront perfect for exploring on a beautiful fall day. One of our favorite hikes is Starved Rock State Park in Utica, Illinois, especially when the leaves start to change colors.

The park has over 18 canyons carved by snow runoff and natural springs, creating a breathtaking landscape. There are over thirteen miles of well-marked trails for families to explore, and it makes for a perfect day trip from Chicago.

In southern Illinois, a visit to Shawnee National Forest to explore Garden of the Gods wilderness area and Cave-in-Rock State Park shouldn’t be missed. Cave-in-Rock is a 55 foot wide cave overlooking the Ohio River and it is the perfect spot for hiking, picnics, and fishing.

Starved Rock State Park Illinois fall-Kids Are A Trip
Starved Rock State Park in fall Photo: Creative Commons

Adventurous souls will want to head to Shawnee Bluffs Canopy Tour, Illinois’ first tree-based, eco-friendly zip line. The course consists of eight zip lines and three aerial suspension bridges, providing spectacular close up views of fall foliage in Illinois.

Where to Stay in Chicago with Kids

Visit the city of Galena and see the changing leaves from above on a hot air balloon ride. Galena On The Fly offers hot air balloon rides from sunrise to sunset, year-round. While in the air, families have 360-degree views over three different states. After landing, explore the town of Galena with its charming shops, art galleries, and historic sites.

3. Visit a U pick apple orchard

One of our favorite things to do in the fall is picking apples at one of the local orchards. Finding the best apples is an annual event in our house and one of our favorite places to go is Apple Holler in Wisconsin. The reason we travel so far is because they consistently have a large selection of apples available and after 13 years of visiting, it is officially a tradition.

There are plenty of other apple orchards in Chicago and the suburbs. You can find an apple orchard near you at PickYourOwn.org. Don’t miss our tips for visiting apple orchards in Illinois where you can find some great apple recipes too!

Apple Orchard apples in crate - Kids Are A Trip

4. Check out one of the awesome fall festivals in Illinois

Fall means festival time in Illinois and there are plenty of things to do in Chicago and around the state all season long. Most Chicago fall events begin in September and continue through the end of October. Some of the favorites include:

The Morton Arboretum

Enjoy fall at the Morton Arboretum with a variety of events. There’s a scarecrow trail around Meadow Lake, the Fall Color 5K, and other activities every day in October. Special events include the Fall Cider and Ale Festival, Meet the Beekeeper, Boo Breakfast, Family Jack O’Lantern Hikes, and more!

Naperville Oktoberfest: September 30 – October 1

If you’re looking for Oktoberfest in Chicago, don’t miss this one hosted by Naper Settlement. The event features pumpkin carving, polka bands, pretzel eating competitions and more. It’s the perfect excuse to put on your dirndl and lederhosen and celebrate the fall season German style! Prost!

Oktoberfest Chicago Accordion Naperville
Photo courtesy of City of Naperville

The Great Highwood Pumpkin Festival – October 7-9

The city of Highwood celebrates the 10th annual Great Highwood Pumpkin Festival with a pumpkin festival to rival all others. This year they support the Make-A-Wish of Illinois and will attempt to beat the Guinness World Record for the most lit jack-o-lanterns in one place!

There are also costume contests, a pumpkin parade, carnival rides, entertainment, and food. Fun times for everyone with the big pumpkin lighting on Sunday night.

Chicago Botanic Garden Fall Fun

The Chicago Botanic Garden in Glencoe has fabulous fall events. Check their site to see what’s happening this fall.

There are many other festivals not to be missed around the state, so check out the Enjoy Illinois page for additional ideas!

5. Take a drive to see the leaves change color

Before heading out for a drive to see changing leaves, check a fall foliage map so you know you will be guaranteed to see color.

15 Fun Things to Do in Chicago in the Winter with Kids

Some of our favorite routes to drive for leaf peeping include the Illinois River Road, Chicago to Lake Geneva, along the shore of Lake Michigan, the Great River Road along the state’s western edge, or heading north to Door County, Wisconsin.

If you visit these destinations at the right time, you will not be disappointed by the spectacular hues you will find! And if you’re looking to go further afield, don’t miss these fabulous Midwest fall drives

Door County Wisconsin fall leaves changing road
Photo: Unsplash

6. Find a pumpkin patch near Chicago

There are pumpkin patches all over the Chicago area, because Illinois grows more pumpkins than any other state. Those on the hunt for good carving pumpkins shouldn’t have to drive very far. Check before heading out as some have certain days and times they are open. Here are some of our favorite places to go picking:

Goebbert’s in Hampshire, IL – Located northwest of Chicago, this family farm has a fall festival, u pick pumpkin farm, petting farm, and a pumpkin eating dinosaur. Can you say awesome!

Stade’s Farm and Market in McHenry, IL – Just south of the Wisconsin border this pumpkin farm has u pick pumpkins and plenty of activities for a day out. There are farm-tractions including a carousel, tractor tire pyramid, and duck races for 8 weeks through the fall, during their Shades of Autumn Festival. Kids will never say they are bored!

Bengtson’s Pumpkin Farm in Homer Glen, IL – In addition to gathering pumpkins, the farm has pumpkin fest from September 16th through the end of October. Kids can watch pumpkins fly through the air with a pumpkin launcher, sample the apple donuts, and even mine for gems. This is a full day excursion!

Family Fun Fall Activities in Chicago and Illinois Pumpkin Patch-Kids A

7. Attend a football game

Most Friday evenings are reserved for high school football games across the U.S. and Chicago is no different. Nothing beats donning your school colors, heading to the stadium with family and friends, and cheering the team to a win alongside the rest of your community.

On Saturdays families support the college football teams like U of I in Urbana-Champaign and Northwestern in Evanston. Tailgating is a fun way to spend a fall afternoon or evening.

If your family likes the NFL, there’s always Sunday and the Chicago Bears (or head up to Green Bay to see the Packers play). There are a few home games in the fall and it is one of the best things to do in October before the weather changes.

Looking for other posts about Chicago? You might enjoy our Weekend Getaways Near Chicago and 15 Best Kid Friendly Restaurants in Chicago.

*This post was updated in September 2022.





























  1. You’re welcome! Maybe we’ll run into you there!

  2. Erin, it is a beautiful place to go hiking. You should definitely come explore!

  3. I’m so sorry Jamie. A tropical islands sounds amazing if that makes you feel better. : ) Chicago is great in the fall. Come visit!

  4. Donna where did you move from? We love the pumpkin patch too!

  5. Door County is gorgeous isn’t it? I really love it in the fall. It’s almost too busy in the summer. Good luck finding some apples!

  6. You are welcome Lexie! Most of these ideas can apply to other places, so I’m glad you found some inspiration!

  7. I’m with you Yona! Fudge always sends me running right toward it! I just can’t say no. Do you have a favorite apple recipe? I’m a sucker for apple pie.

  8. Please let me know if you need any other idea! I am also a Chicago Momaboard Mombassador and we do trip itineraries!

  9. Thanks Sinziana. I do love fall. You can’t beat the colors of nature!

  10. Thanks Michelle! It’s beautiful to go hiking in the fall.

  11. Definitely do! Thanks for stopping by Alissa!

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