Looking for things to do in Chicago in October 2026? SAVE THIS! 📌 Chicago is packed with fall festivals, Halloween events, pumpkin experiences, food, culture, family activities and date-night ideas. 🎃 MONTH-LONG FALL FUN 🎃 Jack’s Pumpkin Pop-Up | Sept 19–Nov 1 📍 Goose Island • 10,000+ pumpkins, corn maze, games, bars, food trucks & photo ops. 🦁 Lincoln Park Zoo Fall Fest | Sept 25–Nov 1 📍 Lincoln Park • Pumpkins, carving, live music & seasonal activities. 💀 Where Memory Lives | Sept 25–Nov 29 📍 National Museum of Mexican Art • Día de Muertos exhibition celebrating 40 years of tradition. 🍎 Apple Fest | Oct 2–4 📍 Lincoln Square • Apple treats, cider, vendors & live entertainment. 🍺 Cider & Ale Festival | Oct 3 📍 Morton Arboretum • Seasonal drinks surrounded by fall foliage. 🛍️ Maxwell Street Market | Oct 4 Food, vendors, music & Chicago market culture. 🎨 Chicago Art Fair | Oct 7–10 📍 THE MART • Contemporary art & galleries. 🎃 Night of 1,000 Jack-o’-Lanterns | Oct 7–25 📍 Chicago Botanic Garden • Illuminated carved-pumpkin trail. 👗 Chicago Fashion Week | Oct 8–18 📍 Various locations • Runway shows, designers & fashion events. 🍷 Lincoln Park Wine Festival | Oct 9–11 Wine, food & live entertainment—a great Chicago fall date idea. 🎃 Glass Pumpkin Patch | Oct 9–11 📍 Morton Arboretum • Thousands of handcrafted glass pumpkins. 🏠 Pullman House Tour | Oct 10–11 Explore historic Pullman homes rarely open to the public. 🍺 Oktoberfestiversary | Oct 10–11 📍 North Center • Begyle + Dovetail fall celebration. 🏃🏽 Chicago Marathon | Oct 11 Cheer on runners throughout Chicago neighborhoods. 🎬 Chicago International Film Festival | Oct 14–25 Films, premieres & special screenings around Chicago. 👻 Spooky Zoo | Oct 17 📍 Lincoln Park Zoo • Family-friendly Halloween fun. 🏙️ Open House Chicago | Oct 17–18 Explore incredible Chicago buildings and normally restricted spaces. 🍺 Zoo Brews: Howls & Growls | Oct 23–24 📍 Lincoln Park Zoo • 21+ Halloween beer/cider experience. 🎭 Arts in the Dark | Oct 24 • 6–8 PM 📍 Columbus Dr • FREE Halloween parade with puppets, costumes & performers. 🎥 Music Box of Horrors | Oct 24 📍 Music Box Theatre • 24-hour horror movie marathon. 🎃 BOO! at Brookfield Zoo | Oct 24 Family-friendly Halloween activities. 🎤 Chicago Made Music Showcase | Oct 24 📍 Millennium Park • Celebrate Chicago music & local talent. 💀 Memento Mori Halloween Gala | Oct 30 • 21+ 📍 Navy Pier • Halloween night-out experience. 🎃 Slightly Spooky Saturday | Oct 31 📍 Navy Pier • Family Halloween fun. 💀 Carrera de los Muertos | Oct 31 📍 Pilsen • Día de Muertos community race. 👻 Upside Down Halloween Parade | Oct 31 • 12–2 PM 📍 Washington Park • FREE family Halloween celebration. 🎃 Haunted Halsted Halloween Parade | Oct 31 📍 Northalsted • Block party 11–6 • Parade 7–8 • Post-party 8–10. 📌 SAVE this Chicago October 2026 guide and send it to the person always asking, “What are we doing this weekend?” 😂🍂 SEO: Chicago October 2026, things to do in Chicago, Chicago events October 2026, Chicago Halloween events, Chicago fall festivals, Chicago weekend events, Chicago date ideas, free things to do in Chicago, family activities Chicago, Chicago fall bucket list, Chicago travel guide. #Chicago #ChicagoThingsToDo #ChicagoEvents #ChicagoFall #ChicagoHalloween - @siwaslifestyle