Chicago PD boss promises fans there’s ‘definitely hope’ for Upstead getting back together

When it was announced that Jesse Lee Soffer and Tracy Spiridakos would return for the 2026 One Chicago crossover, fans quickly began hoping their appearances could lead to a reunion for their characters. No, we’re not talking about the pair simply reuniting on screen; we’re talking about mending the fences and perhaps finding their way back to one another after their relationship fell apart.

The demise of Upstead is still one of the most painful breakups we’ve had to experience within the One Chicago franchise. Upton and Halstead’s romance was a slow burn over the years, and just when the pair finally tied the knot and seemed to get their happy ending, a series of unfortunate events led to their divorce.

It began when Soffer decided to exit the show. After turning in his gun and badge, Halstead left the CPD and reenlisted in the military, which took him overseas to Bolivia. Through this new role, Halstead began working to dismantle drug cartels and found his center again after needing to step away from the Intelligence Unit, which had corrupted his moral compass with how frequently the unit operated in shades of gray.

He’d eventually extend his leave, and communication with Upton began to fracture beyond repair. The couple separated off-screen, divorcing shortly before Upton decided to leave the Intelligence Unit as well in order to start fresh as she joined the FBI.

In the crossover, we got to see Upton and Halstead back together on screen for the first time since Soffer’s exit. By the end of the episode, Halstead had apologized for putting Upton through what he did and the pair left the CPD building together to get a drink. The moment seemed to hint that perhaps Upstead might get a second chance at happiness, and this is not just wishful thinking.

“I think there’s definitely hope there,” Chicago PD showrunner Gwen Sigan told TV Insider about the couple’s odds of reconnecting following the crossover. “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.”

Giving the fans hope was by design as the creative team saw the returns of the two characters as a chance to give them a brighter sendoff. As Sigan noted, in bringing the characters back and ending the crossover with the pair heading out together to get a drink, the goal was for the moment to “feel very hopeful and positive.”

For now, there are no current plans for the pair to return, but the door is being left wide open. We can only hope that should the characters make their way back to Chicago PD, that drink the couple enjoyed together after saving the day might lead to a fresh start for the pair. There’s no denying that Halstead and Upton both care for one another; this was evident throughout the crossover, and it’s nice to think that the pair might actually get a second chance at happiness together as a couple.

It’s also nice to think that we might be lucky enough to see Soffer and Spiridakos return to Chicago PD someday, even if just for another guest appearance. Hopefully, the next time the pair passes through Chicago, they’ll be back together!