Things to Do in Chicago and DuPage This Weekend: September 25–27, 2026
CHICAGO— The first weekend of fall is packed with reasons to get outside.
From the Hyde Park Jazz Festival and World Music Festival to Oktoberfest celebrations, food festivals and the opening weekend of Lincoln Park Zoo's Fall Fest, Chicago has a particularly busy calendar. Out in DuPage County, the Presidents Cup at Medinah, Cantigny's Fall Fest and two major family-friendly fall celebrations give suburban residents plenty of options too.
Here are 10 events happening Friday, September 25 through Sunday, September 27, 2026.
1. World Music World Music Festival Chicago
When: Friday, September 25 through Sunday, October 4; multiple times
Where: Multiple Chicago locations
Admission: Free
Chicago's citywide World Music Festival begins Friday with more than 50 artists and groups appearing throughout its 10-day run. Opening weekend starts with Ragamala, an overnight celebration of Indian classical music at the Chicago Cultural Center from 6 p.m. Friday until 8 a.m. Saturday.
Saturday brings music to Ping Tom Memorial Park from 1 to 7 p.m., while Sunday's schedule includes a free From Bomba to Salsa performance along the Chicago Riverwalk at 2 p.m. It is one of the strongest choices this weekend if you want live music without buying a festival ticket.
2. Chicago Gourmet
When: Friday, September 25 through Sunday, September 27
Where: Harris Theater Rooftop, Millennium Park and participating Downtown venues
Admission: Ticket prices vary by event
Chicago Gourmet continues through Sunday with a weekend built around some of the city's biggest chefs, restaurants, wines and spirits. Friday's Hamburger Hop runs from 6 to 9 p.m., Saturday features two Grand Cru sessions, and Rise & Shine Gourmet closes the weekend Sunday from noon to 3 p.m.
3. 20th Annual Hyde Park Jazz Festival
When: Saturday, September 26 and Sunday, September 27
Where: Multiple venues throughout Hyde Park
Admission: Free; $10 donation encouraged
One of Chicago's best free music weekends returns for its 20th anniversary, spreading jazz performances across indoor and outdoor venues throughout Hyde Park. The 2026 lineup includes Joshua Redman, Nicole Mitchell's Black Earth SWAY, Kris Davis Trio, Alfredo Rodriguez Quintet featuring Pedrito Martinez, Tomeka Reid and the HPJF 20th Anniversary Band.
Because performances happen throughout the neighborhood, this is an event worth planning before you arrive. The festival's official program includes the schedule, venue information, maps and transit details.
4. St. Al's Oktoberfest
When: Friday, September 25, 5–10 p.m.; Saturday, noon–10 p.m.; Sunday, noon–7 p.m.
Where: St. Alphonsus Church, 1429 W. Wellington Ave.
Admission: $10 Friday and Saturday; $5 suggested donation Sunday
Chicago's longtime Lakeview Oktoberfest returns with German food, beer gardens, stein-hoisting competitions and live entertainment across multiple stages.
Friday's lineup includes Dancing Queen: An ABBA Salute and Rod Tuffcurls & The Bench Press, while 16 Candles headlines Saturday night. Sunday shifts toward family programming with Kinderfest and the ceremonial tapping of a root beer keg.
5. Sabor Fest
When: Friday, September 25, 5–10 p.m.; Saturday and Sunday, noon–10 p.m.
Where: 18th Street and Halsted Street, Pilsen
Admission: $5 suggested donation
Sabor Fest returns to Pilsen with three days of food, local vendors, art, music and neighborhood businesses centered around 18th and Halsted.
A new addition this year is the festival's Rave Edition, which combines regional Mexican music with EDM, DJs and rave-inspired production. The festival is open to all ages, making it an easy option for spending part of the day exploring Pilsen before staying for the evening entertainment.
6. Fall Fest at Lincoln Park Zoo
When: Friday, September 25 through Sunday, September 27, 10 a.m.–5 p.m.
Where: Lincoln Park Zoo
Admission: Free; some rides and activities are ticketed
Fall Fest opens this weekend at Lincoln Park Zoo with pumpkins, s'mores, seasonal food, decorated gardens, rides and fall-themed animal enrichment.
Professional pumpkin carving is scheduled Saturdays and Sundays from 10 a.m. to 1 p.m., and ticketed attractions include a Ferris wheel, giant slide and inflatables. General entry to both the zoo and Fall Fest remains free.
7. 2026 Presidents Cup at Medinah
When: Friday, September 25 through Sunday, September 27
Where: Medinah Country Club, Medinah
Admission: Ticketed; prices vary by day and package
One of professional golf's biggest international team events is happening in DuPage County this weekend.
The United States Team, captained by Brandt Snedeker, faces Geoff Ogilvy's International Team at Medinah Country Club. Friday is Day 2 of competition, Saturday is Day 3 and Sunday's final round determines the overall result.
Tickets remain listed through the official Presidents Cup site, although availability varies by day and hospitality level. Even for people who do not normally follow golf, this is one of the most significant sporting events Chicagoland will host this year.
8. Celebración de los Árboles
When: Saturday, September 26 and Sunday, September 27; festival programming throughout the day
Where: The Morton Arboretum, Lisle
Admission: Included with Arboretum general admission
The Morton Arboretum celebrates Latin American culture and its connections to nature with live music, dance, traditional food, artisans, tours and family activities.
One of the highlights is live Lucha Libre, with matches taking place Saturday and Sunday and a championship ceremony Sunday afternoon. The weekend also includes mariachi, ballet folklórico, salsa and bachata lessons, Spanish-language tram tours and food ranging from tamales and empanadas to paletas and conchas.
9. Cantigny Fall Fest
When: Saturday, September 26 and Sunday, September 27, 10 a.m.–4 p.m.
Where: Cantigny, 1S151 Winfield Road, Wheaton
Parking: $21 per car
Cantigny is going all-in on the first weekend of fall with a two-day festival featuring a seasonal market, food trucks, live music and guided garden tours.
Families will also find crafts, bounce houses and a petting zoo, making this one of the stronger all-ages choices in the western suburbs this weekend. Live music runs during the day in multiple areas of the park.
10. Harvest Fest at Fischer Farm
When: Saturday, September 26, noon–5 p.m.
Where: Fischer Farm, 16W680 Old Grand Ave., Bensenville
Admission: Free; food and some activities require tickets
For a more traditional fall afternoon, Fischer Farm's annual Harvest Fest returns with live music, seasonal activities, arts and crafts, food and family entertainment.
The event also features an Artisan Alley with nearly 30 local vendors, plus free activities around the historic farm property. Admission is free, while tickets used for certain activities, food and beverages cost $1 each and are sold in groups of five.
A Busy First Weekend of Fall in Chicagoland
This weekend is a good example of how different fall can look depending on where you live in Chicagoland.
You can spend Saturday moving between music stages in Hyde Park, eat your way through a festival Downtown, head to Pilsen for Sabor Fest, or trade the city for gardens, golf and traditional fall events in Lisle, Wheaton, Medinah and Bensenville.
As always with outdoor events, schedules and ticket availability can change, so check the linked official event page before heading out.
Exploring Chicago or the Western Suburbs This Fall?
Where people spend their weekends often says a lot about where they eventually want to live. Access to restaurants, parks, festivals, transit and community events can matter just as much as square footage when comparing neighborhoods and suburbs.
The Cory Tanzer Group at Option Premier helps buyers, sellers and relocating clients compare communities throughout Chicago, the North Shore and the Western Suburbs with local market knowledge that goes beyond the listing itself.
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