Chandler O'Leary is an accomplished illustrator and lettering artist based in Tacoma, Washington. She graduated from the Rhode Island School of Design (RISD) and founded her own stationery imprint, Anagram Press, in 2004. Living and working in the Pacific Northwest, she resides in a century-old Craftsman house overlooking the Salish Sea with her husband and son.

Chandler is known for her illustrated travel blog, Drawn the Road Again, and has published several books, including The Best Coast: A Road Trip Atlas in 2019 and a companion book of postcards in 2020. Her most recent work, On Island Time: A Traveler's Atlas, was published in March 2023. In 2016, she co-published Dead Feminists, which won a Pacific Northwest Book Award, and she continues to collaborate on the ongoing Dead Feminists broadside series with Jessica Spring.

Her work often connects quotes from historical women with contemporary political and social issues. In addition to her client work, Chandler spends time on personal side projects and posts her sketches and art on her blog. She has received numerous awards and recognition for her contributions to the arts, including the Wright Artist Fellow Award and the Tacoma Artists Initiative Program Award.