three kids smiling while holding pumpkins

75 Best Fall and Pumpkin Festivals in Illinois (2023)

It’s the time of year when the air is crisp and the leaves are starting to change, so it’s time to take advantage of the best fall festivities! Here are the best fall festivals, fall activities, and family fun in northern Illinois to check out this fall season!

If you’re looking for great places to go apple picking, check out the 25 Best Apple Orchards in the Chicago area!

1. Chicago Jazz Festival

August 31-September 3 | More Information

The Chicago Jazz Festival returns with performances celebrating all forms of jazz in Millennium Park, at the Chicago Cultural Center and citywide.

2. Nashwood

September 1-September 3 | More Information

Attendees of all ages are encouraged to don their cowboy boots and hats over Labor Day Weekend for three days of FREE live country, bluegrass, blues and Southern rock music, as well as Southern inspired food and drink specials.

3. Naperville Jacyees’ Last Fling

September 1-September 4 | More Information

The Naperville Jaycees’ Last Fling is a family-friendly community festival which takes place over Labor Day Weekend near Downtown Naperville and, for many, is a fun way to say farewell to summer! The Last Fling offers a wide variety of attractions for all ages to enjoy including: music, food and beverage vendors, a Family Fun area, a carnival, unique special events, a business Expo, a parade and more!

4. Taste of Polonia

September 1-September 4 | More Information

For four days, you can enjoy a true cultural experience that includes nonstop live music, dance performances, authentic Polish food and beer, exhibitions, local merchants, a casino, beer garden, a Kids Stage and area filled with great activities, and more!

5. Frankfort Fall Festival

September 2-September 4 | More Information

Each year during Labor Day weekend, over 250,000 visitors gather to the charming Village of Frankfort to enjoy the Frankfort Fall Festival. The festival welcomes over 300 artisans from all over the United States to exhibit their elite products and services.

6. Long Grove Irish Days

September 2 – September 4 | More Information

All eyes will be smiling when the historic shopping district of Long Grove presents Irish Days, a celebration of Irish culture, music, food, and drink.

a wagon on a sunny day with pumpkins

7. Schaumburg Septemberfest

September 2-September 4 | More Information

An outdoor festival featuring entertainment on three stages, a carnival, arts & crafts show, craft beer & wine area, Taste of Schaumburg, Bingo, free pony rides on Saturday, fireworks on Sunday evening, and a Labor Day parade on Monday. Free Admission and Shuttle Bus Service.

8. Wing Out Chicago

September 2-September 3 | More Information

Wing Out Chicago is the perfect place to taste some wings! From Classic Buffalo, Honey Chili, Jerk, Wood Smoked, Sweet and Spicy, Spicy Garlic, Buffalo Blue, Asian Ginger, Southern BBQ, Habanero Hot, and more.

There will be a live music stage and block party too!

9. West Loop Art Fest

September 2-September 3 | More Information

The West Loop Art Fest is the perfect destination for a late summer shopping experience or ambient evening stroll. A diverse range of art mediums will be on display and available for purchase, making this craft show a must-go event this summer. With interactive art, wine tastings, children’s crafts, and live music, this is a fun-filled weekend for the whole family!

10. German American Oktoberfest

September 8-September 10 | More Information

Celebrate German culture in Lincoln Square with beer, pretzels, live music, spaetzle, kids activities, and more!

11. Taste of Chicago

September 8 – September 10 | More Information

Chicago’s favorite food festival returns a bit later this year.

12. Winfield Good Ol’ Days

September 8-September 10 | More Information

Live music, trolley tours, a  parade, a kid’s zone with bouncy houses, face painting, food, and so much more!

aerial view of fall leaves

13. Printers Row Lit Fest

September 9-September 10 | More Information

Celebrate books and literature at the Printers Row Lit fest! In addition to books, there will be readings, demonstrations, and family-friendly activities.

14. Harris Fest: Music and Dance in the Park

September 9 | More Information

Performances spanning ballet, jazz, and contemporary dance, as well as classical music, opera, and interactive workshops will run from 10am to 9pm and be entirely free to the public.

