Arts & Entertainment

2026 Chicago Festival Guide

Get ready for fun with this guide to neighborhood street fests, art shows, outdoor concerts, cultural celebrations and events of all sizes across Chicago and the suburbs. To submit an event for consideration, email [email protected].

---

Apple Fest. (Courtesy of the Lincoln Square Ravenswood Chamber of Commerce)

Sept. 19-Oct. 30: Sonny Acres Farm Fall Festival (West Chicago) | Map

Sept. 19-Nov. 1: Jack’s Pumpkin Pop-Up (West Town) | Map

Oct. 3-25: Boo! at the Zoo (Brookfield) | Map

Oct. 7-25: Night of 1,000 Jack-o’-Lanterns (Glencoe) | Map

Oct. 8: Hinsdale Wine Walk | Map

Oct. 9-11: Lincoln Park Wine Fest | Map

Oct. 9-11: St. Charles Scarecrow Fest | Map

Oct. 9-11: Glass Pumpkin Patch (Lisle) | Map

Oct. 10: Stews & Brews (Highland Park) | Map

Oct. 10: Food Truck Festival (West Pullman) | Map

Oct. 10-11: Oktoberfestiversary (North Center) | Map

Oct. 17: Nightmare on Chicago Street (Elgin) | Map

Oct. 17: Spooky Zoo (Lincoln Park) | Map

Oct. 17: Loop Arts Fest | Map

Oct. 23-24: Zoo Brew: Howls and Growls (Lincoln Park) | Map

Oct. 23-24: Howlin’ at the Moon (Naperville) | Map

Oct. 24: Harvest on Harrison (Oak Park) | Map

Oct. 24: Arts in the Dark Halloween Parade (Loop) | Map

Oct. 24: BatFest (Batavia) | Map

Oct. 24-25: Family Spooktacular (Naperville) | Map

Oct. 25: Lincoln Scared (Lincoln Square) | Map

Oct. 25: Boo Bash (Tinley Park) | Map

Oct. 25: Meet Me on Milwaukee (Wicker Park) | Map

Oct. 31: Haunted Halsted Halloween Parade (Northalsted) | Map

Oct. 31: Wheaton Illinois Haunted Flea Market | Map

---