Chestnut signed with the Tennessee Titans as an undrafted free agent in 2022.[2] Following the final roster cuts made by the Titans, Chestnut, along with fellow undrafted rookie Tre Avery, made the team. After being inactive the first three games, he was waived on October 1, 2022.[3] He was re-signed to the practice squad on October 4.[4] He was promoted to the active roster on December 17, 2022.[5] He appeared in six games during the 2022 season, making ten kick returns, three rushes, and three receptions for 238 total yards.[6]
Chestnut entered the 2023 season third on the Titans running back depth chart. He suffered a hamstring injury in Week 3 and was placed on injured reserve.[7] He only briefly appeared in three games during the 2023 season.[8]
On March 13, 2024, Chestnut re-signed with the Titans on a one-year contract, once again as the third running back on the depth chart.[9] He made appearances in all 17 games during the 2024 season, recording 102 rushing yards, 11 receiving yards, and 337 kick return yards.[10]
On March 19, 2025, Chestnut re-signed with the Titans on a one-year contract.[11]