Chicago PDhas had many romances over the course of its 11 seasons, with one of the favorites being between Jay Halstead and Hailey Upton despite their lack of a happy ending (but that may not be the case in real life). The NBC police procedural TV series follows the law enforcement officers of the Intelligence Unit in Chicago, which used to include Halstead and Upton. Sadly, Jesse Lee Soffer (who played Halstead) exited the show during season 10, andTracy Spiridakos (who starred as Hailey Upton) leftChicago PDin season 11. Consequently,Halstead and Upton’s relationship was doomed.
Jesse Lee Soffer is set to star as Wes Mitchell inFBI: Internationalseason 4, which is the actor’s first TV role after leavingChicago PD.

Upton replacedSophia Bush’s Erin Lindsay when she exitedChicago PDafter 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 rejoined the military inChicago PDseason 10,episode 3, leaving Upton behind in Chicago.
Even though Halstead and Upton tried to make their relationship work after he quit the Intelligence Unit and moved out of the country, itcouldn’t withstand the long distance inChicago PDseasons 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 beforeHalstead and Upton officially ended their marriage inChicago PD.

Seeing [Jesse Lee] Soffer and [Tracy] Spiridakos in an apparent relationship is likely exciting for someChicago PDfans, 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 theChicago PDseason 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 oftheChicago PDseason 11 finalewithout disclosing where she was going or what she was going to do next.

FBI: International Makes Up For Chicago PD’s Biggest Jesse Lee Soffer Missed Opportunity
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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 SofferandTracy Spiridakosposted 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 someChicago PDfans, 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 Spiridakosinstead of Halstead and Upton inChicago PD.
Chicago P.D.
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Chicago P.D.: This police drama, set in Chicago’s District 21, follows the distinct units within the Chicago Police Department—uniformed officers addressing street crimes and an Intelligence Unit tackling major offenses such as organized crime and drug trafficking, capturing the dedication of those who serve and protect their community.