Arts & Entertainment
2026 Chicago Festival Guide
Get ready for fun with this guide to neighborhood street fests, art shows, outdoor concerts, cultural celebrations and summer events of all sizes across Chicago and the suburbs. To submit an event for consideration, email [email protected].
Millennium Park Summer Film Series. (Patrick L. Pyszka / City of Chicago)
May 22-Sept. 25: Fourth Fridays Summer Concert Series (Elmhurst) | Map
June 3-Sept. 23: Ravinia Festival (Highland Park) | Map
July 6- Sept. 19: Broadway in Your Backyard | Various locations
Celebración de los Árboles. (Courtesy of Morton Arboretum)
Jump to: October | Recurring Events
Sept. 10-20: Glendale Heights Oktoberfest | Map
Sept. 17: Andersonville Fall Wine Walk | Map
Sept. 17: Lincoln Park Uncorked | Map
Sept. 17-19: Englewood Jazz Festival | Map
Sept. 18-19: Naperville Irish Fest | Map
Sept. 18-20: Old Town Oktoberfest | Map
Sept. 18-20: Riot Fest (Douglass Park) | Map
Sept. 18-20: Norwood Park Fall Fest | Map
Sept. 18-20: Urban Birding Festival | Various locations
Sept. 18-20: Retro on Roscoe (Roscoe Village) | Map
Sept. 19: Ritmo del Mar (Loop) | Map
Sept. 19-20: Lakeview East Festival of the Arts | Map
Sept. 19-20: Riverwalk Fine Art Fair (Naperville) | Map
Sept. 19-20: World Dumpling Fest (Lincoln Park) | Map
Sept. 19-20: Chicago Live! (Navy Pier) | Map
Sept. 19-20: Magnificent Mile Art Festival | Map
Sept. 19-20: Oktoberfest at the Garden (Glencoe) | Map
Sept. 19-20: Greenwich Village Art Fair (Rockford) | Map
Sept. 19-Oct. 30: Sonny Acres Farm Fall Festival (West Chicago) | Map
Sept. 19-Nov. 1: Jack’s Pumpkin Pop-Up (West Town) | Map
Sept. 24-27: St. Helen Carnival (Ukrainian Village) | Map
Sept. 25-26: Oaktoberfest (Oak Park) | Map
Sept. 25-27: Apple Fest (Long Grove) | Map
Sept. 25-27: Oktoberfest Chicago (Lakeview) | Map
Sept. 25-27: Andersonville Arts Weekend | Map
Sept. 25-27: International Festival of Life (Washington Park) | Map
Sept. 25-27: La Grange Oktoberfest | Map
Sept. 25-Oct. 4: World Music Festival Chicago | Various locations
Sept. 26: Hispanic Heritage Fest (Brookfield) | Map
Sept. 26: Tacos and Tequila Festival (Geneva) | Map
Sept. 26: Oktoberfest (Highland Park) | Map
Sept. 26: Rosetober Fest (Rosemont) | Map
Sept. 26-27: Randolph Street Market Festival (West Loop) | Map
Sept. 26-27: Celebración de los Árboles (Lisle) | Map
Sept. 26-27: Hyde Park Jazz Festival | Map
Sept. 26-27: WingOut Chicago (Lakeview) | Map
Sept. 26-27: Clark Street Live (Wrigleyville) | Map
Sept. 27: Meet Me on Milwaukee (Wicker Park) | Map
Apple Fest. (Courtesy of the Lincoln Square Ravenswood Chamber of Commerce)
Jump to: September | Recurring Events
Oct. 1-4: The Great Highwood Pumpkin Fest & Skeletons on Display | Map
Oct. 1-4: Mokena Family Fall Fest | Map
Oct. 2-3: Oktoberfest (Naperville) | Map
Oct. 2-4: West Town Art Walk (West Town) | Various locations
Oct. 2-4: Lincoln Square Ravenswood Apple Fest | Map
Oct. 3: Family Fall Fest (Elmhurst) | Map
Oct. 3: Cider and Ale Festival (Lisle) | Map
Oct. 3: Fall Fest at Lombard Common | Map
Oct. 3-4: Woodstock Art Fair on the Square | Map
Oct. 3-25: Boo! at the Zoo (Brookfield) | Map
Oct. 4: Maxwell Street Market (Near West Side) | 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. 23-24: Zoo Brew: Howls and Growls (Lincoln Park) | 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. 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
