September 25–27, 2026: Fall Festivals, Oktoberfests & Things to Do in The Near West Burbs and Chicago 🍂
- Paul Froiland
- 3 days ago
- 10 min read
September 25–27, 2026 | Oak Park, Western Suburbs & Chicago
The final weekend of September is absolutely packed.
Oktoberfest season is still going strong, but this weekend also brings live music, Latin food and culture, African and Caribbean music and food, chicken wings, family activities and one of Oak Park's biggest annual street festivals.
From Oaktoberfest just down the road in Oak Park to Oktoberfest Chicago, Sabor Fest in Pilsen and WingOut next to Wrigley Field, here are 8 festivals worth checking out September 25–27.
🍂 OAK PARK OAKTOBERFEST
Oak Park | September 25–26
One of the easiest picks of the weekend from Berwyn is also one of the best.
Oaktoberfest returns to Downtown Oak Park with two days of live music, food from local restaurants, craft beer and wine, plus family activities.
📍 Marion Street between Lake Street & North Boulevard
📅 Friday, Sept. 25 – Saturday, Sept. 26
🎟️ FREE
⏰ FESTIVAL HOURS
Friday: 4–10 PM
Saturday: Noon–10 PM
🎸 FRIDAY MUSIC
4:30–6 PM — RICO!
Latin rock with rock, reggae, soul and Afro-Cuban influences.
6:30–8 PM — Joanna Connor
Chicago blues and blues-rock.
8:30–10 PM — Shinyribs
Austin swamp-funk, soul, blues and roots music.
🎶 SATURDAY MUSIC
12:30–2 PM — School of Rock
Rock, pop and indie.
2:30–4 PM — Patrick Sweany
Nashville blues and roots rock.
4:30–6 PM — Rachel Swain
Americana.
6:30–8 PM — ¡ESSO! Afrojam Funkbeat
Latin funk, Afro-Caribbean rhythms, jazz and psychedelic rock.
8:30–10 PM — The Resolvers
Big-band reggae blending Jamaican roots and New Orleans influences.
👨👩👧 FAMILY FUN
Saturday also brings Oaktoberfest's popular Kids' Root Beer Garden, with family activities from local organizations and businesses.
🚆 GETTING THERE
This is another festival where leaving the car at home makes sense.
Take the Metra UP-West Line to Oak Park or the CTA Green Line to Harlem/Lake. Both put you within easy walking distance of the festival.
🍺 LA GRANGE OKTOBERFEST
La Grange | September 25–27
La Grange is launching a new three-day Oktoberfest right in the heart of downtown.
The German-themed street festival is being organized by the La Grange Business Association and is designed as a community celebration featuring local restaurants, businesses and nonprofits.
📍 Calendar Avenue between La Grange Road & Ashland Avenue
📅 Friday, Sept. 25 – Sunday, Sept. 27
⏰ FESTIVAL HOURS
Friday: 5–10 PM
Saturday: Noon–10 PM
Sunday: Noon–9 PM
Expect German-inspired food and drinks, live music, games and local businesses throughout the festival area.
🎸 MUSIC
Because this is a brand-new street festival debuting this year, the organizers have not yet published the specific hourly set times or the specific names of individual bands on their official schedule.
However, the festival's operating hours for live entertainment are locked in:
Friday, September 25: Live music from 5:00 PM – 10:00 PM
Saturday, September 26: Live music all day from 12:00 PM – 10:00 PM
Sunday, September 27: Live music all afternoon from 12:00 PM – 9:00 PM
🚆 GETTING THERE
This one is ridiculously easy by train.
Take the BNSF Line to La Grange Road Station. The festival is being held right in downtown La Grange, making Metra one of the easiest ways to get there.
🇩🇪 OKTOBERFEST CHICAGO AT ST. ALPHONSUS
Lakeview | September 25–27
If you're looking for the classic Chicago neighborhood Oktoberfest experience, this is one of the biggest options of the weekend.
St. Alphonsus Oktoberfest combines German food and beer with two stages of live music, stein-holding competitions and a family-focused Kinderfest on Sunday.
