For years, fans of Chicago P.D. have been left heartbroken by the way one of the franchise’s most beloved couples — Jay Halstead and Hailey Upton, known affectionately as “Upstead” — was written out of the series. Now, with both characters set to return in the upcoming One Chicago crossover event, there’s a real chance the iconic police drama could finally make things right — if it follows the emotional storytelling framework that Chicago Med recently demonstrated can deliver meaningful closure.
Upstead’s story became one of the most discussed arcs in Chicago television history. Their slow-burn relationship — from trusted partners to deep romantic love — won over fans over multiple seasons. They eventually married, and viewers invested in their journey expected to see them together for the long haul.
But Halstead’s exit from the series — driven by the actor’s decision to leave the show — was abrupt and left many fans feeling unsatisfied. In Season 10, Halstead accepted a new role with the U.S. Army and departed for Bolivia, leaving Upton behind and effectively putting their relationship on an indefinite pause.
The impact of that departure was felt on-screen as much as off. Upton’s character became deeply affected by his absence, throwing herself into work and struggling with unanswered feelings — and fans globally mourned what felt like an unfinished story.
Matters only deepened when Season 11 of Chicago P.D. revealed that the once-married couple had finalized a divorce, leaving viewers even more frustrated that such a compelling relationship had concluded without closure.
Enter the One Chicago crossover. According to official promotional material and industry reports, both Halstead and Upton are appearing in the upcoming multi-show event airing this March, marking their first significant return to Chicago P.D. since their exits.
That crossover creates a narrative opportunity: one last moment to address their unresolved emotional arc. Fans are hopeful that — much as Chicago Med managed to reunite beloved characters within a single episode earlier this season — Chicago P.D. can repeat that achievement and offer Upstead a satisfying moment of resolution.
In Chicago Med, characters who had drifted apart were brought back together briefly but meaningfully, demonstrating that satisfying emotional closure can be achieved even within the tight time-frame of a standalone episode. Viewers praised that story for giving depth, hope, and warmth to characters fans care about — and Chicago P.D. now has the chance to do something similar for Halstead and Upton.
Of course, some fans are cautious. Simply bringing the pair back together in a crossover doesn’t guarantee a happy ending, and the characters’ complex current positions — with Upton now working for a federal agency and Halstead overseas — create challenges for a traditional reunion. But with three shows tied together and plenty of dramatic potential, this multi-episode event could finally give Upstead the emotional closure viewers have been longing for.
Whether that closure takes the form of a heartfelt reunion, a bittersweet goodbye, or even just a final conversation that honors their history, one thing is clear: Chicago P.D. now has its best chance yet to redeem one of its most heartbreaking endings. Fans will be watching closely to see if the show rises to the moment.