Nation Chicago will elect first black female mayor; Lightfoot and Preckwinkle advance to runoff February 27, 2019 Aamer Madhani, USA TODAY Comments Off on Chicago will elect first black female mayor; Lightfoot and Preckwinkle advance to runoff Lori Lightfoot and Toni Preckwinkle are headed to an April 2 runoff to decide who will become the next mayor of the nation’s third-largest city.