Our Favorite Fall Activities in Chicago and Illinois (2026)

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.

*Disclosure: This post may contain affiliate links, which means we may receive a commission if you click a link and purchase something we have recommended. Please check out our disclosure policy for more details. Thank you for your support!

What Are the Best Fall Activities in Chicago and Illinois?

The best fall activities in Chicago and Illinois include visiting the world’s largest corn maze at Richardson’s Adventure Farm, apple picking at local orchards, hiking Starved Rock State Park when the leaves peak, attending fall festivals like the Morton Arboretum’s October events and Naperville Oktoberfest, and picking pumpkins at farms like Goebbert’s in Pingree Grove.

Beyond the city, fall day trips to Galena, the Great River Road, and southern Illinois round out a great season. October is peak month, the weather is crisp, the Lincoln Park Zoo Fall Fest is free every weekend, and pumpkin patches are at their best.

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, sunflower fields, 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. This year’s design celebrates the 250th anniversary of the United States.

Finding all of the checkpoints can take a couple of hours, but if you find a minimum number, 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.

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 includes eight zip lines and three aerial suspension bridges, providing spectacular close-up views of fall foliage in Illinois.

Visit 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 Galena with its charming shops, art galleries, and historic sites.

3. Visit a U-pick apple orchard

One of our favorite fall activities 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! 

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 Run and Walk, 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: October 3-4

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!

The Great Highwood Pumpkin Festival – October 2-4

The city of Highwood celebrates the 15th annual Great Highwood Pumpkin Festival with a pumpkin festival to rival all others.

There are also costume contests, a pumpkin parade, carnival games and rides, and food trucks. Fun times begin on Thursday with Community Pumpkin Carving. Through the weekend, you can find live entertainment, trick-or-treating, and a pie-eating contest. One thing not to miss is the Big Pumpkin Wall Lighting on Saturday 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 25-26

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 25 to November 1

Fall Fest is a free event every weekend through the end of October. Enjoy endless 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.

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. 

Some of our favorite leaf peeping drives 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.

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 attractions 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 through the end of October. Kids can watch pumpkins fly through the air with a pumpkin launcher, sample apple donuts, and even go on 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 the University of Illinois 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.

Best Fall Getaways Near Chicago in Illinois

Not every fall adventure has to stay inside the city. Some of the best fall activities in Illinois are within a two-hour drive of Chicago, making them easy day trips or overnight escapes.

Galena is one of the most scenic fall destinations. The rolling hills around this historic town turn brilliant shades of orange and red, and the charming downtown is full of shops, galleries, and restaurants to explore after a day in the leaves.

Starved Rock State Park in Utica is already in the hiking section above, but it deserves a mention here too. The park is one of the most dramatic fall landscapes in the Midwest, and it fills up fast on weekends; arrive early.

Galena to Galesburg along the Great River Road on the state’s western edge is a gorgeous fall drive. Pull off at the overlooks along the Mississippi, and you’ll feel like you’ve driven into a painting.

Lake Geneva, Wisconsin, is just across the state line and one of our favorite quick fall getaways from Chicago. The lakeshore trail blazes with color in October, and there are plenty of cozy spots for apple cider and a warm meal.

For a longer overnight trip, southern Illinois surprises people every single time. The Garden of the Gods wilderness area and Cave-in-Rock State Park are mentioned in the hiking section, and they feel completely removed from the city, in the best possible way.

What to Do in Chicago in October

October is arguably the best month in Chicago for families. The weather is crisp but still manageable, the crowds thin out, and something is happening every weekend.

The Lincoln Park Zoo Fall Fest runs every weekend through the end of October, and it’s free, a hard combination to beat. The pumpkin patches listed above are in full swing, and the Morton Arboretum’s October events (Night of 1,000 Jack-O-Lanterns, the Fall Color 5K, the Glass Pumpkin Patch) are worth planning around.

The Great Highwood Pumpkin Festival (typically early October) and Naperville Oktoberfest at Naper Settlement are two more October anchors for families. Both are easy day trips from the city.

If your family is into Halloween, October is when Chicago’s haunted houses, spooky tours, and trick-or-treat events kick into gear. The Lincoln Park Zoo’s Haunted History Tours and Spooky Zoo are solid picks for younger kids who want the fun without the frightening.

Don’t overlook the simple stuff. A walk along the lakefront in October, when the trees are turning, is one of those free Chicago experiences that is hard to beat. If you’re looking for more ways to keep the kids entertained around the city, check out our guide to fun things to do in Chicago with teens for ideas that work across ages.

Key Takeaways

• Richardson’s Adventure Farm: world’s largest corn maze, 90 min from Chicago
• Illinois grows more pumpkins than any other state
• Starved Rock State Park: 13+ miles of trails, 18+ canyons
• Lincoln Park Zoo Fall Fest: free every weekend through October
• October is peak month for festivals, pumpkins, and fall color
• Galena and the Great River Road are top Illinois fall day trips
• Check leaf-peeping reports before driving to see fall color

What can I see and do in Chicago during the fall?

Chicago in fall offers corn mazes, pumpkin patches, apple orchards, hiking at nearby state parks, fall festivals at the Morton Arboretum and Lincoln Park Zoo, Oktoberfest celebrations in the suburbs, leaf-peeping drives along Lake Michigan, and NFL and college football games. October is the busiest and most colorful month.

What are some good fall getaways near Chicago?

Great fall getaways near Chicago include Starved Rock State Park in Utica (about 90 miles southwest), Galena in the northwest corner of Illinois for scenic hills and charming shops, Lake Geneva just across the Wisconsin border, the Great River Road along the Mississippi, and southern Illinois for the Garden of the Gods wilderness area and Cave-in-Rock State Park.

What are some fun things to do in Illinois during the fall?

Illinois fall highlights include visiting Richardson’s Adventure Farm (home of the world’s largest corn maze), hiking through the 18-plus canyons of Starved Rock State Park, zip-lining through fall foliage, hot air balloon rides over Galena, apple picking at local orchards, and attending harvest festivals across the state. Illinois also grows more pumpkins than any other state, so pumpkin patches are everywhere.

What are some fun things to do in Chicago in October?

In October, Chicago families can catch the Lincoln Park Zoo Fall Fest (free every weekend through the end of October), the Morton Arboretum’s Night of 1,000 Jack-O-Lanterns and Glass Pumpkin Patch, the Great Highwood Pumpkin Festival, Naperville Oktoberfest at Naper Settlement, and the Oaktoberfest family festival in Oak Park. Pumpkin patches at farms like Goebbert’s and Bengtson’s are also in full swing all month.

What is the best corn maze near Chicago?

Richardson’s Adventure Farm, about 90 minutes north of Chicago near the Wisconsin border, is home to the world’s largest corn maze. The farm also has a petting zoo, zip line, giant slides, and a fudge shop. For a closer option, a ten-acre maze is available in Rantoul near Champaign, along with a pumpkin launching cannon and hay rides.

When do the leaves change color in Illinois?

Fall foliage in Illinois typically peaks in October, with northern areas near Chicago changing first and southern Illinois following a week or two later. Check a leaf-peeping report before heading out to catch peak color. The Illinois River Road, the Great River Road along the Mississippi, and the drive from Chicago to Lake Geneva are popular leaf-peeping routes.

Looking for other posts about Chicago? You might enjoy our Weekend Getaways Near Chicago. We also have our favorite fall events around the US!SaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSaveSave

SaveSaveSaveSavSaveSave