The Outlaw Music Festival Chicago brings country, folk, and Americana music to Chicago, Illinois on August 25, 2026, headlined by legendary Willie Nelson & Family alongside The Avett Brothers. The lineup features a mix of established and emerging American artists including Lukas Nelson, Sierra Hull, Don Was & the Pan-Detroit Ensemble, and Stephen Wilson Jr, spanning genres from traditional country and folk to folk rock. This single-day festival celebrates the outlaw country tradition with a curated selection of artists representing the best of contemporary American roots music.

Outlaw Music Festival Chicago is a one-day standalone music festival.