Following his second year in college, Little was chosen by the Chicago Cubs in the initial round of the 2017 MLB draft and was assigned to play for the Eugene Emeralds. However, his performance with the team wasn't stellar, as he ended up with a win-loss record of 0-2 and a high ERA of 9.37 over six starts.
The subsequent year, Little played for the South Bend Cubs during the 2018 season, where he had a record of 5 wins and 11 losses, accompanied by an ERA of 5.15 in 22 games, mostly as a starter. In 2019, he began with the Myrtle Beach Pelicans but had to start on the injured list. Upon his return, he alternated between South Bend and Myrtle Beach, showcasing varying levels of performance with different ERAs.
Due to the COVID-19 pandemic, the minor league season was canceled in 2020, affecting Little's playing schedule. He returned to action in 2021, transitioning into a reliever role and playing for the Tennessee Smokies and Iowa Cubs. Despite the change, he managed a decent ERA of 3.24 across 26 games with a notable number of strikeouts.
Little's breakthrough into the major leagues came on August 30, 2022, when the Cubs promoted him from Triple-A to the MLB roster. He made his debut against the Toronto Blue Jays but was later moved back to Triple-A Iowa on September 1 after being removed from the 40-man roster.
In 2023, Little remained with Triple-A Iowa throughout the season, participating in 50 games and maintaining a 4.05 ERA while recording 73 strikeouts in 73 and one-third innings pitched.