 Daytime programming will include pop-up performances near Millennium Park’s iconic Cloud Gate sculpture and on the Great Lawn, along with masterclasses, workshops, and other activities for visitors of all ages.

In the evening, the Harris will present fully staged performances at the Pritzker Pavilion.

15. Lakeview East Festival of the Arts

The Lakeview East Festival of the Arts flea market showcases more than 150 juried artists featuring paintings, sculpture, photography, furniture, jewelry and more. These original pieces are for sale in a wide range of price ranges. In addition to the art, the Festival has become a center of activity for the weekend with live demonstrations, entertainment stages, family activities and a garden oasis.

September 9-September 10 | More Information

16. Bubblepalooza

September 9 | More Information

a 20th Anniversary Celebration and Kids Music Fest!

17. Art on the Fox

September 9-September 10 | More Information

A fun-filled festival weekend is in store as Art on the Fox makes an exciting return to the charming streets of Downtown Algonquin!

side view of boots and gourds with festival tents in the background

18. World Dumpling Fest

September 9 | More Information

Join the Chicago Cultural Alliance to celebrate and experience diverse cultures throughout Chicago and the world through performance, art, and DUMPLINGS! Dumplings are served from neighborhood-based ethnic restaurants in and around Chicago and aims to highlight the diversity of cultural and community the city has to offer.

19. Scandinavian Day Festival

September 10 | More Information

Enjoy celebrating the cultures of Scandinavia, Denmark, Sweden, Norway, Finland, and Iceland, at this one day festival in South Elgin. There will be food, dance, crafts, and an ABBA salute!

20. Inspired By You Fest

September 10 | More Information

Come enjoy this family-friendly arts festival with community vendors, live performances, vendors, and activities for adults and kids!

21. Morton Pumpkin Festival

September 13 – September 16 | More Information

Interesting Fact: Morton is actually the pumpkin capital of the world! Libby’s Plant in Morton packs 85% of the world’s canned pumpkins, so what is better place to celebrate pumpkin season? If you’re a fan of pumpkin pie, you definitely have to make the pilgrimage to Morton during harvest season. 

The  Morton Pumpkin Festival, hosted by the Morton Chamber of Commerce,  kicks off on September 13th, and the theme this year is Farmin’ Pumpkins. There will be a pumpkin fishing derby, pumpkin idol jr., a pumpkin recipe challenge, a pumpkin bike ride, a pumpkin run, a pumpkin pancake breakfast, a pumpkin parade, and more!

pumpkins with yellow flowers

22. Glendale Heights Oktoberfest

September 14-September 24 | More Information

Experience live entertainment daily including strolling German “Oompah” entertainers in one of the most authentic festival tents. There will be a selection of German Beers and German Food.

To round out the Glendale Heights Oktoberfest experience, there will be vendors with German products, souvenirs, hats, steins, and much much more.

23. Autumn in the Park Festival

September 15-September 16 | More Information

Celebrate Autumn with live music, kids activities, food, and more!

24. Norwood Park Fall Festival

September 15-September 16 | More Information

A music festival with food vendors, a “Littles Zone” with inflatables, a “Kids zone” with laser tag, virtual reality games, and more!

25. Berwyn’s Oktoberfest

September 15-September 16 | More Information

Enjoy live polka music, German cuisine, and of course, beer for the adults!

26. Marshall Autumn Fest

September 15-September 17 | More Information

The City of Marshall in Southern Illinois is essentially known for its Autumn Festival. They have a parade, a golf outing, a pancake breakfast, live music, car, truck and motorcycle show, and plenty of family fun!

27. West Dundee Heritage Fest

September 15-September 17 | More Information

West Dundee Heritage Fest has many fun things to do including a car show, live music, an arts and crafts show, kids activities, fireworks, and a pancake breakfast!

aerial view of pretzels, beer, and other german delicacies

28. Tinley Park Oktoberfest

September 15-September 17 | More Information

Enjoy authentic German food, a carnival, a craft fair, live music, and a ceremonial keg tapping!

