Puerto Rican singer iLe, born Ileana Cabra Joglar, was once a rapper and singer in the political reggaeton group Calle 13, led by two of her brothers. But on her 2016 debut album, iLevitable, iLe applied her lush, stirring voice to old-school boleros, bugalú, and cha-chas about love and loss. Her 2019 release, Almadura, created after Hurricane Maria ravaged her home, offers powerful political messages about imperialism in Puerto Rico, along with vocals that sound as striking as her previous efforts. Where iLevitable showcased strings and horns, Almadura substitutes Afro Caribbean percussion, some dashes of electronic ambience, and an appearance by legendary pianist Eddie Palmieri. Oct. 1 at Howard Theatre. $39–$260.