“Good to see you,” Halstead says to his ex-wife, Upton, in a brand new teaser for One Chicago’s 2026 crossover.
A three-part One Chicago crossover event is coming as the valiant heroes of Chicago Med, Chicago Fire, and Chicago P.D. join forces to save the day, and it looks like Chihards are being treated to the return of two legendary Chicago P.D. stars: Detectives Jay Halstead (Jesse Lee Soffer) and Hailey Upton (Tracy Spiridakos).
That’s right, Upstead is so back. For years, Chihards relished in the swoon-worthy relationship between Detectives Halstead and Upton, one of the most unforgettable One Chicago love stories and tragedies. Years of will-they-wont-they tension grew into a passionate partnership and relationship. The pair even tied the knot in an intimate courthouse ceremony. However, not long after celebrating their nuptials, Halstead’s desire to start anew caused the couple to drift apart, culminating in a heartbreaking long-distance divorce and very little closure for fans.
Now, Upton and Halstead are set to return in One Chicago’s 2026 crossover event, which sees all hands on deck across Chicago Fire, Chicago P.D., and Chicago Med.
What we learned about Halstead and Upton in the crossover teaser
“We made a vow to protect this city,” Sergeant Hank Voight (Jason Beghe) says in the 15-second crossover teaser, which debuted Wednesday, February 4 following Chicago Med.
In one clip, we see Firehouse 51 icon Kelly Severide (Taylor Kinney) scale the side of a Chicago skyscraper, in another, we see flashes of Gaffney heartthrob Dr. John Frost (Darren Barnet) rushing into the Emergency Department to help a patient. However, the most exciting moment was the appearance of familiar face, Intelligence Unit icon Jay Halstead, who looked pretty nervous, but not due to the city-wide crisis at hand.
“Good to see you,” Halstead said to a blood-splattered Upton, who returned her ex-husband’s greeting with a simple look.
Halstead and Upton’s separation occurred largely off-camera, with no explosive argument or back-and-forth. Halstead left for Bolivia, and Upton originally thought he’d come back, only to have her heart broken with no returned phone calls.
Needless to say, it was a doozy for Upstead fans. While Soffer has returned to direct the occasional P.D. episode since his 2022 exit, the One Chicago crossover event serves as the first time fans will see Jay Halstead back on screen since he left Chicago.
Why did Jay Halstead and Hailey Upton leave the Intelligence Unit?
Upon growing disheartened with the increasing moral ambiguity on the squad, Halstead chose to resign from the Intelligence Unit in Season 10’s “The Great Man” to accept a job with the army to hunt down drug cartels in Bolivia. Upton was heartbroken by her husband’s decision, but after he vowed they’d make it work as soulmates, she supported her husband.
“We all really wanted to do justice for Halstead’s character as best we could — to who he’s been for the show — we really wanted to make that decision to leave his own decision,” showrunner Gwen Sigan said at the time. “For it to come from him. It felt important to keep him alive and keep him out in the world trying to do good. The idea of him getting back to who he was gave us that opportunity.”
Despite his promises of an eventual happily-ever-after, Halstead’s minimal communication with his wife and his failure to book a return home ticket led Upton to make the devastating decision to file for divorce. After much heartbreak and toil over what was best for her, Upton left the Intelligence Unit in the Season 11 finale of Chicago P.D. (“More”) to an unknown job in a new town, moving away from the Windy City to start a new chapter on her own.
“I think I took a lot of comfort in that it was happy,” Spiridakos told us of her character’s final scene. “I loved that on the ride to the airport, she smiles… And so I didn’t really fill in the blank. I just kind of let it be, but I loved that it was in this positive vibe. She’s going into this happiness, which we haven’t gotten to see a lot of with her.”