📍 St. Alphonsus Church — 1429 W. Wellington Ave., Chicago
📅 Friday, Sept. 25 – Sunday, Sept. 27
⏰ FESTIVAL HOURS
Friday: 5–10 PM
Saturday: Noon–10 PM
Sunday: Noon–7 PM
🎸 FRIDAY — SOUTHPORT MAIN STAGE
6–7:30 PM — Dancing Queen: An ABBA Salute
7:50 PM — Ceremonial Keg Tapping & Official Blessing of the Beer
8–10 PM — Rod Tuffcurls & The Bench Press
🍺 FRIDAY — BIERGARTEN STAGE
5–6 PM — Four Star Brass Band
6:30–7:30 PM — The Divas
8–10 PM — The Birkenrocks
🎸 SATURDAY — SOUTHPORT MAIN STAGE
2–3:30 PM — Viceroy
4–5:30 PM — The Wild Chicago
6–7:15 PM — Y2K
7:15–8 PM — Sam Adams Stein Holding Competition
8–10 PM — 16 Candles
🍺 SATURDAY — BIERGARTEN STAGE
2:30–4 PM — School of Rock
4:30–5:30 PM — Four Star Brass Band
5:30–6 PM — Mr. & Mrs. Oktoberfest
6–7:30 PM — Live Band Karaoke
8–10 PM — Wedding Banned
👨👩👧 SUNDAY — KINDERFEST
Sunday becomes the family day.
The festivities begin with the Kinderfest opening ceremonies, followed by a ceremonial tapping of a keg of root beer at 12:15 PM.
St. Alphonsus is also hosting its Battle of the Bands Sunday.
Additional Sunday performance slots were still listed as TBD when we published this guide.
Football will be shown on the Biergarten jumbotron.
🍺 STEIN HOLDING
Think you can hold a full stein longer than everyone else?
Preliminary stein-hoisting rounds take place throughout the festival, leading to the finals Saturday evening.
🚆 GETTING THERE
CTA is your friend here.
The Wellington Brown/Purple Line station is within walking distance of St. Alphonsus. The neighborhood is also served by several CTA bus routes.
Parking in Lakeview during a festival weekend can be a headache. We'd take the train.
🌮 SABOR FEST
Pilsen | September 25–27
Sabor Fest takes over 18th & Halsted for three days celebrating the food, music, artists, businesses and culture that make Pilsen one of Chicago's most interesting neighborhoods.
And there's something new this year.
The festival is introducing a Rave Edition, combining regional Mexican music with EDM, DJs and rave-inspired production after dark.
📍 18th Street & Halsted Street — Pilsen
📅 Friday, Sept. 25 – Sunday, Sept. 27
🎟️ $5 suggested donation
👨👩👧 All ages
⏰ FESTIVAL HOURS
Friday: 5–10 PM
Saturday: Noon–10 PM
Sunday: Noon–10 PM
Expect food and drink vendors, merchandise, local art, live entertainment and businesses and creatives from around Chicago.
🎧 MUSIC
Music Programming Highlights
The "Rave Edition": New for 2026, the evening music programming features a special cross-genre blend.
Genre Fusion: The music blends traditional Regional Mexican music with modern electronic beats, EDM, and live DJs.
Production: The nighttime performances will feature rave-inspired stage production and visuals.
Daytime Music: Traditional live music, local Chicago artists, and cultural entertainment will perform during the daytime hours before the electronic fusion starts after dark.
🚆 GETTING THERE
CTA is the easiest option.
The Pink Line 18th Street station gets you into Pilsen, followed by a walk east toward Halsted. CTA buses along the 18th Street corridor are another option.
🌍 AFRICAN/CARIBBEAN INTERNATIONAL FESTIVAL OF LIFE + JERK, SEAFOOD & VEGAN FESTIVAL
Chicago | September 25–27
This is easily one of the most culturally diverse festivals on our September list.
The 33rd African/Caribbean International Festival of Life joins forces with the 10th Anniversary Jerk, Seafood & Vegan Festival for three days celebrating African and Caribbean music, food, art and culture.
📅 Friday, Sept. 25 – Sunday, Sept. 27
⏰ Noon–10 PM daily
🎟️ Standard one-day admission listed at $35
👧 Children under 12 FREE with an adult
Advance promotional tickets may be available for less.
🎶 MUSIC & ENTERTAINMENT
The organizer has announced more than 30 acts are expected across the festival.
Among the artists already announced are legendary reggae groups:
Chalice
Big Mountain
Additional artists and the complete day-by-day Unity Stage schedule are still being announced.
Expect reggae, Caribbean music, international performers, cultural showcases and other live entertainment throughout the weekend.
🍗 COME HUNGRY
Food is a huge part of this festival.
