In the latest One Chicago crossover event, Hailey Upton and Jay Halstead teamed up for a high-stakes case involving a chemical attack. The former couple, who parted ways after Halstead's abrupt departure to Bolivia, shared a tense but professional collaboration. Showrunner Gwen Sigan hinted at potential reconciliation during their emotional exchange.
The One Chicago crossover, which aired on Wednesday, brought together characters from Chicago Fire, Chicago Med, and Chicago P.D. for a three-hour storyline centered on a mysterious chemical attack. The incident began with an airplane full of passengers being wiped out and later posed a threat to Chicago's first responders.
Hailey Upton, played by Tracy Spiridakos, worked as an FBI agent, while Jay Halstead, portrayed by Jesse Lee Soffer, operated undercover. This marked their first encounter since Halstead left Upton mid-marriage and relocated to Bolivia without explanation. Despite the personal history, Upton maintained professionalism and collaborated effectively with her ex-husband on the investigation.
Throughout the crossover, the pair had significant interaction but avoided discussing the past initially. Near the episode's conclusion, they confronted their issues. Halstead admitted, "Hailey, I stayed to work this case because you were here." Upton responded, "I came here because you were here. Good luck, Jay. I wish you the best. I always do."
Halstead then apologized for "all of it," leading Upton to suggest they grab a drink afterward. Chicago P.D. showrunner Gwen Sigan commented on this development in an interview, stating, "They have a lot of conversations to be had still, but we liked the idea of a hopeful sort of opening for the two of them. There's a lot of possibility in that."
Sigan further elaborated that, in her view, the characters proceed to have that drink and continue addressing their past. She expressed hope that their story might continue in future episodes, noting, "Hopefully that just continues and continues, and maybe they come back again. That would be wonderful."
The reunion highlighted lingering affection between Upton and Halstead, suggesting a path toward mending their relationship while resolving the immediate crisis.