Chiesa began his youth career with U.S. Settignanese from Settignano,, where he was coached by Fiorentina legend Kurt Hamrin.
Fiorentina
He joined Fiorentina in 2007. Initially a member of their Giovanili side, Chiesa was assigned to the under-19 squad for the :it:Campionato Primavera 2014-2015|2014–15 season, and scored a single goal in seven appearances for their Primavera side. The following season, he made 23 appearances and scored seven goals. Chiesa signed his first professional contract with Fiorentina in February 2016. 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. Fiorentina manager Paulo Sousa opted to replace him at half-time with loan signing Cristian Tello. On 29 September, Chiesa made his Europa League debut in Fiorentina's 5–1 home win over Qarabağ. On 8 December, he marked his fourth Europa League appearance by scoring his first ever senior goal in a 1–2 away victory over Qarabağ; he was later sent off during the same match for a double booking. On 15 January 2017, Chiesa appeared to score the match-winner in a 2–1 home win over rivals Juventus, from a Milan Badelj pass; however, the goal was assigned to Badelj, as, following review, the replays did not confirm whether Chiesa had deflected the pass. Later that month, Chiesa extended his contract with Fiorentina until 30 June 2021. On 21 January, he scored his first goal in Serie A in a 3–0 away victory over Chievo. Just eight days later, Chiesa scored his second league goal in a 3–3 home draw against Genoa. On 7 May, he netted the opening goal for Fiorentina in an eventual 2–2 draw against Sassuolo; this being his third goal for the club, and his first in Serie A in nearly four months. The goal came just four minutes after teammate Nikola Kalinić's penalty miss just after the half-hour mark. On 16 September, the following season, Chiesa marked his 30th league appearance for Fiorentina with a goal in the Derby dell'Appennino against Bologna; scoring the opener in the 51st minute of the game, in an eventual 2–1 home win. On 30 January 2019, Chiesa scored a hat-trick in the 7–1 home victory over Roma in the quarter-final match of the Coppa Italia.
International career
Chiesa was first called-up to the Italy U19 squad back in 2015. He along with fellow Fiorentina teammate Simone Minelli were selected as part of Paolo Vanoli's preliminary 27-man squad for the 2016 UEFA Euro Under-19 Championship in Germany. Chiesa played for Italy U19s in friendlies against the Czech Republic, Spain and France. In 2016, he received a call-up from Italy U20s' Alberigo Evani to represent the side at the 2015–16 Under-20 Four Nations Tournament. In March 2017, Chiesa was called up by Italy U21s' boss Luigi Di Biagio to represent the Azzurrini in friendlies against Poland and Spain. He made his debut with the Italy U21 team on 23 March 2017, in a 1–2 victory against Poland. Chiesa provided the assist to Lorenzo Pellegrini's opener. He retained his place in the starting line-up against Spain in a 1–2 defeat at the Stadio Olimpico. Despite only being called up to the under-21 side back in March 2017, Chiesa was selected by Italy's senior head coach Gian Piero Ventura for the team's unofficial friendly against San Marino in Empoli on 31 May. Chiesa made his unofficial senior international debut in the match, starting in Italy's eventual 8–0 win. In June 2017, he was included in the Italy under-21 squad for the 2017 UEFA European Under-21 Championship by manager Di Biagio. In Italy's opening match of the tournament on 19 June, he set-up Andrea Petagna's goal with a cross following a corner in a 2–0 win over Denmark. Italy were eliminated by Spain in the semi-finals on 27 June, following a 3–1 defeat. In March 2018, he was awarded his first official senior call-up to the Italian national team, under interim manager Di Biagio, for Italy's friendlies against Argentina and England later that month. On 23 March, he made his official senior international debut in the friendly against Argentina; Italy were defeated 2–0. He took part with the U21 team in the 2019 UEFA European Under-21 Championship held in Italy, where he scored three goals in the group stage phase. His first senior international goal came on 18 November, in a 9–1 home win over Armenia, in Italy's final Euro 2020 qualifier, under manager Roberto Mancini; he also assisted two goals during the match: Ciro Immobile's first goal, and Riccardo Orsolini's goal.
Style of play
Regarded as a promising young prospect, Chiesa is a talented, fast, skillful, and hardworking player, with good technique, a short stature, and a slender build. He usually plays as a right winger, a position which enables him to create goalscoring opportunities for teammates, especially by crossing a ball into the penalty box with his stronger right foot. He can also play on the left wing, cutting into the center to shoot on goal. Besides both wings, he has played in several central positions, most frequently as either an attacking midfielder or a second striker. In addition to his primary duties in attack, he often contributes to the defensive play by chasing the opposition's wingers down the flank to win back possession, and has been deployed occasionally as a right wing back in a 3–5–2 formation.
Personal life
Chiesa is the son of Enrico Chiesa, a former professional footballer who played for the likes of Cremonese, Sampdoria, Parma, Fiorentina, Lazio and Siena, and represented the Italian national team. He enrolled at the International School of Florence, where he frequently took lessons in learning English. Chiesa also spent two years at university, studying Sports Science.