29. Fall Fest Des Plaines

September 15-September 17 | More Information

Des Plaines Fall Fest will have bands, a car show, a kid zone with inflatables, face painting, a petting zoo, and more!

30. Elk Grove Village Oktoberfest

September 15-September 16 | More Information

German delicacies, family fun, live polka music and more!

31. Riverwalk Fine Art Fair

September 16-September 17 | More Information

120 juried artists at this Naperville fine art walk.

32. Celebration de los Arboles

September 16-September 17 | More Information

Experience the diverse cultures of Latin America through music, dance, and food in The Morton Arboretum.

33. Deer Park Art Show

September 16-September 17 | More Information

Held on September 16 and 17, this show rocks to live music and is stroller-friendly, kid-friendly, and upbeat! Artist demonstrations, artist booth chats and interactive activities for kids add to the fun. Admission is free and there is plenty of parking.

pumpkins outside reading for picking

34. Happy Times Pumpkin Fest

September 16 – October 29 | More Information

Didier Farms is running a great family-friendly pumpkin festival this year! They’ll have rides, animal land, a corn maze, pony rides, a silly string asylum, and more!

35. Windy Acres Fall Fest

September 16-October 31 | More Information

U-Pick apples, moon bounces, mini golf, kiddie trains, corn mazes, and more!

36. Edgewater Arts Festival

September 16-September 17 | More Information

Head to this artsy neighborhood for an arts festival featuring all mediums. There will be food, music, beautiful handmade goods, an awesome kids area, and more!

37. Ravenswood Art Walk

September 16-September 17 | More Information

Open studios and galleries, pop-up performances and activations, and an outdoor arts market featuring 50+ local makers, live music and dance, food trucks, and a Malt Row beer garden, and more!

38. West Loop Bavarian Block Party

September 16-September 17 | More Information

The Bavarian Block Party will center on an authentic celebration of German culture, complete with popular German foods such as bratwurst and pretzels along with traditional American fare.

The Bavarian Block Party will similarly feature live music, including a mix of German polka bands as well as local rock and pop groups.

39. Family Fall Fest in Rosemont

September 17 | More Information

Enjoy free activities including bounce houses, face painting, a petting zoo, balloon sculptors, pumpkin painting and and musical performances from Jeanie B & The Jelly Beans!

three jack-o-lanterns at night

40. Jack’s Pumpkin Pop Up

September 21-November 5 | More Information

Jack’s Pumpkin Pop Up is one-of-a-kind, outdoor autumn experience complete with pumpkin patches, carnival games, a haunted corn maze, gem mining, fortune tellers, and more.

The festival grounds are packed with fun activities for all ages, but it can get boozy after 7:00pm, so it’s suggested that families with kids attend earlier.

41. Mount Prospect Fall Festival

September 22-September 23 | More Information

Enjoy live music, german cuisine, and family fun!

42. Naperville Irish Fest

September 22-September 23 | More Information

Live Irish music, dance, food, and more!

43. Oaktoberfest

September 22-September 23 | More Information

Celebrate the changing seasons at Oaktoberfest in Downtown Oak Park. Enjoy a premier music line up, delicious fall foods from local restaurants, specialty craft beers, and a Kids Root Beer Garden.

44. Long Grove Apple Fest

September 22-September 24 | More Information

Head to the historic village of Long Grove to celebrate all things apple! There will be an apple pie walk, donuts, caramel dipped to candied apples, apple wine, sangria, plenty of fresh produce and more!

45. Oktoberfest Chicago

September 22-September 24 | More Information

Chicago’s beloved Oktoberfest at St. Alphonsus returns! There aren’t any specific kids activities listed, but they are welcome to enjoy great live music and German food. Sunday is free!

