There’s a raw energy in the air—a palpable, jittery anticipation as the old guard of hip-hop production gets tossed aside by the relentless force of technological innovation and cultural upheaval.

Chicago has one of the deepest hip-hop benches in the country. From the golden-era contributions of Common, Twista, and Lupe Fiasco to the global influence of Kanye West, the drill movement led by ...