Multidisciplinary artist Keya Trammell won the $10,000 grand prize at the 2026 Chicago Made Music Showcase, held October 24 at the Chicago Cultural Center. The city’s Department of Cultural Affairs and Special Events also awarded cash prizes and 2027 performance slots at Lollapalooza and Taste of Chicago to other finalists from a field of 17.

Key Takeaways

• Keya Trammell won the $10,000 grand prize at the October 24 finale in the Chicago Cultural Center’s Claudia Cassidy Theater.
• Mike Lawry Baby and Luis Alfredo each received an additional $1,500 award.
• More than 150 artists auditioned, and 17 finalists performed for a panel of music industry professionals.
• Zion Ali and Zia Jenaye earned Chicago Made performance slots at Lollapalooza in 2027.
• Eight artists were selected to perform on a Taste of Chicago stage in 2027.
• Youth blues and funk group Knott Us Band will play the 2026 Chicago Christmas Tree Lighting Ceremony and the 2027 Chicago Blues Festival.

Keya Trammell Takes The 2026 Grand Prize

Keya Trammell walked away with the top prize after performing alongside 16 other finalists at the Chicago Made Music Showcase finale. The Chicago Department of Cultural Affairs and Special Events (DCASE) announced the results on October 27, naming Trammell, a multidisciplinary artist, as the winner of the $10,000 grand prize.

Two other performers also left with cash. Mike Lawry Baby and Luis Alfredo each received an additional $1,500 award for their performances.

The road to the finale was competitive. More than 150 Chicago musicians auditioned for this year’s showcase before the field was narrowed to the 17 artists who took the stage at the Claudia Cassidy Theater.

Winners Head To Lollapalooza And Taste Of Chicago In 2027

For many finalists, the prize that matters most is a stage. The Chicago Made Music Showcase connects local artists to some of the city’s highest-profile festivals, and the 2026 class will carry that opportunity into next year.

Zion Ali and Zia Jenaye were selected for Chicago Made performance opportunities at Lollapalooza in 2027. Eight artists earned places on a Taste of Chicago stage for the 2027 festival: Vee Armstrong, Tim Farrell, Huey Gang, Andrew Hoyt, Lima, Estefania Mena, JJ Smith and Smooie.

Knott Us Band, a youth blues and funk group, earned two separate opportunities. The group will appear at the 2026 Chicago Christmas Tree Lighting Ceremony and again at the 2027 Chicago Blues Festival.

Industry Judges Shape The Chicago Made Showcase

The Chicago Made Music Showcase is built to put emerging artists in front of people who work in the music business every day. This year’s panel included award-winning artist Sir the Baptist, entertainment lawyer Daryl Jones, Interscope/Capitol Records executive Caryn Lee, and music producer and writer Matt Hennessy. Bioncé Foxx hosted the evening.

That mix of performance, legal, label and production experience gives finalists more than a scorecard. For artists still building a career, a single night in front of the panel can open conversations that would be hard to start any other way. Prizes can also include career development consultations alongside cash and performance slots.

DCASE Commissioner Kenya K. Merritt described the showcase as “one way we’re helping local artists take their careers to the next level,” pointing to industry connections, professional resources and appearances on major city stages as the program’s core benefits.

A Pipeline That Keeps Sending Chicago Musicians To Bigger Stages

The clearest measure of the Chicago Made Music Showcase is what happens after the finale. The program has a track record of moving local artists from a 200-seat theater to festival crowds, and several names in the 2026 results show that pipeline at work.

Last year’s grand prize went to indie-jazz vocalist Mara Love, and the 2025 class sent Corr Kendricks and Free Joel Band to a Chicago Made showcase slot at Lollapalooza in 2026. M.E.H. won the grand prize in 2024, and Jasmine Marthel took it in 2023.

Some of this year’s honorees have been here before. Mike Lawry Baby, one of the 2026 cash award recipients, earned a 2025 Lollapalooza showcase performance through the 2024 competition. Zia Jenaye, now headed to Lollapalooza, earned a 2025 Taste of Chicago opportunity the same year. Their return shows how artists use the showcase as a repeated step in a longer climb rather than a one-time contest.

For Chicago’s music scene, that continuity matters. Each year’s results give audiences an early look at performers they may later see at Grant Park, at Taste of Chicago or at neighborhood events across the city.

How Chicago Made Supports Local Artists Year-Round

The showcase is one part of Chicago Made, a DCASE program that supports local creatives, entrepreneurs and artisans and promotes Chicago as both an artistic and economic hub. DCASE runs the music competition in partnership with Next Showcase USA, a Chicago nonprofit that helps emerging artists grow their careers.

The Chicago Cultural Center serves as the program’s home base, hosting the finale in its Claudia Cassidy Theater at 78 E. Washington St. Artists and audiences who want to stay connected to that space can explore the Cultural Center’s free fall and winter season, which continues DCASE’s focus on creative workers through the coming months.

FAQs

Who Won The 2026 Chicago Made Music Showcase?

Multidisciplinary artist Keya Trammell won the $10,000 grand prize. Mike Lawry Baby and Luis Alfredo each received an additional $1,500 award.

What Is The Chicago Made Music Showcase?

It is an annual competition run by the Chicago Department of Cultural Affairs and Special Events with Next Showcase USA. Chicago musicians audition, and finalists perform for a panel of music industry professionals.

What Do Chicago Made Music Showcase Winners Receive?

The grand prize winner receives $10,000. Other winners can earn cash awards, career development consultations and performance slots at events such as Lollapalooza and Taste of Chicago.

Where Was The 2026 Chicago Made Music Showcase Held?

The finale took place on October 24, 2026, in the Claudia Cassidy Theater at the Chicago Cultural Center, 78 E. Washington St.

Who Are Past Chicago Made Music Showcase Winners?

Recent grand prize winners include Mara Love in 2025, M.E.H. in 2024 and Jasmine Marthel in 2023.