Tracy Spiridakos (who starred as Hailey Upton) left Chicago PD in season 11. Consequently, Halstead and Upton's relationship was doomed.

Jesse Lee Soffer is set to star as Wes Mitchell in FBI: International season 4, which is the actor's first TV role after leaving Chicago PD​​​​​.

Upton replaced Sophia Bush's Erin Lindsay when she exited Chicago PD after season 4. Not only did Upton take Lindsay's spot in the Intelligence Unit, but she also stepped in as Halstead's love interest. Over time, Halstead and Upton developed feelings for one another. In season 8, the two characters finally gave in to their feelings and were married by the middle of season 9. However, their marriage evidently was built to last as Halstead quit and reed the military in Chicago PD season 10, episode 3, leaving Upton behind in Chicago.

Chicago PD Season 11 Failed To Fix Halstead & Upton's Relationship

Halstead & Upton Got A Divorce

Even though Halstead and Upton tried to make their relationship work after he quit the Intelligence Unit and moved out of the country, it couldn't withstand the long distance in Chicago PD seasons 10 and 11. Halstead started pulling away from Upton. He wasn't answering her calls, and he extended his deployment without telling his wife. So, it was only a matter of time before Halstead and Upton officially ended their marriage in Chicago PD​​​​​​.

Seeing [Jesse Lee] Soffer and [Tracy] Spiridakos in an apparent relationship is likely exciting for some Chicago PD fans, but it's also a reminder of what could have been for Halstead and Upton.

There was no way for Halstead and Upton to fix their relationship as they were apart for so long. So, Upton finally filed for divorce and signed the papers during the Chicago PD season 11 premiere. Despite their breakup, Tracy Spiridakos' exit opened up the door for Halstead and Upton to rekindle their relationship. Unfortunately, that didn't happen, and Upton quit the Intelligence Unit and left Chicago at the end of the Chicago PD season 11 finale without disclosing where she was going or what she was going to do next.

Jesse Lee Soffer & Tracy Spiridakos Confirm That They Are Dating

The 2 Chicago PD Stars Went On A European Trip Together

In late August 2024, Jesse Lee Soffer and Tracy Spiridakos posted on their individual Instagrams with pictures of them vacationing in Europe, sparking romance rumors between the two actors. Seeing Soffer and Spiridakos in an apparent relationship is likely exciting for some Chicago PD fans, but it's also a reminder of what could have been for Halstead and Upton. With the two characters out of the Intelligence Unit and Chicago, it would make sense for them to reunite. Alas, fans will have to settle for a real-life romance between Soffer and Spiridakos instead of Halstead and Upton in Chicago PD.

Source: Instagram