Dlott was born in Dayton, Ohio, on September 11, 1949, to Jewish Russian immigrant parents.

[3] In 1981, Dlott became the first female partner at Graydon Head & Ritchey, a Cincinnati law firm.

[5][6] In 2004, Chesley purchased "what is believed to be the most expensive single-family home listed in Greater Cincinnati, possibly ever," a six-bedroom, seven-bathroom, French chateau-style home on 5.3 acres (21,000 m2) nestled into 300 acres (1.2 km2) of private green space with 27,000 square feet (2,500 m2) of living space.

[7] Dlott and her husband were victims of a violent, armed home invasion robbery by "three black men with guns and masks", Terry Darnell Jackson, 21, Demetrius Williams, 20, and Darrell Joseph Kinney, 20,[8] on December 4, 2015.

[9] The three perpetrators were apprehended and pleaded guilty, and in April 2016, the men were all sentenced to 34 years in prison.