
One of Chicago's biggest fall festivals just got even better.
Y2K is excited to make our St. Al's Oktoberfest debut, taking over the Southport Main Stage from 6:00 PM–7:30 PM before Chicago favorites 16 Candles headline the evening from 8:00 PM–10:00 PM.
Spend the day enjoying one of Chicago's premier Oktoberfests featuring great food, cold drinks, live entertainment, and one of the city's best neighborhood festival atmospheres.
📅 Saturday, September 26, 2026
📍 St. Alphonsus Parish
1429 W. Wellington Ave.
Chicago, IL 60657
🎶 Y2K: 6:00–7:30 PM
🎸 16 Candles: 8:00–10:00 PM
For decades, St. Al's Oktoberfest has been one of Chicago's favorite neighborhood festivals, bringing together incredible live music, delicious food, Oktoberfest traditions, local vendors, and one of the city's best street festival atmospheres.
Whether you're coming for the music, the food, or the beer, it's the perfect way to spend a fall Saturday in Chicago.
Whether you grew up with cassette tapes, CDs, Napster, TRL, or your first iPod...
This night has your soundtrack.
Y2K delivers the biggest hits from the late 90s and early 2000s with a high-energy live show packed with singalongs, pop-punk favorites, alternative rock, hip-hop, pop, and party anthems.
After a short stage change, Chicago favorites 16 Candles take over with the biggest songs of the 80s.
Come early.
Stay all night.
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