His father, Enrico, was also a professional footballer; he played for various Serie A clubs, most notably Parma, Fiorentina and Siena, and represented the Italy national team.

[7] Chiesa began his youth career with Settignanese from Settignano, a frazione northeast of Florence, where he was coached by Fiorentina legend Kurt Hamrin.

[12] 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.

[19] On 16 September 2017, in the 2017–18 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.

[20] On 30 January 2019, during the 2018–19 season, Chiesa scored a hat-trick in the 7–1 home victory over Roma in the quarter-final match of the Coppa Italia.

[22] On 17 October, Chiesa made his debut for Juventus, providing an assist for Álvaro Morata and getting a straight red card in a 1–1 away draw to Crotone.

[34] On 2 November 2022, after nearly ten months out of action, Chiesa made his season debut in a 2–1 home defeat against Paris Saint-Germain, replacing Fabio Miretti in the 74th minute, in their final 2022–23 UEFA Champions League match.

[39] Chiesa provided his first assist in an EFL Cup match against West Ham United on 25 September to Diogo Jota.

[citation needed] He was selected as part of Paolo Vanoli's preliminary 27-man squad for the 2016 UEFA European Under-19 Championship in Germany.

[43] 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.

[citation needed] Despite only being called up to the under-21 side 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.

[58][59] In the semi-final against Spain on 6 July, he scored the opening goal in a 1–1 draw; a game in which Italy advanced to the final of the tournament after extra time following a 4–2 penalty shoot-out victory.

[60] On 11 July, Chiesa suffered an injury late in the second half of regulation time in the UEFA Euro 2020 Final against England at Wembley Stadium, and was subsequently replaced by Federico Bernardeschi in the 86th minute; Italy went on to win the European Championship following a 3–2 victory in a penalty shoot-out after a 1–1 draw in extra-time.

[63] On 6 October, Chiesa assisted Lorenzo Pellegrini's goal in a 2–1 home defeat to Spain in the semi-finals of the 2020–21 UEFA Nations League.

[64] On 10 October, he won a penalty from which Domenico Berardi scored the match–winning goal to give Italy a 2–1 home victory over Belgium in the bronze medal match of the 2021 UEFA Nations League Finals.

[nb 1] His pace and movement off the ball allow him to exploit spaces and make attacking runs to beat the defensive line and provide depth to his team.