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Our Favorite Fall Activities in Chicago and Illinois (2023)

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 apple cider and apple doughnuts in no time. Don’t miss these fun Chicago fall activities.

Our Favorite Fall Activities in Chicago - 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. 

Walking through corn maze fall activities in Chicago Illinois

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. 

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! 

Many local farms offer smaller mazes, family activities, and harvest festivals. This is one of our favorite fall activities in Chicago. Head to one near you, we promise the whole family will enjoy it!

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.

Shawnee National Forest waterfall

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. 

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.

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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 apple picking at one of the local orchards. Finding the best apples is an annual event in our house. One of our favorite places to go is Apple Holler in Wisconsin. 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 near Chicago and the suburbs. Don’t miss our mouthwatering apple recipes. There’s more to make with those apples than apple pies! 

Apple picking

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 fall activities in Chicago begin in September and continue through the end of October. Some of the favorites include:

The Morton Arboretum

Enjoy fall in Chicago 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 Color Wine Tasting, the Glass Pumpkin Patch, Cider and Ale Festival, Family 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, authentic German food, 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

The Great Highwood Pumpkin Festival – October 6-8

The city of Highwood celebrates the 10th annual Great Highwood Pumpkin Festival with a pumpkin festival to rival all others. This year they will once again 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 games and rides, and food trucks. Fun times for everyone begin on Thursday with Community Appreciate Night. Through the weekend you can find live entertainment, trick or treating, and a pie eating contest. The event culminates with the big pumpkin lighting on Sunday night.

Chicago Botanic Garden Fall Fun

The Chicago Botanic Garden in Glencoe has fabulous fall events. This year they have Night of 1,000 Jack-O-Lanterns with live bands, costumed entertainers, and seasonal food and drink.

Kids-Friendly Oktoberfest at Oaktoberfest – September 23

Who says kids can’t enjoy this annual festival? This family-friendly event in downtown Oak Park features traditional German beer and wine for adults, but kids have a beer garden of their own. 

The Kids’ Root Beer Garden happens on Saturday and families can enjoy face painting, balloon making, food vendors from local restaurants, and even zucchini races! There’s free admission, live music, and delicious fall foods. This family-friendly celebration is sure to entertain all ages.

Lincoln Park Zoo Fall Fest – September 29 to October 29

Fall Fest is a free event every weekend through the end of October. There’s an endless amount of family-friendly activities from amusement rides to an obstacle course, ferris wheel, and fun house. Other seasonal events for family-friendly fun include Haunted History Tours and Spooky Zoo.

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There are many other festivals not to be missed around the state. Head to 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. 

Fall on the shores of Lake Michigan

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 fall colors you will find! And if you’re looking to go further afield, don’t miss these fabulous Midwest fall drives

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 Pingree Grove, IL – Located northwest of Chicago, this family farm has a fall festival, u pick pumpkin farm, petting farm, and a pumpkin eating dinosaur. There’s even a haunted house! There are so many kid-friendly activities, plan on spending the day here.

Fall Activities in Chicago pumpkin patch

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 pumpkin picking, the farm has pumpkin fest from September 2nd through the end of October. Kids can watch pumpkins fly through the air with a pumpkin launcher, sample the apple donuts, and even train rides. This is a full day excursion!

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.

Wrap Up: Our Favorite Fall Activities in Chicago

There are so many choices if you are looking for fall fun in Chicago. It’s our favorite time of year in the Windy City and we have a feeling you will agree!

Looking for other posts about Chicago? You might enjoy our Weekend Getaways Near Chicago and 15 Best Kid Friendly Restaurants in Chicago. We also have our favorite fall events around the US!