Chiesa began his youth career with U.S. Settignanese from Settignano, (a frazione northeast of Florence), it was here that he had the privilege of visiting the Museo del calcio in Coverciano; the Azzurris Museum of Football and also where Fiorentina legend Kurt Hamrin coached the Settignano youth players [REF].
He made his competitive debut for Fiorentina in a 2-1 away defeat against Juventus, during the opening fixture of the 2016-17 Serie A season.