Madrigal played college baseball for the Oregon State Beavers and was selected by the White Sox in the first round of the 2018 MLB draft.

[4] He did not sign with the Indians and attended Oregon State University where he played college baseball for the Beavers.

[9] Madrigal was selected fourth overall by the Chicago White Sox in the 2018 Major League Baseball draft.

[10] He signed for $6,411,400,[11] and was assigned to the rookie–level Arizona League White Sox before being promoted to the Single–A Kannapolis Intimidators in July[12] and the High–A Winston-Salem Dash in August.

[13] He returned to Winston-Salem to begin 2019 and was promoted to the Double-A Birmingham Barons in June after slashing .272/.346/.377 with 52 hits, 20 runs scored, and 17 stolen bases in 49 games with the team.

[19] On April 24, 2021, Madrigal got his first walk–off hit in his major league career in the bottom of the ninth inning against the Texas Rangers off of pitcher John King, leading the White Sox to a 2–1 win.

[22] On June 15, the Chicago White Sox announced on Twitter that Madrigal had undergone surgery to repair the hamstring and would miss the remainder of the 2021 season.

[23] On July 30, 2021, Madrigal was traded along with Codi Heuer to the Chicago Cubs in exchange for Craig Kimbrel.

While playing with the Triple–A Iowa Cubs, he suffered a fracture in his left hand after he was hit by a Trey Wingenter pitch.