By Sue Zeiler

As the air turns crisp and the leaves begin to change, Chicago and its surrounding suburbs come alive with a harvest of exciting, family-friendly fall activities and festivals. From pumpkin patches and corn mazes to lively Oktoberfests and traditional apple fests, there is no shortage of seasonal fun for everyone to enjoy. Our comprehensive guide has gathered the top family-friendly events happening in and around Chicago this season to celebrate the best of Fall. Get ready to plan your perfect autumn outing and make lasting memories with our ultimate guide to fall fun! See our top picks for Chicago's best fall fun activities below, and visit to see a full listing on our Fall Fun calendar page!

September 5 – September 7
Chicago German-American Oktoberfest
Lincoln Square, 4521 Lincoln Ave, Chicago
Try authentic German food and traditional drinks. Dance to the music of German bands and spend the evening with friends and enjoy a fabulous festival. Traditional singing and dancing groups from Chicago will perform on Saturday after the parade and on Sunday at 2pm. Add to your entertainment with a visit to the amusement section of the fest and enjoy the many carnival games. Friday 5-10, Saturday and Sunday Noon - 10. FREE. All ages.
Learn more

---

September 12 – September 14
Des Plaines Fall Fest
Lake Park, 2200 Lee Street, Des Plaines
The free festival offers live music and entertainment, with a carnival, a Kid Zone, car show, food and vendors. All ages. Friday 6-11pm, Saturday noon-11pm, Sunday noon-7pm. FREE.
Learn more

---

September 26-27
Fall Festival
Downtown Oak Park, Marion Street and North Boulevard, Oak Park
Celebrate the changing seasons at Oaktoberfest in Downtown Oak Park. Enjoy an exciting live music line up, delicious foods from local restaurants, specialty craft beers, and a Kids Root Beer Garden. Friday 4pm to 10pm | Saturday 12pm to 10pm. FREE. All ages.
Learn more

---

September 14
Fall Festival
Parkway Bank Park, 5501 Park Place, Rosemont
This family-friendly event will feature a variety of free activities including bounce houses, face painting, a petting zoo, pumpkin painting, balloon sculptors and more! Families can also rock out to music about the seasons, food, love and more with family entertainment group, Jeanie B! and The Jelly Beans. Offering music for children of all ages, Time Out Chicago calls Jeanie B! “One of the best things to happen to kids in Chicago in the past decade.” 1-5pm. FREE. All ages.
Learn more

---

September 15 – October 30
Fall Fun at Dollinger Farm
Dollinger Family Farm, 7502 E. Hansel Rd, Channahon
Come and find your perfect pumpkin for carving, decorating, or making a pie. There is also a wide variety of gourds, squash, corn shocks, straw bales, mums, and mini pumpkins. Fall fun on the farm includes a 4-acre corn maze, farm animals, a bee barn, corn bin, Tipi, hay rides, train rides and more. Fees for some activities like corn maze, face painting and train. Admission is free with tickets required for some activities like the Corn Maze, Face Painting and Train Ride. 10:00am - 6:00pm. Free admission, fees for some activities. All ages.
Learn more

---

September 18 – October 26
Happy Times Pumpkin Fest
Didier Farms, 16678 W. Aptakisic Rd., Lincolnshire
Pumpkin Fest will feature family activities and attractions for all ages including amusement rides, shows, fall merchandise, pumpkin sales, and of course everyones favorite fall treats such as apple cider donuts, fudge, and much more. Daily 10am - 6pm, closed Tuesdays. Free entry, fees for activities. All ages.
Learn more

---

September 20 – November 2
Pumpkin Fest
Siegel's Cottonwood Farm, 17250 S. Weber Road, Crest Hill
Siegel’s Cottonwood Farm Pumpkin Fest takes place on a real operating family farm year-round, with a real Pumpkin Field where families can pick a pumpkin right off the vine. Visit have farm animals common to operating farms, with activities and attractions spaced out throughout our vast property. It's a country farm in the city that encourages families of all ages into the fresh air for affordable fun. 10am - 6pm. See web site for cost. All ages.
Learn more

---

September 26 – October 26
Fall Fest
Lincoln Park Zoo, 2200 N. Cannon Dr., Chicago
Chicago’s free and family-friendly fall celebration returns to Lincoln Park Zoo with a full slate of harvest-time fun! From picking the perfect pumpkin and toasting s’mores over a fire pit to rides and entertainers, this festival offers something new and different each weekend in late September and throughout October. Enjoy free musical entertainment, professional pumpkin carvers, a pumpkin patch, and fall-themed enrichment for zoo animals. Closes at 4:30pm on October 11 and 24. 10am - 5pm. FREE with some ticketed activites. All ages.
Learn more

