“Upstead” boasts a long and storied One Chicago history as one of P.D.’s most iconic couples.
There have been countless slow-burn romances over the years on One Chicago, but few are as unforgettable as the bittersweet love story between Chicago P.D. fan favorites Jay Halstead (Jesse Lee Soffer) and Hailey Upton (Tracy Spiridakos).
Partners for several years as Intelligence Unit icons before sparks began flying, it didn’t take long for Chihards to root for an “Upstead” happily-ever-after. P.D. fans watched the couple fall in love, share their first kiss, swap vows in a secret elopement, and even begin to take the next steps together as newlyweds. After a heartbreaking twist of fate for the P.D. power couple, both Halstead and Upton left the Windy City, but they are set to return in P.D.’s Season 13 crossover event. Needless to say, Upstead fans won’t want to miss it.
But that doesn’t mean that fans didn’t see the writing on the wall. Below, we take a look back at Halstead and Upton’s relationship history on the show.
Upton and Halstead first met in Season 4 of Chicago P.D.
Upton was first introduced to both Halstead and the rest of the Intelligence Unit in Episode 21 (“Fagin”). At the time, she was a detective in Robbery-Homicide and collaborated with Intelligence on a winding case.
Upton and Halstead were great partners from Season 5-7
After Upton was assigned as Halstead’s partner in Intelligence, the two became increasingly close—but without making their relationship romantic. From Upton encouraging Halstead to go to therapy for PTSD to her opening up about her childhood abuse—and even kidnappings, suspected murder, and multiple near-death experiences—their bond slowly grew beyond their police work. Even when Upton dated Ruzek in Season 6, it did little to break her friendship with Halstead.
By the end of Season 7, it was clear Upton and Halstead had the potential to take things to a romantic level—especially during “Mercy” when Upton doesn’t leave Halstead’s side in the hospital after he’s shot. In response to a colleague’s remark that she loved Halstead, Upton replied, “Of course I love him, he’s my partner,” revealing her true feelings.
Later on in Season 7’s “Silence of the Night,” fans saw both cops openly admit that they missed one another after Upton was tasked with going to New York to work with the FBI.
Upton and Halstead shared their first kiss in Season 8 of P.D.
Finally, after several seasons of simmering tension, Halstead and Upton had their first kiss in Season 8, Episode (“Tender Age”). The moment marked the official beginning of “Upstead,” as their romance continued to grow. They said “I love you” to one another in Episode 11, and Voight found out about their relationship in Episode 14, bringing the partners even closer.
By the Season 8 finale, shaken by her accidental murder of the suspect in Kim Burgess’ kidnapping (which Voight covered up), Upton proposed to Halstead, telling him that she never wanted to lose him.
Upton and Halstead got married in P.D. Season 9
By the end of the Season 9 premiere, Halstead accepted Upton’s surprise proposal, better yet returning the favor by asking her to marry him, confessing that he knew for years that they were meant to be. They moved in together, with the rest of the Intelligence Unit soon finding out about their relationship, as the two were intent on keeping their partnership strictly professional while on the job.
Later on in the season, amidst the mess caused by the events of the Season 8 finale, Halstead no longer wanted to waste any time and insisted that he and Upton get married ASAP. The couple did just that, eloping with a secret courthouse wedding in the season’s fall finale.
“It really was the perfect way for that to happen. It really stays really true to those two characters,” Spiridakos told TV Insider. “It wasn’t a big celebration because it’s just for the two of them. Things have been so fractured for so long between them that it was a moment for the two of them to reconnect and kind of show that they’re in this together and they’re going to move forward together.”
Jay Halstead left the Windy City (and Upton) in Season 10
Unfortunately, Upstead fans everywhere were let down when Soffer’s Season 10 exit from the show meant that we’d no longer see the newlyweds on our screens. After becoming unhappy with the increasing gray areas in his policing, Halstead resigned from the Intelligence Unit and left Chicago— also leaving Upton. The detective took a job with the army to hunt down drug cartels in Bolivia.
“It’s black and white, it’s good and bad, it’s right and wrong, and it’s no more of this,” he told Upton about his new job. “I need that. I need that back. I fly out today. It’s not forever, it’s eight months, maybe a little longer. But I swear to you that we’re gonna get through this because you’re the love of my life, and if I’m yours, then you’ll know that you have to let me go.”
Despite springing that he was moving thousands of miles away with basically no notice, his words left the tiniest bit of hope for fans. But this heartbreak would be tough for Upton to get over.
Halstead ghosted Upton in Chicago P.D. Season 10
During Season 10, Episode 12’s “I Can Let You Go,” Upton called Halstead’s boss after weeks of being unable to contact him. After learning Halstead had extended his tour in Bolivia without telling her, she broke down in tears.
“It’s the first time we see her break down since he’s left, since their goodbye,” Spiridakos told Variety at the time. “I think there’s gonna be some changes for her over the next little while.”
The actress continued, “She still considers herself still married,” she says. “I think her taking [her ring] off, I’m sure there will be a moment that will come. I assume that’s coming. I’m interested to see what that will be like. Is that a goodbye? Is that self preservation?… I’d like to explore is what that feels like to have been in such a raw place and she’s not overly open anyway. I feel that she probably will just shut that door for a long time.”
Despite their recent nuptials and Upton’s support for Halstead’s relocation, his failure to keep Upton updated about ever returning to the Windy City drove a major wedge in their relationship. After finding herself in a life-or-death scenario and realizing Halstead wouldn’t have had no idea, Upton started to contemplate whether or not she should remain married.
“You know it is OK to let go if you’re the only one fighting. Doesn’t mean you don’t love ’em, just means you love you, too,” Voight told Upton.
Upton filed for a divorce — and left the squad in Chicago P.D. Season 11
After heeding Voight’s advice and six months of soul searching, fans were nonetheless heartbroken during the Season 11 premiere of Chicago P.D. when Upton signed divorce papers. After years of will-they-won’t-they and on-again-off-again romance, Upstead was officially over. As show runner Gwen Sigan confirmed to NBC Insider, conversations happened off-camera between the couple that ultimately led to their split.
“It’s nice that it happened offscreen and that now things are in a place of closure as far as pragmatically speaking, but not as far as emotionally speaking,” Sigan explained. “Yeah, and just getting to see now that we’ve gotten there, we can actually concentrate on what’s next for her, you know? What’s next, and what is the light outside of it? Because that relationship wasn’t all bad, but it’s just that pain has been the dominant thing that we got to see last season, so now what is it? What is it gonna look like?”
After choosing to prioritize her own needs outside of the Intelligence Unit, Upton ultimately decided to turn in her badge during P.D.’s Season 11 finale. After looking through different job openings, Upton booked a plane ticket and got out of dodge, eager to start a new chapter after the Intelligence Unit.
Upstead reunite in Chicago P.D. Season 13
Despite their ill-fated end, Chihards adored the story between Upton and Halstead, which will continue during the 2026 One Chicago crossover event between P.D., Chicago Fire, and Chicago Med. Upton is back in the Windy and working with the FBI on a nail-biting case, while Halstead has returned on an undercover assignment that brings them back together again. How will this Upstead reunion shake out? Chihards can’t wait to see.
Don’t miss Upton and Halstead’s triumphant return by tuning in for the three-hour One Chicago crossover on Wednesday, March 4, beginning at 8/7c on NBC. Unlike typical One Chicago Wednesdays, Chicago Fire will lead the cavalry of One Chicago crossover episodes at 8/7c, followed by Chicago Med at 9/8c, and Chicago P.D. at 10/9c.
