Dillo 2019 happened on June 1, 2019. The lineup was stacked with Main Stage performers Hippo Campus, Teyana Taylor, Anna Lunoe, Daya, and A$AP Ferg, Second Stage performers Monique Heart*, Kota the Friend*, DFree Da Vinci*, Caleborate, and Amindi, and student performers/winners of Battle of the Bands and Battle of the DJs, respectively, FIZZ and Luminosity* making this the first predominantly-female Dillo lineup in the festival's history. Additionally, this was the first ever themed Dillo Day. The selected theme "Retro" was integrated into all aspects of the festival including the development of promotional materials and day-of programming including a live mural that was created under commission by Chicago-based artist Afrokilla and other experiential art projects brought to the lakefill by a number of student artists.
* = artist was unable to perform or had their set disrupted due to weather