At the 2013 P&G National Championships, Chiles finished eleventh in the all-around with a score of 108.050. She finished sixth on vault She was selected to be a member of the Junior National Team.
2014
Chiles made her international debut at the 2014 City of Jesolo Trophy. She won a gold medal with the team and finished sixth in the all-around. In the event finals, Chiles placed second on vault behind her teammate Bailie Key. At the 2014 Secret U.S. Classic, Chiles won the all-around competition with a score of 57.350.
2015
After a tough competition, Chiles placed eighth in the all-around at the 2015 U.S. Classic. She won vault at the national championships and was selected for the national team.
In August, 2017 Chiles competed at the 2017 U.S. National Gymnastics Championships where she placed second in the all-around behind Ragan Smith, in addition to a fourth place finish on beam. During her balance beam performance she flubbed a wolf turn but saved it by connecting it to an unplanned triple turn. In September, Chiles was selected as the non-traveling alternate for the 2017 Artistic Gymnastics World Championships.
2018
On March 18, Chiles made her senior international debut at the Stuttgart World Cup where she placed third behind Jin Zhang of China and Elisabeth Seitz of Germany, posting the highest scores of the competition on vault and floor. On April 8, Chiles was named to the team to compete at the 2018 Pacific Rim Gymnastics Championships. There she won team gold as well as gold on vault and floor exercise and bronze on balance beam. In August Chiles competed at the National Championships where she placed 11th in the all-around and second on vault behind Simone Biles. She also placed 10th on uneven bars, 14th on balance beam, and 21st on floor exercise. She was not named to the national team. She did receive positive recognition for competing in a Wonder Woman inspired leotard. In October Chiles participated in the Worlds Team Selection Camp. During the competition she placed third on vault behind Biles and Shilese Jones, seventh in the all-around and on balance beam and sixth on uneven bars and floor exercise. While she did not make the world team, she posted on Instagram that she was named to the 2018-2019 national team. In November Chiles signed her National Letter of Intent with UCLA, deferring until after the 2020 Olympics and starting in the 2020–2021 school year.
2019
In June it was revealed that Chiles had switched gyms, leaving Naydenov Gymnastics in her hometown of Vancouver, Washington and moving to Spring, Texas to train at World Champions Centre, the same gym Simone Biles trains at. Chiles was expected to compete at the 2019 American Classic. However, days before the competition, she withdrew. At the 2019 GK US Classic in July, Chiles finished eleventh in the all-around with a score of 54.650. She also tied for eighth on bars with Leanne Wong, placed twelfth on beam, and tied for sixteenth on floor with Sloane Blakely. At the 2019 U.S. National Championships in August Chiles performed all eight of her routines without a fall to place sixth in the all-around. She also finished seventh on uneven bars, tied with Riley McCusker, placed twelfth on balance beam, and seventh on floor exercise. As a result she was named to the national team. In September Chiles competed at the World team selection camp and placed eleventh with a score of 53.400 after falling on her Amanar vault and on floor exercise. Despite being named to the nominative worlds team, she did not make the official roster.