46. Hyde Park Jazz Festival

September 23-September 24 | More Information

Presented on 14 stages across Hyde Park, this remarkable two-day free festival showcases collaboration between academic, cultural and community institutions, and local businesses to present over 30 bands in a variety of settings throughout the Hyde Park neighborhood. Over 20,000 jazz fans and enthusiasts will gather at the event to enjoy more than 18 hours of free, nonstop jazz performances.

square lanterns floating on water at night

47. Water Lantern Fest

September 23 | More Information

The Water Lantern Festival is a family-friendly event filled with great conversation, hope, happiness, fun, and lasting memories!

48. Homewood Fall Festival and Chili Cook-Off

September 23 | More Information

Homewood Fall Fest features live entertainment, a craft faire, a pumpkin patch, children’s crafts, kid-friendly activities, and lots of food. 

Homewood’s Chili Cook-Off will be back again this year! 

49. Eugene Field Park Fall Fest

September 24 | More Information

Bounce houses, animals, carnival games, prizes, and more!

50. Huntley Fall Fest

September 29-October 1 | More Information

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.

51. Lincoln Park Zoo Fall Fest

September 29-October 29 | More Information

Head to this FREE festival at the Lincoln Park Zoo! Attractions include the Fun Slide, a pumpkin-filled Harvest Maze, inflatable attractions, free musical entertainment, story times, professional pumpkin carvers, a pumpkin patch, and fall-themed enrichment for the animals.

apples in basket on fall grass

52. Lincoln Square Ravenswood Apple Fest

September 30-October 1 | More Information

The Lincoln Square apple festival is a favorite annual event in Chicago! Local businesses get creative by incorporating apple into delicious fall foods. There are plenty of family-friendly activities, including live entertainment from the Wiggleworms and other kid-friendly bands. Enjoy some hot apple cider, and don’t miss the Pooch costume contest on Saturday morning at 10:00am!

53. Galena Oktoberfest

September 30 | More Information

You’ve heard of pig races, but where else can you enjoy weiner dog races? Galena Oktoberfest is known for its unique weiner dog races, an plenty of other fun things to do with the family! There will be nonstop live music, food, beer, pumpkin painting, and more!

54. Harvest Fest

September 30 | More Information

The Harvest Festival in Bensonville is one of the best things to do in the autumn season! There are plenty of family-friendly activities, live music, great food, and more! General admission is FREE and there is also free parking available.

The schedule of events includes pumpkin yoga, Subie’s World, face painting, a mechanical pull, a straw pyramid, and more!

55. Oktoberfest in Highland Park

September 30 | More Information

Celebrate German culture with German music, food, and more!

view from bridge of boat on Chicago river

56. Island Party Hut Fall Festival

September 30-October 28 | More Information

This weekly festival is a great way to soak up some fall fun!

At Island Party Hut on the Chicago Riverwalk:

  • Live Music from 1-4pm & 5-8pm
  • Hayrides on the River
  • Fall Cocktails & Beer
  • Apple Cider Donuts
  • Pumpkin Patch
  • Photo Ops
  • Games & More

57. Fox Lake Fall Festival

October 1 | More Information

This FREE event will have music, craft vendors, pumpkin carving, food, refreshments, a pie-eating contest, inflatables, petting zoo, police vehicles, and much more!

58. Pumpkin Fest at Cosley Zoo

October 1-October 31 | More Information

Wheaton’s adorable zoo, Cosley Zoo, is hosting its 39th pumpkin festival for the whole month of October. There will be pumpkins, fall treats, and carnival rides for small kids!

59. Great Highwood Pumpkin Festival

October 6=October 8 | More Information

The Great Highwood Pumpkin Festival is a fall event you don’t want to miss. This family-friendly event will have lots of free entertainment like costume contests, pumpkin decorating and carving, and trick or treating. There will be good food from local vendors, craft vendors, hay rides, a music festival, a superhero 5k, and plenty of opportunities for kids to play games. This annual festival is sure to be a great time for the entire family!

scarecrows in a row in a field

60. St. Charles Scarecrow Festival

October 6-October 8 | More Information

The St. Charles Scarecrow Fest is one of the most unique Illinois festivals! The festival features 85+ handmade scarecrows showcased around town for visitors to view and vote on their favorites. The will be plenty of kids activities around town like Touch-A-Truck, festive photo opportunities, and a professional pumpkin carver!

