Free
Free music and a local restaurant showcase take over downtown Arlington Heights.
Going? Keep it.
More on Friday
The Great Highwood Pumpkin FestivalOctober 2–4, 2026; Friday 4–10pm, Saturday noon–10pm, Sunday noon–9pmDowntown Highwood, Highwood, Far SuburbsFree
LE Sserafim – Pureflow TourFri, Oct 2, 2026 · 7:30pmUnited Center, Near West Side, Pilsen, West Town & the West SideOne Day Only
Bill Burr LiveFriday, October 2, 2026, 7:30 PM; Saturday, October 3, 7:00 PM and 10:00 PMThe Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopOne Weekend Only
Lincoln Square Ravenswood Apple Fest 2026Through Oct 4, 2026; Friday 3–7pm, Saturday and Sunday 9am–6pmLincoln Avenue, Lawrence to Sunnyside, Lincoln Square, Andersonville, Uptown & Lincoln Square$5 suggested donation to enterFree
Also in Far Suburbs
More festivals that weekend
Fall Fest at Lincoln Park ZooSeptember 25–November 1, 2026; pumpkin patch open daily, live pumpkin carving weekends 10am–1pmLincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleFreeLimited Run
South Side Science FestivalSaturday, October 3, 2026, 9 a.m.–5 p.m.The University of Chicago, Hyde Park, Bronzeville & the South SideFreeOne Day Only
73rd Annual Chicago PowwowSaturday, October 3, 2026; gates open 10 AM, Grand Entries 11 AM and 3 PMSchiller Woods East, Grove 13, Schiller Woods, Logan Square, Wicker Park & Bucktown$20 adult at the gateLimited Run
More free events →
World Music Festival Chicago: Global Peace PartySunday, October 4, 2026, noon–5pmHumboldt Park Fieldhouse (outdoor), Humboldt Park, Logan Square, Wicker Park & BucktownFreeOne Day Only

Maxwell Street Market – season finaleSunday, October 4, 2026, 10am–3pmMaxwell Street between S. Halsted St. and S. Union Ave., Downtown, the Loop & West LoopFreeOne Day Only
Smart Museum Fall Exhibition OpeningSaturday, October 3, 2026, 2–5pmSmart Museum of Art, Hyde Park, Bronzeville & the South SideFree admissionArt


