10 Best Things to Do in Chicago and DuPage This Weekend: October 23-25, 2026
CHICAGO— The weekend before Halloween is bringing one of October’s strongest lineups to Chicago and the western suburbs.
Downtown will glow for the Arts in the Dark Halloween Parade, Pilsen is hosting a major Día de los Muertos celebration, the Chicago International Film Festival enters its final weekend, and the Chicago Bulls are back at the United Center.
Head into DuPage County and families can race pumpkins through Downtown Naperville, trick-or-treat through Cantigny and historic Naper Settlement, or take a free Halloween trolley ride between Downtown Naperville businesses.
Here are 10 of the best things to do in Chicago and DuPage County from Friday, October 23 through Sunday, October 25, 2026.
1. Arts in the Dark Halloween Parade
When: Saturday, Oct. 24, 6-8 p.m.
Where: Columbus Drive, beginning at Balbo Drive in Downtown Chicago
Admission: Free
Chicago’s massive nighttime Halloween parade returns Saturday with illuminated floats, giant puppets, elaborate costumes, dancers, musicians and performers from cultural and youth arts organizations across the city.
This year marks the 12th annual Arts in the Dark, with the parade returning to Columbus Drive. Organizers recommend arriving early, especially if you want a good viewing spot.
If you are coming with kids, consider watching closer to Balbo and combining the evening with an afternoon in Grant Park, Millennium Park or Maggie Daley Park.
2. Día de los Muertos Xicágo
When: Saturday, Oct. 24, 3-8 p.m.
Where: Harrison Park, 1824 S. Wood St., Pilsen
Admission: Free
One of Pilsen’s biggest cultural events of the season returns outside the National Museum of Mexican Art.
Día de los Muertos Xicágo transforms Harrison Park and the museum surroundings into a space honoring loved ones who have died. Visitors can see community-created ofrendas, participate in art activities and watch live music and performances throughout the afternoon and evening.
The museum’s 40th annual Día de Muertos exhibition, Where Memory Lives, is also currently on view, making Saturday a particularly good time to spend several hours exploring Pilsen.
3. 62nd Chicago International Film Festival
When: Friday through Sunday, Oct. 23-25
Where: Multiple Chicago venues
Admission: Ticket prices vary by screening
This is the final weekend of North America’s longest-running competitive film festival.
The 62nd Chicago International Film Festival has been screening more than 150 films from around the world since October 14, with the final round of features, documentaries, shorts and filmmaker appearances scheduled through Sunday.
Instead of treating it like a normal trip to the movies, look for an international feature, documentary or filmmaker event you would be unlikely to catch during a regular theater weekend.
4. Zoo Brews: Howls and Growls
When: Friday and Saturday, Oct. 23-24, 6:30-10 p.m.
Where: Lincoln Park Zoo, 2001 N. Clark St.
Admission: Ticketed, 21+
Lincoln Park Zoo turns into an adults-only Halloween party for two nights.
Zoo Brews includes craft beer and cider sampling stations around the grounds, a live DJ, roaming entertainment, pumpkin carving, a costume contest and unlimited rides on select attractions.
If beer sampling is not your thing, the zoo’s regular Fall Fest also continues through the weekend, with free zoo admission and optional seasonal attractions.
5. Slightly Spooky October at Navy Pier
When: Saturday, Oct. 24, beginning at 1 p.m.
Where: Navy Pier, 600 E. Grand Ave.
Admission: Free
Navy Pier is one of the weekend’s easiest options if October weather turns unpredictable.
Saturday’s Halloween programming includes family activities, hands-on experiences and seasonal entertainment during the afternoon, followed by free movie programming later in the evening.
Because so much of the activity is indoors, families can keep this one in mind as a backup plan even if rain changes other weekend plans.
6. Washington Wizards vs. Chicago Bulls
When: Saturday, Oct. 24 at 7 p.m.
Where: United Center, 1901 W. Madison St.
Admission: Ticketed
The Chicago Bulls are home Saturday night, hosting the visiting Washington Wizards at the United Center.
