Are Halstead & Upton Back Together After The 2026 One Chicago Corssover? Jay & Hailey’s Future Explained

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Be warned, the following contains spoilers for the 2026 One Chicago crossover event! Jesse Lee Soffer and Tracy Spiridakos reprised their roles, bringing Jay Halstead and Hailey Upton back together, but their long-term future as a couple is still uncertain. NBC kicked off the second half of the 2025-2026 season with this special crossover, which featured characters from Chicago Fire, Chicago P.D., and Chicago Med.

Chicago’s emergency services responded to a devastating plane crash with numerous fatalities. Initially believed to be a terrorist attack, the investigation revealed a connection to events that occurred in the city 25 years prior, involving the histories of Hank Voight, Dom Pascal, and Sharon Goodwin.

The 2026 One Chicago crossover event was a clear step up from the previous year’s. The three-episode “Reckoning” storyline was better planned and more engaging, providing a satisfying conclusion for the NBC/Wolf Entertainment shows. A major draw for viewers was seeing Upton and Halstead together again after their difficult split. While their future is still unclear at the end of the event, the story leaves some clues about what might happen next.

Halstead & Upton’s Complicated History Explained

Jesse Soffer was one of the first actors to join the ‘One Chicago’ shows and played a key part in its beginnings. By the time Jay Halstead (played by Spiridakos) joined Voight’s team, Soffer was already a familiar face to viewers. When Soffer decided to leave after the show’s tenth season, the writers had to create a storyline to explain his character’s departure. This happened right after Halstead and Upton had secretly gotten married following a long-term relationship, adding to the complexity.

Halstead’s departure from Chicago PD in season 10 was upsetting because his actions weren’t like him. He’d told Upton he’d return to her, but instead of being honest, he led her on and then abruptly cut off contact. This caused Upton a lot of pain, and ultimately led her to leave and seek a new beginning.

The 2026 One Chicago crossover brought Upton and Halstead face to face for the first time since he left the team. It was clear they still had feelings for each other, but Upton kept her distance. They spent the day working with their old team, investigating cases just like they used to. However, after everything that had happened between them, their final conversation was brief and didn’t allow for a real resolution.

Halstead took responsibility for his actions, explaining he became consumed by his work and repeatedly wanted to connect with Upton. He confessed he stayed on the case in Chicago because of her, and it seemed she felt the same way. Ultimately, Upton suggested they grab a drink, signaling she’s willing to try and rebuild their relationship.

Halstead Takes Accountability For What He Did To Upton, But Will It Work?

It wasn’t realistic to think the 2026 One Chicago event could fully resolve the issues between Upton and Halstead. While it was great to see them return, the special had a lot of ground to cover with so many characters and a main case to investigate. Still, it was satisfying to see Halstead finally realize his mistake and at least apologize to his ex-wife, especially after Upton went through so much because of her actions.

I’m not sure if his heartfelt apology will be enough for Upton to forgive him and give their relationship another try. The recent crossover event definitely showed there are still feelings between them, but that doesn’t mean she’s ready to trust him again. She was incredibly kind to Halstead after she finally let her guard down, and even at the very end, she genuinely wished him well. It’s just what you’d expect from someone who once loved him so much.

Let me tell you, Halstead is skating on thin ice with Upton. Honestly, she has every right to be furious after he put her through so much emotional turmoil, all because he couldn’t get his own head straight. For a while there, it looked like he was even going to try and blame Voight for the fallout between him and Upton. But what Halstead didn’t realize is that after he left, Upton and Voight actually leaned on each other and became stronger as a result. That conversation they had at the end of the special felt crucial, finally starting to get Halstead to see things a little differently.

Halstead needs to do a lot more than just say sorry if he wants to get back together with Upton. He broke promises during their last relationship, so it’s understandable she’s hesitant to trust him again. However, he seemed genuinely willing to make a real effort – when asked about his flight out of Chicago, he said it didn’t matter, suggesting he’d prioritize being with Upton over everything else.

What Are The Chances Of Halstead & Upton Returning To One Chicago Again?

As of now, there are no plans for Jesse Spencer (Soffer) or Marina Squerciati (Spiridakos) to return for season 13 of Chicago PD. Spencer recently finished his role on the CBS show FBI: International, and Squerciati is preparing to star in her own series, Anna Pigeon, on USA Network. Fortunately, both actors remain friendly with their former Chicago colleagues, which means it would be easy to ask them to reprise their roles if the story calls for it.

It was disappointing the 2026 One Chicago event didn’t show more of Upton and Halstead together after the case ended. It would have been great to see them casually enjoying drinks, as Upton invited Halstead to do. Still, ending their story on a hopeful note was much better than the unresolved ending when both actors left Chicago PD. Given the show’s direction and the actors’ departures, it’s unlikely they’ll ever be shown getting back together.

Honestly, if this ends up being the last time we see Spiridakos and Soffer on the One Chicago shows, it feels like a really fitting goodbye, especially for Soffer. But if NBC and Wolf Entertainment ever decided to bring them back, I don’t think anyone would complain – I know I certainly wouldn’t! We’d all be thrilled to see them again.

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2026-03-05 07:09