Expect:
🔥 Authentic jerk dishes
🦐 Seafood
🌱 Vegan options
🌴 Caribbean specialties
🌍 International cuisine
There will also be vendors, shopping, cultural programming and family-friendly activities.
⚠️ LOCATION UPDATE
Union Park - 1501 W Randolph St
🍗 WINGOUT CHICAGO
Gallagher Way | September 26–27
Wings.
Lots and lots of wings.
WingOut Chicago returns for its 11th year, bringing some of Chicago's best wing spots together for a two-day outdoor food festival at Gallagher Way next to Wrigley Field.
📍 Gallagher Way — 3635 N. Clark St., Chicago
📅 Saturday–Sunday, Sept. 26–27
🎟️ Ticketed event — multiple sessions
Expect everything from classic Buffalo wings to smoked, jerk, honey chili, sweet-and-spicy and plenty of other variations.
🍗 HOW IT WORKS
There are several ticket options.
GENERAL ADMISSION
Gets you into your selected WingOut session with access to the wing vendors, bars, competitions and live entertainment.
Food and drinks are purchased separately.
VIP EXPERIENCE
Includes early entry, unlimited wings from participating restaurants and an included sponsored drink package.
VIP + BALCONY
Includes the VIP experience plus second-level balcony and lounge access, additional snacks, seating, restrooms and an extended balcony drink package.
Ticket prices vary by session and increase as the event approaches.
Walk-up admission may be available, but the organizer says entry isn't guaranteed if sessions reach capacity.
🎶 LIVE MUSIC
WingOut will feature Soul, R&B and Reggae throughout the weekend.
🏆 WING COMPETITION
This isn't just eating.
Attendees get to sample wings from restaurants around Chicago while competitors battle for bragging rights, with judging and crowd voting helping determine some of the city's best wings.
🚆 GETTING THERE
Take the CTA Red Line to Addison.
Gallagher Way sits immediately beside Wrigley Field, making this another event where taking the train is considerably easier than trying to park in Wrigleyville.
🍺 ROSETOBER FEST
Rosemont | September 26
Rosemont gets into Oktoberfest season with a free six-hour celebration at Parkway Bank Park.
This is a compact one-day event with authentic German music, dancing, competitions, food and even live wood carving.
📍 Parkway Bank Park — 5501 Park Place, Rosemont
📅 Saturday, Sept. 26
⏰ Noon–6 PM
🎟️ FREE
🇩🇪 COMPLETE SCHEDULE
12–6 PM — Paloma
Live authentic German music throughout the festival.
2 PM — German Dancing
Society of Danube Swabians Youth Group.
3 PM — Stein Hoisting Competitions
Separate men's and women's rounds, with winners receiving venue gift cards.
4 PM — German Dancing
Society of Danube Swabians Youth Group returns.
5 PM — Couples Pretzel Lanyard Game
There will also be live wood carving during the festival.
🥨 FOOD & DRINK
Restaurants throughout Parkway Bank Park will be selling food and drinks, including their own spins on German-inspired festival dishes along with regular menu favorites.
Outside food, beverages and coolers aren't permitted.
Picnic tables will be available, and guests can bring their own chairs or blankets.
🚆 GETTING THERE
Rosemont is accessible via both CTA and Metra.
The Rosemont CTA Blue Line station gets you into the area, while the Rosemont Metra station is also nearby. Depending on which you use, expect a walk or local connection to Parkway Bank Park.
If you're driving, parking can be validated for free at participating Parkway Bank Park venues.
🍺 HIGHLAND PARK OKTOBERFEST
Highland Park | September 26
Highland Park brings Oktoberfest to a new location this year in the Ravinia District.
It's only four hours long, but they've packed a surprising amount into the afternoon Bavarian dancers, German music, a country headliner, games, beer, food and family entertainment.
📍 Jens Jensen Park — 540 Roger Williams Ave., Highland Park
📅 Saturday, Sept. 26
⏰ 4–8 PM
🎶 COMPLETE ENTERTAINMENT SCHEDULE
4–4:15 PM — Bavarian Dancers
4:15–5:45 PM — Alpine Thunder
5:30–6 PM — Bierstein Contest
6–8 PM — Icons of Country
🎯 ACTIVITIES
The park will also feature:
🍺 Bier Hall tent
🔨 Hammerschlagen
💪 High striker
🥨 Pretzel necklaces
🪓 Axe throwing
🏈 Fowling — football meets bowling
🌽 Cornhole
⭕ Ring games
📸 Photo opportunities
Kids can also meet Snow White, Rapunzel and Flynn Rider.
