Alessia Cara + Eryn Allen Kane

Canadian pop singer Alessia Cara got her start doing acoustic cover songs on YouTube before she was discovered and signed to Def Jam Recordings—a typical millennial success story. Her 2015 debut, Know-It-All, demonstrated her R&B chops, but it's her vocals on the Lin-Manuel Miranda-penned "How Far I'll Go" (from Disney's Moana) that you're most likely to recognize. During her performance at Taste of Chicago, she's joined by Chicago vocalist Eryn Allen Kane, who developed her soulful pipes singing in church.