Things to Do in Chicago and DuPage This Weekend: October 9–11, 2026

CHICAGO: This may be one of the busiest fall weekends of October!

The Bank of America Chicago Marathon takes over the city Sunday, Chicago celebrates its newly proclaimed Best Big City Day on Saturday, and the weekend also brings wine, fashion, architecture and independent art. In DuPage County, the fall calendar is just as strong with 8,000+ glass pumpkins at The Morton Arboretum, horses and family activities at Danada, Halloween fun in Wheaton and OAKtoberfest in Glen Ellyn.

Here are 10 events happening Friday, October 9 through Sunday, October 11, 2026.

1. Bank of America Chicago Marathon

When: Sunday, October 11; professional race starts begin at 7:20 a.m., with runner waves starting from 7:35 a.m.
Where: Starts and finishes in Grant Park; course travels through 29 Chicago neighborhoods
Admission: Free to watch along the course; some premium viewing areas are ticketed

More than just a race, Marathon Sunday turns huge sections of Chicago into one continuous cheering section. The official course takes runners through 29 neighborhoods before returning to Grant Park, making it possible to watch from Downtown or head into the neighborhoods for a very different experience.

Plan transportation carefully. Organizers expect 55,000 participants, and streets along the course begin closing around 6 a.m., with impacts continuing into the afternoon. CTA is likely to be the easier way to move around many parts of the city Sunday.

2. Best Big City Day

When: Saturday, October 10; Riverwalk performance approximately 3:30–4:30 p.m.
Where: Chicago Riverwalk near City Winery, plus participating locations around the city
Admission: Riverwalk celebration is free; food and drinks sold separately

Chicago is celebrating its 10th consecutive year as Condé Nast Traveler's Best Big City in the U.S. by officially declaring October 10 “Best Big City Day.”

The centerpiece is a floating house-music party on the Riverwalk featuring pioneering Chicago DJ Lori Branch. Goose Island will also offer a limited “Perfect 10” beer, while Eli's Cheesecake is marking the milestone with a special cheesecake flight.

3. 10th Annual Lincoln Park Wine Fest

When: Friday, October 9, 5–10 p.m.; Saturday, 11 a.m.–10 p.m.; Sunday, 11 a.m.–7 p.m.
Where: Jonquil Park, 1001 W. Wrightwood Ave.
Admission: General admission starts around $30; VIP options available

Lincoln Park Wine Fest celebrates its 10th year with tasting sessions, food vendors, DJs and wines from producers around the world.

Tickets are organized into two-hour tasting windows, making this an easy event to pair with dinner or another stop in Lincoln Park. Proceeds support the Wrightwood Neighbors Association and local park initiatives.

4. Chicago Fashion Week

When: Thursday, October 8 through Sunday, October 18
Where: Multiple Chicago-area locations
Admission: Varies by event; some are free, others ticketed

Chicago Fashion Week kicks off this weekend with runway shows, shopping events, designer showcases and pop-ups spread across the city.

Now in its third year, the event highlights both established and emerging Chicago designers rather than concentrating everything in one venue. That makes this a good weekend to explore the schedule and choose an event that matches your style, whether that means runway fashion, streetwear or local shopping.

5. 53rd Annual Historic Pullman House Tour

When: Saturday, October 10 and Sunday, October 11, 11 a.m.–5 p.m.
Where: Pullman National Historical Park and surrounding historic Pullman neighborhood
Admission: $21 in advance through Oct. 8; $27 after; $22 seniors

One of Chicago's longest-running architecture events returns for its 53rd year, giving visitors rare access inside privately owned historic homes in Pullman.

The neighborhood's architecture tells the story of one of America's most significant planned industrial communities, so this is much more than a typical open-house tour. It is a chance to see how people actually live inside buildings that form part of a National Historical Park.

6. Chicago Zine Fest

When: Saturday, October 10, 11 a.m.–4 p.m.
Where: Harold Washington Library Center, 400 S. State St.
Admission: Free

Chicago Zine Fest celebrates its 15th year with nearly 100 independent publishers and artists filling the upper floors of Harold Washington Library.

Along with browsing and buying zines, visitors can try collage making, bookbinding, stamp making and other hands-on activities. This year's programming also includes an Indigenous Zinester Panel and a dedicated youth exhibitor area.

7. Glass Pumpkin Patch at The Morton Arboretum

When: Friday, October 9 through Sunday, October 11; shopping 11 a.m.–5 p.m. Friday and 10 a.m.–5 p.m. Saturday and Sunday
Where: The Morton Arboretum, 4100 Illinois Route 53, Lisle
Admission: Included with Arboretum general admission

More than 8,000 hand-blown glass pumpkins will fill The Morton Arboretum's West Lawn during one of DuPage County's most visually distinctive fall events.

Visitors can shop one-of-a-kind pumpkins while watching artists work with 2,000-degree molten glass during live glassblowing demonstrations throughout the weekend. The event also falls during the Arboretum's broader Fall Color Festival, so the grounds themselves are part of the attraction.

8. Fall Festival at Danada

When: Saturday, October 10 and Sunday, October 11, 11 a.m.–5 p.m.
Where: Danada Equestrian Center, 3S507 Naperville Road, Wheaton
Admission: Free; fees apply to some activities

One of the Forest Preserve District of DuPage County's largest annual events returns with trick riding, vaulting, carriage driving, horse demonstrations, family activities, food and live entertainment.

Visitors can also tour Danada's historic barn, once home to Kentucky Derby winner Lucky Debonair, and learn about horses, grooming and equestrian history. It is one of the best choices this weekend for families who want a full fall festival without a general admission charge.

9. Halloween Happening

When: Friday, October 9, 5:30–7:30 p.m.
Where: Ray Morrill Community Center, 1777 S. Blanchard St., Wheaton
Admission: Check the Wheaton Park District for current participation details

Halloween starts early in Wheaton with a costume-friendly evening designed for all ages.

The Wheaton Park District describes it as an activity-filled Halloween event, making it an easy Friday-night option for families who want seasonal fun before the larger Halloween weekends later in October.

10. OAKtoberfest

When: Saturday, October 10, 3–7 p.m.
Where: Lake Ellyn Park, Glen Ellyn
Admission: Free

Glen Ellyn's fall celebration puts the focus on one of Illinois' most important trees.

The free festival includes live music from School of Rock and The Fall Guys, guided oak-tree tours, games, face painting, hands-on art and a StoryWalk. Beer will also be available for adults, with a portion of sales supporting the Glen Ellyn Parks Foundation.

A Big Fall Weekend Across Chicagoland

If you are staying in Chicago, Marathon Sunday is the weekend's defining event, but Saturday may actually offer the widest variety with Best Big City Day, wine, fashion, architecture and Chicago Zine Fest all happening at once.

In DuPage, this is an especially strong weekend for fall activities. The Morton Arboretum, Danada, Wheaton and Glen Ellyn all have seasonal events on the calendar, giving families several options without heading into the city.

Before leaving home, check the linked official event page for weather updates, ticket availability, schedule changes and parking information, especially for outdoor events.

Exploring Chicago or DuPage This Fall?

The places people spend their weekends often reveal what they value in a community, whether that is walkability and major city events or parks, open space and suburban community festivals.

The Cory Tanzer Group at Option Premier helps buyers, sellers and relocating clients compare neighborhoods and communities throughout Chicago, the North Shore and the Western Suburbs based on both the housing market and everyday lifestyle.

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