Food and beverages will be available from participating area businesses.
🚆 GETTING THERE
This one is surprisingly Metra-friendly.
Take the UP-North Line to Ravinia Station. The station is right in the Ravinia Business District near Roger Williams Avenue and Jens Jensen Park.
The city is specifically encouraging visitors to use Metra, walk or bike.
Free parking is also available for those driving.
🍂 SO, WHERE ARE WE GOING?
Eight festivals. Very different experiences.
🎸 BEST LIVE MUSIC: OAKTOBERFEST
The combination of Joanna Connor, Shinyribs, Patrick Sweany, ¡ESSO! and The Resolvers gives Oak Park one of the most interesting overall music lineups of the weekend.
🍺 BEST BIG CHICAGO OKTOBERFEST: ST. ALPHONSUS
Two stages, three days, German food and beer, stein competitions, Kinderfest and a Saturday night featuring 16 Candles and Wedding Banned.
🌮 BEST FOR SOMETHING DIFFERENT: SABOR FEST
Pilsen food and culture plus the brand-new regional-Mexican-meets-EDM Rave Edition.
🌍 BEST CULTURAL FESTIVAL: INTERNATIONAL FESTIVAL OF LIFE
African and Caribbean culture, reggae and international music plus an entire Jerk, Seafood & Vegan Festival.
🍗 BEST FOOD MISSION: WINGOUT CHICAGO
Go hungry.
Very hungry.
👨👩👧 BEST FAMILY OKTOBERFEST: HIGHLAND PARK
Bavarian entertainment for the adults with plenty of games and character meet-and-greets for kids.
🇩🇪 BEST TRADITIONAL AFTERNOON: ROSETOBER FEST
German band, German dancers, stein hoisting and food in one free six-hour festival.
⭐ IF WE WERE PLANNING THE WEEKEND...
If we could only pick one festival each day, here's how we'd do it.
🍂 FRIDAY — OAKTOBERFEST
Start close to home in Oak Park.
Grab some food, then make the evening about the music:
🎸 4:30 PM — RICO!
🎸 6:30 PM — Joanna Connor
🎸 8:30 PM — Shinyribs
Free admission, good food and a genuinely strong music lineup.
Our Friday pick: Oaktoberfest.
🇩🇪 SATURDAY — OKTOBERFEST CHICAGO
Saturday night belongs to St. Alphonsus.
Go later in the afternoon and catch:
🎸 4 PM — The Wild Chicago
🎸 6 PM — Y2K
🍺 7:15 PM — Stein Holding Competition
🎸 8 PM — 16 Candles
Or head over to the second stage for Wedding Banned from 8–10 PM.
Our Saturday pick: Oktoberfest Chicago.
🌮 SUNDAY — SABOR FEST
After two days of fall festivals and Oktoberfest, do something completely different.
Head to Pilsen for local food, artists, vendors, music and the new Sabor Fest Rave Edition.
Eat. Walk around Pilsen. Catch some music. Make an afternoon and evening of it.
Our Sunday pick: Sabor Fest.
🍂 SEPTEMBER IS ALMOST OVER — BUT FALL ISN'T
September 25–27 closes out an incredible month of festivals around Berwyn, the western suburbs and Chicago.
But we're nowhere near finished.
October brings another round of Oktoberfests, pumpkin festivals, fall celebrations and Halloween events and we'll keep adding the best ones to the Discover Berwyn Fall Festival Guide.
🍂 Looking for More Fall Festivals?
Subscribe to the Berwyn Insider newsletter and never miss what's happening around Berwyn and the western suburbs.
Save the guide. Send it to a friend. Pick a festival.
Live here. Explore everywhere.
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🔗 SOURCES & OFFICIAL EVENT INFORMATION
Event dates, schedules, admission and festival details were compiled from official organizers and event websites. Festival information can change, so always check the official event page before heading out.
🍺 La Grange Oktoberfest — La Grange Business Association / official event information
🇩🇪 Oktoberfest Chicago at St. Alphonsus — official Oktoberfest Chicago event information
🌮 Sabor Fest — Pilsen — official event information
🌍 International Festival of Life + Jerk, Seafood & Vegan Festival — the JSVFest site confirms Union Park for Sept. 25–27.
