Old Town Oktoberfest

Details

Friday, September 18, 2026 | 5pm to 10pm
Saturday, September 19, 2026 | 11:30am to 10pm
Sunday, September 20, 2026 | 11:30am to 8pm
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Overview

This fall, history and celebration come together at the 2nd annual Old Town Oktoberfest, happening Friday to Sunday, September 18-20. Old Town, Chicago’s very first German neighborhood, will come alive with the sights, sounds, and flavors of Bavaria in a brand-new tradition you won’t want to miss.

🍺 Authentic Flavors: Feast on bratwurst, pretzels, and classic German beers.
🎶 Lively Entertainment: Dance and sing along with traditional German bands, local favorites, and festival performers all weekend.
🏈 Big-Screen Football & Games: Catch the action on a giant outdoor screen and test your strength in Masskrugstemmen (stein-holding contests) for a chance to win prizes.

Whether you’re here for the food, the music, or simply to raise a glass with friends, Old Town Oktoberfest is set to become Chicago’s newest fall tradition.

The event is hosted by the Old Town Merchants & Resident Association.  For updated information on this year’s Old Town Oktoberfest, including schedule, music lineups, vendors, and directions, see below.


We’re working hard on this year’s entertainment line-up.  We’ll spill the tea soon but in the meantime, check out who we had in 2025:

Friday
6:00pm – Four Star Brass Band
8:15pm – Dancing Queen: An ABBA Salute

Saturday 
1:30pm – Live Band Karaoke (where you become the star!)
4:00pm – Four Star Brass Band
6:00pm – Rosie & The Rivets 
8:00pm – Super Creeps: The Music of David Bowie 

Sunday
2:00pm – Die Musikmeisters
3:30pm – Recorded Music
4:00pm – Big City Nights (Scorpions Tribute)
6:00pm – Stache

Looking to connect with active consumers at this event? For pricing and a customized benefits package, please contact Karyn Terrones at karyn@chicagoevents.com or 773-584-6625.

Coming soon!

The Old Town Merchants & Residents Association (OTMRA) is a Chamber of Commerce and Community Development non-profit organization that connects businesses, residents, and cultural organizations. Its mission is to support Old Town’s evolution as a vibrant location to live, work and laugh. For more info, visit oldtownchicago.org

OTMRA also holds the annual Wells Street Art Festival wellstreetartfest.us annually on the second weekend of June.

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