Former detective Hailey Upton as portrayed by Canadian actress Tracy Spiridakos, is a former member of the Chicago PD Intelligence Unit who officially exited the series in the Season 11 finale, "More," on May 22, 2024.

Following the traumatic kidnapping of her mentor, Sergeant Hank Voight, and her own struggle with her divorce from Jay Halstead, Upton decided she needed a "fresh start". She resigned from the CPD and was last seen in a taxi heading to the airport, smiling with a sense of hope.

Hailey grew up in Chicago's Greektown neighborhood, where her parents owned a diner. A traumatic childhood incident, where her father being assaulted during a robbery, where he was seriously beaten, and this incident profoundly impacted her.

Upton experienced domestic abuse in her household, where her father was abusive, both physically and emotionally. With this background, she was shaped, therefore, fueling a strong personal drive for her to protect the vulnerable and stand against abusers.

Likely in part to her own rough upbringing we see Hailey, during her later seasons on Chicago PD following down the path of blurred lines and questionable conduct employing similar 'ends justifying the means' type behaviors exhibited by her Sergeant Hank Voight.

This scenario takes place after her departure from the Chicago PD. It's late May 2024 and Hailey has found herself in Detroit as she considers her next step in life.