Arts & Entertainment
2025 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].
Rockin' in the Park Concert Series. (Courtesy of Village of Rosemont)
May 31-Sept. 21: Lakeside Pavilion Free Outdoor Summer Series (Glen Ellyn) | Map
June 5-Sept. 11: Record Row Concert Series (Near South Side) | Map
Maxwell Street Market. (Walter S. Mitchell III / City of Chicago)
Jump to: October | Recurring Events
Sept. 3-7: Sandwich Fair | Map
Sept. 5-7: German American Oktoberfest (Lincoln Square) | Map
Sept. 5-7: Retro on Roscoe (Roscoe Village) | Map
Sept. 5-7: Taste of Chicago (Loop) | Map
Sept. 5-7: Festival of the Vine (Geneva) | Map
Sept. 5-7 Throwback Music Fest (Norwood Park) | Map
Sept. 5-7: Mandala Makers Fest (Lakeview) | Map
Sept. 5-7: Winfield Good Old Days | Map
Sept. 5-7: Edgewater Music Fest | Map
Sept. 6: Vintage Car Show (Highland Park) | Map
Sept. 6: Adults Night Out: The Rewilding (Lincoln Park) | Map
Sept. 6: Little Lawndale in the Park (North Lawndale) | Map
Sept. 6-7: Art on the Fox (Algonquin) | Map
Sept. 6-7: Printers Row Lit Fest | Map
Sept. 6-7: Renegade Craft Fair (Wicker Park) | Map
Sept. 6-7: Evanston Folk Festival | Map
Sept. 7: Scandinavian Day (South Elgin) | Map
Sept. 7: Sundays on State (Loop) | Map
Sept. 10-14: Sound & Gravity Festival (Avondale) | Map
Sept. 12-13: Norwood Park Fall Fest | Map
Sept. 12-14: Urban Birding Festival | Various locations
Sept. 13: Food Truck Festival (West Pullman) | Map
Sept 13-14: Highland Park Vintage Shindig | Map
Sept. 13-14: Highwood Arts, Crafts and Drafts | Map
Sept. 13-14: Lakeview East Festival of the Arts | Map
Sept. 13-14: Ravenswood Artwalk | Map
Sept. 14: Maxwell Street Market (Near West Side) | Map
Sept. 14: Family Fall Fest (Rosemont) | Map
Sept. 18-20: Englewood Jazz Festival | Map
Sept. 19: ‘80s vs ‘90s Night at the Zoo (Lincoln Park) | Map
Sept. 19-20: Naperville Irish Fest | Map
Sept. 19-21: Riot Fest (Douglass Park) | Map
Sept. 20: Tacos and Tequila Festival (Geneva) | Map
Sept. 20: Oktoberfest (Highland Park) | Map
Sept. 20-21: Riverwalk Fine Art Fair (Naperville) | Map
Sept. 20-21: Woodstock Art Fair on the Square | Map
Sept. 20-21: Halfway to St. Patrick’s Corned Beef Festival (West Loop) | Map
Sept. 20-21: Chicago Live! (Navy Pier) | Map
Sept. 26-28: Apple Fest (Long Grove) | Map
Sept. 26-28: Oktoberfest Chicago (Lakeview) | Map
Sept. 26-28: Hyde Park Jazz Festival | Map
Sept. 26-Oct. 5: World Music Festival Chicago | Various locations
Sept. 27: HOPtober Fest (Wheaton) | Map
Sept. 27: Hispanic Heritage Fest (Brookfield) | Map
Sept. 27-28: Randolph Street Market Festival | Map
Sept. 27-28: Celebración de los Árboles (Lisle) | Map
Sept. 28: Meet Me on Milwaukee (Wicker Park) | Map
Sept. 28: Oktoberfest (Brookfield) | Map
Arts in the Dark Halloween Parade, 2024. (Raf Winterpacht Photography)
Jump to: September | Recurring Events
Oct. 2-5: Halloween Hollow (Mokena) | Map
Oct. 3-4: Oktoberfest (Naperville) | Map
Oct. 3-5: Lincoln Park Wine Fest | Map
Oct. 3-5: The Great Highwood Pumpkin Fest & Skeletons on Display | Map
Oct. 3-5: West Town Art Walk (West Town) | Various locations
Oct. 3-5: Andersonville Arts Weekend | Map
Oct. 4: Family Fall Fest (Elmhurst) | Map
Oct. 4: Cider and Ale Festival (Lisle) | Map
Oct. 4: Fall Fest at Lombard Common | Map
Oct. 4: Villa Park Brewfest | Map
Oct. 4-5: Lincoln Square Ravenswood Apple Fest | Map
Oct. 4-31: Boo! at the Zoo (Brookfield) | Map
Oct. 5: Sundays on State (Loop) | Map
Oct. 5: Andersonville Fall Wine Walk | Map
Oct. 8-26: Night of 1,000 Jack-o-‘Lanterns (Glencoe) | Map
Oct. 9: Hinsdale Wine Walk | Map
Oct. 10-12: St. Charles Scarecrow Fest | Map
Oct. 10-12: Glass Pumpkin Patch (Lisle) | Map
Oct. 11: Slow & Low Chicago Lowrider Festival (Navy Pier) | Map
Oct. 11: Zoo Fiesta (Lincoln Park) | Map
Oct. 11: Stews & Brews (Highland Park) | Map
Oct. 11-12: Harvest Pow Wow (Wheaton) | Map
Oct. 11-12: Oktoberfestiversary (North Center) | Map
Oct. 12: Maxwell Street Market (Near West Side) | Map
Oct. 17-18: All Hallows Eve (Naperville) | Map
Oct. 18: Spooky Zoo (Lincoln Park) | Map
Oct. 18: Arts in the Dark Halloween Parade (Loop) | Map
Oct. 24: Adults Night Out: Howl-o-ween (Lincoln Park) | Map
Oct. 25: Zoo After Dark: Boos & Brews (Brookfield) | Map
Oct. 25: Nightmare on Chicago Street (Elgin) | Map
Oct. 25: BatFest (Batavia) | Map
Oct. 25: Wheaton Illinois Haunted Flea Market | Map
Oct. 26: Lincoln Scared (Lincoln Square) | Map
Oct. 26: Boo Bash (Tinley Park) | Map
Oct. 26: Meet Me on Milwaukee (Wicker Park) | Map
