Chicago is buzzing with celebrations this Halloween weekend – and beyond! From spooky parades and pumpkin pop-ups to family-friendly museum events, there’s something for everyone to enjoy. Whether you’re dressing up for the Haunted Halsted Parade, exploring Jack’s Pumpkin Pop-Up, or taking the kids to the Peggy Notebaert Nature Museum for its Día de los Muertos celebration, the city is alive with fall fun and cultural traditions. Here are a few can’t-miss events happening around Chicago this weekend.
💀 Día de los Muertos Celebration at the Peggy Notebaert Nature Museum
📍 Location: 2430 N Cannon Dr, Chicago, IL 60614
📅 Date: Sunday, November 2, 2025
⏰ Event Hours: 11:00 AM – 11:45 AM (additional session at 2:00 PM)
💰 Admission: Free with museum entry
More Info
This family-friendly celebration honors Día de los Muertos with bilingual storytelling, hands-on crafts, and nature-focused activities. Families can visit the museum’s colorful ofrenda, learn about the cultural traditions of remembrance, and join a guided prairie walk exploring the connection between monarch butterfly migration and the holiday’s themes. It’s a warm and educational experience blending art, culture, and nature for all ages.
🎃 Halloween Open House at Lilliput Books
📍 Location: 2150 N Halsted St, Chicago, IL 60614
📅 Date: Friday, October 31, 2025
⏰ Event Hours: All day (store hours)
💰 Admission: Free
More Info
Come celebrate Halloween in-store with trick-or-treat candy, a dog costume contest (with prizes for the best dressed pup), a “book/puzzle blind date” promotion, and spooky bookmark coloring. Kids, pets and families are all welcome for a fun, casual holiday event.
🎃 Jack’s Pumpkin Pop-Up 2025
📍 Location: 1265 W Le Moyne St, Chicago, IL 60642
📅 Dates: Now through Sunday, November 2, 2025
⏰ Event Hours: Vary by day (typically 2:00 PM – 10:00 PM on weekends)
💰 Admission: Tickets start around $25 (children under 3 free)
More Info
Jack’s Pumpkin Pop-Up is Chicago’s ultimate outdoor fall playground – part pumpkin patch, part carnival, part photo paradise. Spanning more than two acres, it features a massive corn maze, pumpkin picking, seasonal treats, and endless fall-themed photo ops. Adults can enjoy cocktails in the beer garden, while kids love exploring the hay bales, gem-mining stations, and games. It’s a perfect blend of cozy autumn vibes and city fun, just off Goose Island.
🎃 Haunted Halsted Halloween Parade 2025
📍 Location: Northalsted – Halsted Street at Belmont Avenue, Chicago, IL
📅 Date: Friday, October 31, 2025
⏰ Event Hours: 6:30 PM – 10:00 PM (Costume registration at 6:30 PM, parade begins at 7:30 PM)
💰 Admission: Free
More Info
The Haunted Halsted Halloween Parade is Chicago’s most iconic Halloween celebration, taking over Northalsted with dazzling costumes, music, and a lively community vibe. The event includes a massive costume contest with $4,000 in prizes across categories like Best Group, Scariest, Most Creative, and Youth (under 13). The parade marches up Halsted Street from Belmont to Brompton, with thousands of spectators lining the route. It’s a festive, inclusive, and high-energy night that brings out Chicago’s creativity in full force.
🍂 No matter how you choose to celebrate, Chicago is the perfect backdrop for fall fun. From festive streets to cozy neighborhood gatherings, the city comes alive with creativity, culture, and community this time of year. So bundle up, grab your favorite pumpkin treat, and make the most of the season, there’s always something magical happening right here in our city.
Curious on what fall events you missed last weekend? Check it out here!