The Windy City’s finest first-responders dealt with a mysterious plane tragedy that killed many in an instant. Eventually, what was touted as an act of terrorism ends up being something related to what happened to the city 25 years ago — which involved Hank Voight, Dom Pascal, and Sharon Goodwin.
Overall, 2026’s version was a significant improvement from the 2025 One Chicago crossover. The three-part “Reckoning” was a more well-executed, compelling, and overall better culmination of the NBC/Wolf Entertainment franchise. Aside from the case and various pairings, one of its biggest appeals is the reunion of Upton and Halstead following an ugly divorce. At the end of the 2026 One Chicago crossover, their fate remains uncertain, but there are hints of what the future holds for them.
Halstead & Upton’s Complicated History Explained
Soffer played an integral role in the earliest years of the One Chicago series as one of its original cast members. By the time Spiridakos was introduced and made part of Voight’s Intelligence, he was already a well-established player in the franchise. During the show’s milestone 10th season, it was announced that he was leaving the show, resulting in the writers having to find a way to explain his exit. To make it trickier, this was immediately after Halstead and Upton got secretly married after dating for a while.
Unfortunately, the majority of his actions leading to his departure were uncharacteristic, making Halstead’s Chicago PD season 10 exit was so disappointing. He did promise Upton, however, that he would come back for her after a period of time. Instead of staying true to his promise, he proceeded to string her along and then eventually ghost her. This resulted to a lot of personal grief for Upton, and eventually, she also decided to leave in search of a fresh start.
When the pair reunited in the 2026 One Chicago crossover, it marked the first time that they came face to face since Halstead’s departure. Upton understandably tries to keep a distance between them, although it’s clear that they both still have feelings for each other. After spending the whole day getting re-acquainted with their old team and running around Chicago chasing leads like the old times, the former couple had one last conversation, albeit far from a proper extensive one, considering everything that happened between them in the last several years.
Halstead tried to take accountability for everything he did, explaining that he lost himself in the job with Intelligence and that he wanted to reach out to her so many times. He also admitted that he stayed in Chicago to work the case because she’s there. Apparently, the feeling was mutual. In the end, Upton offered to buy him a drink, which was an indication that she is open to reconciling with him.
Halstead Takes Accountability For What He Did To Upton, But Will It Work?
Admittedly, it would have been unwise to expect that the 2026 One Chicago crossover could properly fix Upton and Halstead’s complicated situation. While seeing them come back is exciting, the TV special still had other storylines to tackle, given the sheer number of characters it had to juggle, not to mention a central mystery to solve. Still, seeing Halstead finally coming to his senses and do the bare minimum by apologizing to his ex-wife was gratifying, especially considering how much Upton suffered after what she did to her.
Whether his seemingly earnest speech would be enough to convince Upton to give him another chance is unclear. The 2026 One Chicago crossover made it clear that they still care for each other, but that doesn’t guarantee that she would be open to taking a risk again with him. After the initial wall broke down, Upton had been very gracious with how she treated Halstead. Until the very end, she told him that she would always wish him the best. That’s a very normal reaction to someone whom you once loved dearly.
One Chicago 2026’s Crossover Changes Its Winning Formula For The First Time Ever
New details about the 2026 One Chicago crossover confirms that NBC is changing its winning formula for the special for the first time in its history.
Halstead is lucky that Upton isn’t furious at him — a totally justified reaction after how much pain he inflicted upon her just because of his inability to process his own existential crisis. Up until his brief but meaningful conversation with Voight at the end of the three-hour event, it seemed like he was ready to blame his old boss for playing a part in their separation. What he didn’t know was on the heels of his departure, Upton and Voight grew closer and made each other better.
If Halstead stands a chance at winning back Upton, he needs to do more than just apologize. The last time that they were together, he made promises that he eventually walked back on, so it makes sense that Upton isn’t keen on believing him right away. To be fair, it did seem like he was willing to do more than just deliver an earnest speech. When asked what time his flight was outside of Chicago, Halstead said that he didn’t care about it, implying that he was ready to drop everything else if it meant being able to spend time with Upton.
What Are The Chances Of Halstead & Upton Returning To One Chicago Again?
At this point, there is no word about either Soffer or Spiridakos coming back for future episodes of Chicago PD season 13. Soffer recently wrapped up his time as Wesley Mitchell in Dick Wolf’s CBS spinoff, FBI: International. Meanwhile, Spiridakos is set to spearhead her very own show on USA Network, playing the titular character in Anna Pigeon. The good thing is that both of them have clearly maintained a good relationship with their former One Chicago co-workers, so it shouldn’t be difficult to invite them back, if they are needed for another story.
It is unfortunate that the 2026 One Chicago crossover didn’t spend more time with Upton and Halstead after the case was solved. It would have been nice to see them in a more relaxed setting after she invited him for drinks. Nonetheless, leaving them on a positive note was so much better than how their relationship was left hanging when both of them exited Chicago PD. Considering the circumstances of both the procedurals and the actors, the chances of the show showing any kind of reconciliation between them are small to none.
Ultimately, if this is the last time that both of them will appear in One Chicago, it’s a great send-off for both Spiridakos and Soffer — although more so for him than her. However, if NBC and Wolf Entertainment decide to bring them back again, it would be hard-pressed to find anyone who would be against it.
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6/10
- Created by
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Derek Haas, Michael Brandt
- First Episode Air Date
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October 10, 2012
- Cast
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Jesse Spencer, Taylor Kinney, Monica Raymund, Jason Beghe, Jon Seda, Sophia Bush, Jesse Lee Soffer, Nick Gehlfuss, Yaya DaCosta, Torrey DeVitto, Rachel DiPillo, Philip Winchester, Joelle Carter, Monica Barbaro, Carl Weathers, Yuri Sardarov