Old Town Oktoberfest

Details

Friday, September 18, 2026 | 5pm to 10pm
Saturday, September 19, 2026 | 11:00am to 10pm
Sunday, September 20, 2026 | 11:00am to 8pm
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Overview

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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.


Friday
5:30pm – Recorded Music / Stein Holding Competition #1
6:00pm – Four Star Brass Band
7:15pm – Stein Holding Competition #2
8:00pm – Hello Weekend

Saturday
11:00am – Apasionado Duo
12:00pm – Four Star Brass Band
1:15pm – Stein Holding Competition #1
1:45pm – Second Hand Soul Band
3:15pm – Stein Holding Competition #2
3:45pm – RAVIV
5:00pm – Stein Holding Competition #3
5:30pm – Run Forrest Run
7:00pm – Stein Holding Competition #4
7:45pm – Funky Monks: Red Hot Chili Peppers Tribute

Sunday
12:30pm – School of Rock
1:30pm – Stein Holding Competition #1
2:00pm – Bratwurst Brothers
3:15pm – Stein Holding Competition #2
3:45pm – Live Band Karaoke
5:15pm – Stein Holding Competition #3
5:45pm – 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.

 

Vending Applications

 

Please note that all applications are subject to acceptance and availability.

We do not provide guaranteed exclusivity to any participant/exhibitor or category. We work on a first come first serve basis when approving vendors. We would highly recommend everyone apply as early as possible. Do not wait until the last minute as sometimes the event will be completely booked and applications will close earlier than the deadline.

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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