61. Naperville Oktoberfest

October 6-October 7 | More Information

If you are of German heritage or simply enjoy a good beer garden, you have to check out Naperville’s Oktoberfest! Under a large heated tent, there will be live music, plenty of beer for the adults, authentic German food, and lawn games that will be a good time for the whole family. The kids will love the giant Connect Four and giant Jenga!

62. Family Fall Fest in Elmhurst

October 7 | More Information

The Family Fall Fest in Elmhurst will be a great place for family fun on a Saturday morning! There will be food trucks, an inflatable corn maze, a bounce house, a fall scavenger hunt, trick-or-treating, and plenty of photo opportunities.

63. Boo! at the Zoo

October 7-October 22 | More Information

Head to the zoo in your favorite costume and check out creepy crawlers, and more Halloween-themed surprises. All kids will leave with a sweet treat!

64. Fall Fest at Athletic Field Park

October 7 | More Information

Family fun, pony rides, a petting zoo, train rides, food, music, games and so much more!

65. Lombard Fall Fest

October 7 | More Information

Families can enjoy games, dancing, face painting, a candy hunt and so much more!

brightly colored autumn trees dappled with sunlight

66. Night of 1,0000 Jack-O-Lanterns

October 11-October 22 | More Information

Marvel at hand-carved pumpkins by local artists that line the beautiful pathways of the Chicago Botanic Garden. You’ll find costumed entertainers, live carving demos, lots of varieties of pumpkins, and seasonal treats.  

A walking tour of the botanic garden is one of the best places to spend a Sunday afternoon, and there will be so many perfect pumpkins that you’ll want to make this an annual tradition for the entire family!

67. Glass Pumpkin Patch at Morton Arboretum

October 13-October 15 | More Information

Learn about glass blowing and enjoy the beautiful scenery of Morton Arboretum.

68. Pumpkin Patch at Horner Park

October 14 | More Information

Enjoy Halloween-themed carnival games, inflatables, photo stations, and pumpkin decorating!   Pumpkins are $5, but everything else is free

69. Cantigny Fall Festival

October 14-October 15 | More Information

Head to beautiful Cantigny for their annual fall festival. There will be family-friendly fun announced soon!

70. Pumpkin Patch at Hamlin Park

October 21 | More Information

Enjoy Halloween-themed carnival games, inflatables, photo stations, and pumpkin decorating!

creepy mask with a pink hat

71. Arts in the Dark Parade

October 21 | More Information

The Arts in the Dark Parade is one of the best Halloween parades in the world, and it’s right here in the Windy City! This FREE, family-friendly event celebrates Halloween as the “artists’ holiday” and features spectacle puppets, creative floats, music, movement, and more.

The parade takes place in Downtown Chicago along State Street from Lake Street to Van Buren.

72. Sycamore Pumpkin Festival

October 25-October 29 | More Information

Enjoy some pumpkins, delicious food and drink, live music and plenty of family-friendly activities at this annual festival that has been ranked one of the best festivals in Illinois by Travel Magazine.

73. Pumpkin Palooza

October 28 | More Information

Pumpkin Palooza is full of fun, not frightening festivities for the whole family. 

Special Activities:

  • Build your own FrankenBuddy out of recycled toys
  • Create wearable art
  • Brew your own gooey slime
  • Mix and mash pumpkin guts
  • And More!

74. Centralia Halloween Parade and Festival

October 28 | More Information

Centralia, in Central Illinois, is known for its festivals. Not only do they have an awesome hot air balloon festival, but they. have a fantastic Halloween parade and festival. There will be a chili cook-off, parade, costume contest, live music, and plenty of kid-friendly activities!

75. Haunted Halsted Halloween Parade

October 31 | More Information

Northalsted, Chicago’s beloved gayborhood, goes all out for Halloween. With creative costumes, music, spirited dance, and more, this is the right place to be on Halloween! 

the moon obscured by clouds

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