---

September 26 – September 28
Long Grove Apple Fest
Downtown Long Grove, 308 Old McHenry Rd, Long Grove
Long Grove’s Apple Fest is known for the apple pies, donuts, caramel dipped to candied apples, apple wine, sangria, and more, plus a stage full of great rhythm and sounds showcasing all your favorite styles of music. Indulge yourself (and your taste buds) with three fun-filled days that the entire family (including your fur-baby) can enjoy. Friday noon - 11pm, Saturday 11am - 11pm, Sunday noon - 6pm. See web site for pricing. All ages.
Learn more

---

September 26 – September 28
Huntley Fall Fest
By Diecke Park, 12015 Mill St., Huntley
Fall Fest is a three-day community celebration brought to you by the Huntley Fall Fest Committee, generous business sponsors, civic organizations, and hundreds of volunteers. The Huntley Fall Fest features THREE DAYS of entertainment, a beer garden, food vendors, a full carnival midway, plenty of fall activities, and a spectacular fireworks display on Saturday night! It’s the can’t miss event of the year! Fees for carnival. Friday 5-11pm, Saturday 10-11pm, Sunday 11am-7pm. FREE. All ages.
Learn more

---

September 29
Brookfield Zoo Oktoberfest
Brookfield Zoo, First Avenue and 31st Street, Brookfield
Prost! to Oktoberfest at Brookfield Zoo Chicago. This German-style event, which takes place on the Zoo’s Carousel Plaza, is free with general admission. Enjoy family-friendly fun with music, dancing, games and more! Enjoy Live polka music, festive themed giveaways and seasonal menu items including bratwurst, specialty beers, pretzels with cheese, and much more available for purchase. 10am - 5pm. Regular admission. All ages.
Learn more

---

October 2 – October 5
15th Annual Great Highwood Pumpkin Fest
Downtown Highwood, Washington and Sheridan, Highwood
This family friendly, fan favorite event will offer, three days of live music from three stages, children’s and pet costume contest, pumpkin pie eating contests, trick or treating, seasonal interactive installations, a variety of food and artisan vendors, full bars, a carnival, and more! And, to kick it all off, the iconic Pumpkin Fest skeletons will be going up throughout Highwood beginning the weekend of September 27 to get the community in the Fall spirit. Thursday 4-9. Friday 4-10, Saturday 12-10, Sunday 12-9. Free admission, fees for carnival. All ages.
Learn more

---

October 3 – October 5
38th Annual Apple Fest
Lincoln Avenue between Lawrence and Sunnyside, Lincoln and Lawrence, Chicago
Usher in the Fall with the Lincoln Square Ravenswood Chamber of Commerce's 38th Annual Apple Fest! The festivities will take place on Friday, October 3rd from 3-7pm, and Saturday, October 4th and Sunday, October 5th from 9am - 6pm. Apple Fest is a long standing tradition in Lincoln Square, bringing community together to celebrate the beginning of autumn. Friday 3-7pm, Saturday 9am - 6pm & Sunday 9am - 6pm. FREE. All Ages.
Learn more

---

October 3 – October 4
Oktoberfest at Naper Settlement
Naper Settlement, 523 S. Webster St., Naperville
Traditional German cuisine and beer will be overflowing in a giant heated tent, with lively Oompah music on Friday and a mix of Oompah music, modern polka, pop, and country on Saturday. Enjoy one of the largest Oktoberfest beer varieties in the area and German food from local restaurants and food trucks! Guests can test their strength in a stein-holding contest on Saturday from 5-5:30 p.m. The Oscar Mayer Wienermobile will be at Oktoberfest on Friday, October 3 from 5-10 p.m. Come snap a photo next to the Wienermobile! Friday 5 -10pm, Saturday 3 - 10pm. $25/Adult, $15/Child. All ages.
Learn more

---

October 10 – October 12
St. Charles Scarecrow Weekend
Downtown St. Charles, Rte. 64 at Fox River, St. Charles
The 40th annual Scarecrow Weekend will be held October 10th-12th in downtown St. Charles, Illinois. 110+ handmade scarecrows will be showcased around town for visitors to view and vote on their favorites. There will be a Family Zone with live entertainment and family fun as well as an Activity Zone with festive photo ops, Scarecrow-to-Go and family activities. Attendees can also enjoy live entertainment on the 1st Street Plaza throughout the weekend, too! Friday 12-6pm, Saturday 10am - 6pm, Sunday 10am - 5pm. FREE. All ages.
Learn more

---

October 11 – October 12
Harvest Pow Wow
DuPage County Fairgrounds, 2015 Manchester Road, Wheaton
Join us for the Annual Midwest SOARRING Foundation Harvest Pow Wow. Bring your friends and family. All are welcome at our family fun event. Our traditional Powwow is a time to celebrate life, renew friendships, and share our Native American culture through dance, drumming, art, and story telling. See web site for schedule. Adults $17, Seniors 62+ $12, Kids 3-12 $7, under 3 free. All ages.
Learn more

---