He graduated summa cum laude from Towson University in 2004 with a Bachelor of Science in Music.  In 2012 he received his PhD in History from the University of Maryland.  

For his work in New York State history, Dr. Chiles has been awarded the New York State Archives Partnership Trust Hackman Residency, the New York State Library Cunningham Residency, and the 2019 Annual Archives Award for Excellence in Research Using the Holdings of the State Archives.  In 2021, he was named to the editorial board of The Hudson River Valley Review.

Since 2019, Chiles has served as co-editor of New York History.  He became a Research Associate in History with the New York State Museum in 2021.

His articles have appeared in Environmental History, North Dakota History, New York History, and the Journal of the Gilded Age and Progressive Era; his essays have appeared in larger books from SUNY Press and Edinburgh University Press; he regularly reviews books for numerous regional and national scholarly journals; his op-eds have appeared in the Washington Post, the Albany Times Union, Newsday, and the New York Daily News; and he has contributed to educational television programs including American Experience on PBS.  Chiles’s first monograph, The Revolution of ’28: Al Smith, American Progressivism, and the Coming of the New Deal, was published in 2018 by Cornell University Press.