'One Chicago' teases future of fan-favourites Halstead and Upton and we can't wait for what happens next
The 2026 edition of the 'One Chicago' crossover event will be remembered for several things, most notably the reunion of two fan-favourite characters, Jay Halstead and Hailey Upton. The three-part episode, titled 'Reckoning', featured a superior narrative as compared to the 2025 crossover and managed to bring together the best elements from 'Chicago P.D.,' 'Chicago Fire', and 'Chicago Med'. This was also the first instance since the exit of Halstead and Upton from the franchise that the two characters were brought together by the show. Nevertheless, the future of Halstead and Upton in the 'One Chicago'-verse remains unclear.
On 'Reckoning', a mysterious plane accident tragically led to the loss of numerous lives and was initially considered to be an act of terrorism. However, upon further investigation, the mystery turned out to be tied to a past incident in the Windy City 25 years ago involving Dom Pascal, Hank Voight, and Sharon Goodwin. Played by Jesse Lee Soffer, Halstead was a familiar character on 'One Chicago' during the early days of the show. By the time Tracy Spiridakos' Upton joined Voight's Intelligence Unit, Halstead was a core member of the team. The latter's exit from the show was abruptly announced during Season 10.
Halstead and Upton had, by then, tied the knot in a secret ceremony after dating each other briefly. Although Halstead promised Upton he would return for her, he ultimately ghosted her. Naturally, this caused Upton considerable grief, and their marriage concluded with a messy divorce. 'Reckoning' instantly established that, despite living in separation all these years, it was quite evident that both Halstead and Upton still harbored feelings for each other. They were seen running all over Chicago, gathering evidence and chasing down leads, just like the old days. Upton maintained a distance from Halstead throughout, though the duo did have a heartfelt conversation at the end.
Halstead apologized for his past conduct, explaining that he had overwhelmed himself with his job at Intelligence and couldn't reach out to Upton, despite wanting to. Halstead further clarified that he had continued living in Chicago in the hope of running into Upton. The feeling seemed to be reciprocated by Upton. Towards the end of their scene, Upton gracefully offered to buy Halstead a drink, suggesting that she hadn't entirely closed the door on reconciling with her former partner. In hindsight, Halstead's accountability is a step in the right direction, even though it is quite late in the game for him to own up to his actions. It remains uncertain whether the two shall ever be seen together on 'One Chicago' in the days to come.
