
1. Rosalía
With another Album of Year win at the Latin Grammy Awards under her belt and her own limited edition Coca-Cola variant, it’s fair to say that Spanish singer-songwriter Rosalía is taking a victory lap this year. That includes headlining sets at no less than four foreign editions of Lollapalooza in Argentina, Chile, Brazil and Paris. With her schedule clear during early August, we’re nearly certain that she’ll add another Lolla to her itinerary and command a headlining slot in Grant Park.
Probability: 90 percent
Past Lollas: 2019