The thing with Upstead is that we always had the hope, if not the certainty, that we could see them back on Chicago P.D. sooner rather than later. Both Jay Halstead and Hailey Upton left the show in very open-ended ways, after all. But not just open-ended for their own individual character arcs, but open-ended for the relationship the show and the fans invested so much time in. So, it made sense that if, at some point, the show could return to them to give the story proper closure, they would.
Despite that, it was still a shock to see both of them in the trailer for the upcoming One Chicago crossover.
We saw Hailey Upton and Jay Halstead’s love story blossom on-screen. We saw them become partners, then friends. We saw them fall in love. Saw them get married. And then, we watched Jay leave. We say Hailey stay and endure, until she couldn’t anymore. Until the silence became too heavy to bear. Then, we saw her give up. We saw her move forward. We said goodbye to hear as she was walking into a new future.
And yet we never lost hope. Open endings are just that, open. And it always felt like Upstead would find their way back to each other, whether we saw it or not. They, after all, broke up over absolutely nothing. So we could imagine them getting back together easily.

Now, hopefully, we won’t have to imagine.
Because that’s the thing, Hailey Upton and Jay Halstead are coming back to us for this next One Chicago crossover. But that doesn’t guarantee a happy ending. Chicago Fire just brought back Carver after writing him out, and we didn’t get a happy ending or closure. In fact, all we got are more answers. So there’s no guarantee here.
There should be, though. There’s no reason to bring both Jay and Hailey back other than to finally give fans the thing they wanted to in the first place, an Upstead HEA. We’d love to keep them after, but since that’s unlikely, at least we’ll be happy to know they’re out there, living their lives together.
And One Chicago has not one, but three episodes to fix it. Enough to have the conversations needed. Enough to repair what they broke. It’s great to see both characters back, don’t get me wrong. But if they are coming back, both of them, they need to leave hand in hand and ready to try together.
For this to be the end of their story, and a satisfying one at that, we need a happy ending. Ball’s on your court, One Chicago. We’ll be watching and waiting.
Are you excited for the One Chicago crossover? What do you want to see from Upstead? Share with us in the comments below! And if you have your own opinion on the show, leave a review/rating on our Chicago P.D. hub!
Chicago P.D. airs on Wednesdays at 10/9c on NBC.
I am really excited to see them back, but I have ZERO confidence in Gwen Sigan to do right by these two characters. She completely destroyed Jay’s character when Jesse decided to leave with a horrible, out of character departure that never made sense. And then she put Hailey through the wringer when Tracy decided to leave. I’ll tune back in for the cross over, but I probably won’t pick the shows up again.