Did we just see that right? Are we getting a shocking reunion?
For a while, we’ve known that the One Chicago franchise would be staging another massive crossover event.
Getting two of them within the span of two seasons feels like quite the treat, considering the franchise had abandoned large-scale crossovers well ahead of the pandemic.
But the 2025 Chicago Crossover event was so wildly successful that it’s no surprise the network would decide to go big once again.
It’s also a great reward for viewers who will have to wait patiently for the series to return, since it’s going on hiatus for the Winter Olympics.
Unfortunately, that means we won’t be tuning in to see our favorite characters across Chicago Med, Fire, and PD until March 4.
But after that brief teaser they shared with us, it’s certainly going to be worth the wait when the series returns.
Once again, we can already tell that this crossover may lean heavily into Chicago PD. If you tracked the last event, many felt that the mass attack leaned more heavily into PD and Chicago Fire than it did Med.
And this time, given that it is supposed to bring back two of the franchise’s most beloved characters, both from PD, that may be the case here.
The last crossover felt like the Avengers Assembling, something Med’s Steven Weber shared with us when promoting it.
And he certainly was onto something with a well-blended event that had everyone from all corners of the franchise joining forces in an adrenaline-inducing event that genuinely felt like a blockbuster movie event.
But the 2026 Crossover Event could really double down on that Avengers Assembling energy by actually bringing back characters we haven’t seen in years.
Not only does the excitement and curiosity lie in Hailey Upton and Jay Halstead’s returns, but it’s in actually seeing the two reunite onscreen for the first time since their divorce.
One of the most shocking moments in Chicago PD Season 10 came when a dark case pushed Jay Halstead to his limits, leading him to recognize that working for Voight brought out the worst in him.
It resulted in him leaving the unit, but also his wife, Hailey, during Chicago PD Season 10 Episode 3.
He was reeling and trying to piece himself together again, flailing in trying to figure out if he was still a good man.
Halstead took an opportunity in the army, which sounds like a joint task force situation with the army and the DEA that had him going undercover in Bolivia and busting up drug cartels.
When he left Upton and the others, it seemed like there would be a chance that he’d still be in communication with them, but as we tuned into the remainder of that season and all of Chicago PD Season 11, it was pretty clear that Halstead abandoned Upton.
He didn’t respond to her letters or calls, had a go-between who relayed certain things, and eventually, Upton took the hint and sent him divorce papers, which he signed.
It was a crushing end to a fan-favorite couple, certainly controversial. But it was also a very rough ending for Jay Halstead and tarnished his image significantly after his departure.
It’s possible this crossover event could be a pathway toward fixing what PD’s writing broke: the end of his story ultimately had him fleeing Chicago, abandoning his wife, and going off the grid, never communicating with anyone else again.
Many viewers may just be content with having Halstead return at all, and they’ll certainly be happy to have Jesse Lee Soffer back onscreen again.
Sadly, his venture on FBI: International ended during one of CBS’s most polarizing cancellations last May.
But what can they sell us during a three-hour crossover event that changes the impression they left us with after Halstead’s hasty departure?
Meanwhile, Hailey stuck around for another season before she, too, left the unit after months of a downward spiral and a near loss of Voight, whom she had developed an unusual, family-tinted, codependent relationship with.
Hailey departed the series during Chicago PD Season 11 Episode 13, realizing that she needed a change of pace and a fresh start.
Back then, we didn’t know which federal job she would take, but she got in a cab and departed the Windy City, presumably for good.
Now, we know that she took up a job with the FBI. She’s been working on a joint task force with the drug enforcement team in Detroit, but now the crossover’s big event will pull her back to Chicago.
Firehouse 51 is called to an airfield when a passenger jet suddenly goes silent mid-air, triggering a high-stakes emergency. Their discovery cracks open a bigger and deadlier mystery — one with consequences that could ripple far beyond the runway and put countless lives in jeopardy.
As best as we know, neither has kept in touch with the other since Halstead left the country, so bringing them together again with all that tension, betrayal, and hurt, even years later, is where the real action and explosiveness come into play.
One Chicago will have a lot of work to make this reunion worthwhile.
It’s something to approach with trepidation, and perhaps the diehard Upstead shippers will be just excited to get a glimpse of their favorite characters, especially onscreen together, but for the rest of us, we’re going to need more answers.
Can One Chicago even walk back the way they decimated their relationship? And would we even want them to? Or is it something that could feel like fan service and nothing else?
It’ll also be interesting to see how each of these characters interacts with other members of the team. Jay, in particular, left everyone behind without saying goodbye to anyone outside Voight.
Hailey wasn’t the closest to others by the end, but it’ll certainly be interesting to see how she fares around a newcomer like Imani.
The case seems like something that will have them deep in the throes of action, so we’ll probably have to see Upstead work together for well over two hours before they ever even get to properly talk.
But if the teaser showing Jay casually saying “Good to see you” to a bloody Upton, who seems at a loss for words, is any indication of how their first interaction in three years will go, color me intrigued.
