2026 One Chicago Crossover: Are Upton And Halstead Back Together?
Contains spoilers for "Chicago Fire" Season 14, Episode 13 — "Reckoning, Part I," "Chicago Med" Season 11, Episode 13 "Reckoning, Part II" and "Chicago P.D." Season 13, Episode 13 — "Reckoning, Part III"
It's been months since they've seen each other, but Hailey Upton (Tracy Spiridakos) and Jay Halstead (Jesse Lee Soffer) pick things up right where they left off as guest stars in the latest One Chicago franchise crossover event. Is their romance still alive? The answer is a big "maybe" — it's clear that the exes have some unresolved feelings, and they end the episode vowing to share a drink together.
Hailey is now working as a Special Agent with the FBI in Detroit, and when she figures out Jay's Bolivian mission is about to blow up, she involves herself in the case. Jay then saves Hailey from an assailant, and they team up to figure out why and how Jay's drug mule target managed to release a toxin onto a plane — killing over a hundred people as well as himself. But when the dust settles and the incident's put to bed, Jay admits to Hailey that he wishes he had reached out to her before, and he's sorry for how he handled their break-up. Hailey is willing to listen, and they agree to meet and talk more instead of flying back to their respective responsibilities.
Does that mean romance is in the air? Spiridakos doesn't think so — yet. "For Hailey, I think it was a conversation that opened the door to further conversations for her," she told NBC Insider. "She was quite hurt by how things were left off, but there is such a big history, even outside of the romantic relationship that they were in."
Hailey and Jay were in a rough place when they saw each other last
It's no wonder that Hailey is so reluctant to forgive Jay. After the pair become close while serving as partners in the field, they marry during Season 9 of the police procedural. But during Season 10, Jay realizes he's unable to cope with the moral nuances of police work and quits the force.
He takes up his aforementioned Bolivian mission without telling Hailey or anyone else on the team, and divorces her long-distance. All in all, it's a bizarre exit that made "Chicago P.D." fans livid. Hailey struggles in the wake of his abandonment, and both Upton and Tracy Spiridakos ultimately exited the show during Season 11.
But that's all water under the bridge now. Even though they aren't officially reunited as a couple yet, at least one person thinks there's blue skies ahead for the star-crossed duo. "I think there's definitely hope there," "Chicago P.D." showrunner Gwen Sigan told TV Insider. "I think they're different than they were years ago. I think they're in a better spot, each of them in their own lives. And I think they have new perspective on everything that happened between them all those years ago. So, yes, I think there's hope." While Spiridakos and Jesse Lee Soffer aren't returning to the procedural any time soon, at least those who love Upstead finally have a reason to smile.