For our event guides, sports matchups are listed Visitor Team vs. Home Team, so this one is Washington Wizards vs. Chicago Bulls.
Tipoff is scheduled for 7 p.m., making this a strong Saturday-night option for anyone who wants a break from the weekend’s Halloween-heavy calendar.
Arrive early and you can also turn it into a Near West Side night out. The United Center sits minutes from West Loop and Fulton Market, giving fans plenty of options for dinner before the game.
For Chicago fans, though, the main attraction is straightforward: the Bulls are defending home court at the United Center.
7. Family Night Trick-or-Treating at Cantigny
When: Friday, Oct. 23, 5:30-7:30 p.m.
Where: Cantigny, 1S151 Winfield Road, Wheaton
Admission: Park admission charged by vehicle
Friday night offers an easy family Halloween outing at Cantigny.
Children can follow a trick-or-treat route through the park with multiple candy stations and seasonal activities along the way.
The setting makes this especially appealing if you want an outdoor Halloween experience without committing to an entire evening of door-to-door trick-or-treating.
8. 10th Annual Naperville Pumpkin Race
When: Saturday, Oct. 24, noon-3 p.m.
Where: Rotary Hill Park, Downtown Naperville
Admission: Free to attend; pumpkin race kits sold separately
This may be Naperville’s most unusual fall tradition.
The Naperville Pumpkin Race celebrates its 10th anniversary Saturday, with participants turning pumpkins into four-wheeled racers and sending them head-to-head down the course at Rotary Hill.
The afternoon also includes costume and pumpkin-decorating contests, with proceeds from race kits supporting Turning Pointe Autism Foundation.
Rotary Hill sits beside the Naperville Riverwalk and Millennium Carillon, so leave time for a walk before or after the racing.
9. Family Spooktacular at Naper Settlement
When: Saturday, Oct. 24, 10 a.m.-2 p.m. and Sunday, Oct. 25, noon-4 p.m.
Where: Naper Settlement, 523 S. Webster St., Naperville
Admission: Ticketed
Naper Settlement’s historic buildings become trick-or-treat stops during its Family Spooktacular weekend.
Families can collect candy across the museum’s 13-acre campus while taking part in kid-friendly Halloween activities and live entertainment.
It is one of the stronger options if you want an event that can occupy the family for several hours instead of a quick trick-or-treat stop.
10. Downtown Naperville Halloween Hop
When: Sunday, Oct. 25, 10 a.m.-noon
Where: Downtown Naperville
Admission: Free
Finish the weekend with an old-fashioned downtown trick-or-treat route.
The Halloween Hop sends families between participating businesses throughout Downtown Naperville, with additional activities and free Trick-or-Treat Trolley rides helping families move around the area.
Because Downtown Naperville connects directly with the Riverwalk, it is easy to continue into lunch and an afternoon walk after the Halloween activities finish.
This Is the Weekend Halloween Takes Over Chicagoland
The variety is especially good from October 23-25.
Downtown Chicago has a massive free nighttime parade. Pilsen offers a community Día de los Muertos celebration. Film lovers get the final weekend of the Chicago International Film Festival, while sports fans can watch the Washington Wizards visit the Chicago Bulls at the United Center.
In DuPage, families can spend almost the entire weekend around Wheaton and Naperville, moving from Cantigny’s Friday trick-or-treating to pumpkin racing Saturday and Downtown Naperville’s Halloween Hop on Sunday.
Event schedules, ticket availability and weather plans can change, so check the official event page before leaving, particularly for ticketed programs and outdoor activities.
Exploring Chicago or the Western Suburbs This Weekend?
Community events are an easy way to experience somewhere beyond its listing photos.
Walk West Loop, Pilsen, Wheaton or Downtown Naperville during a busy weekend and you begin noticing how residents actually use the parks, businesses, transit, public spaces and neighborhood gathering places around them.
The Cory Tanzer Group at Option Premier helps buyers and relocation clients compare communities across Chicago, the North Shore and the Western Suburbs, including the housing and everyday lifestyle surrounding each property.
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