Why Chicago P.D.'s Big Twist For Upton And Halstead Isn't Too Soon

chicago pd season 8 upstead halstead and upton
(Image credit: NBC)

MAJOR SPOILERS AHEAD for the winter finale of Chicago P.D. Season 9, called “A Way Out.”

Chicago P.D. spent most of the first half of Season 9 with the threat of Upton and Voight’s big secret getting out to the wrong people, with Halstead dragged into the mess after connecting dots about Roy’s death. After FBI Agent North gave Halstead an ultimatum that he’d have to either flip on Voight or he and Upton would go to prison, he found a third option in the winter finale. He had to cross some lines and abandon ethics to pull it off, but he was willing to do what it takes to protect his family, which included Upton. And now, after the final scene of “A Way Out,” Upstead are family in a legally-binding sense, because they got married!

Yes, after an intense hour with the threat of major characters going to jail hanging over the case of the week, Jay Halstead delivered the third Upstead proposal, but this time asking Hailey Upton to marry him ASAP. And they did! In a sequence that intercut their courthouse wedding with consummating the marriage at home, they took the biggest step forward… less than a year after their first kiss episode aired back in January 2021. Under most circumstances, going from the first official step forward to married in under a year would seem way too fast, but I think it works for Upstead. Here’s why.

They Were Already Partners For Years

Is it fast for a couple to get married after eleven or so months of a relationship? Yes, but arguably not too soon for Upton and Halstead, mostly because they’ve been partners and friends for a long time. Even though they didn’t click right away after being partnered up in early Season 5, they grew very close long before Halstead was shot and Upton had to face that she loved him as more than partner and friend. The romantic relationship is pretty new; the close and loving relationship is not. Plus, if their relationship could survive the Roy situation, I’d say they can handle just about anything. 

The Wedding Was Spontaneous

If they had gotten married in the midseason finale after spending the first half of Season 9 planning their nuptials in the same elaborate way that One Chicago’s other Halstead was during his brief engagement, I 100% would have thought it was rushed. After all, I cringed when Upton proposed in the Season 8 finale because it was so soon and they clearly hadn't really talked about marriage. With this wedding, they made the decision after months of engagement because the threat that had been hanging over their heads all season was finally gone, they loved each other, and there was nothing to stop them. The spontaneity makes it feel like a decision that they just made for themselves because they wanted to be married. They didn’t overthink it, so it makes sense. 

It Was Very Them

I’ve been a fan of Upton and Halstead’s relationship after watching them grow from partners and friends, but ever since Upton popped the question at the end of Season 8, I just haven’t been able to picture these characters dressed to the nines for a big wedding with a crowd of friends and family attending. They’ve been so understated and private with their relationship in front of others that it just seemed like something smaller made more sense. 

Plus, when would they have time to have a traditional wedding with their jobs? If anything, more characters in One Chicago should elope if they ever want to have the time to tie the knot. At the end of the day, it felt very them that they’d put on some nice but not formal clothes, head to the courthouse, and just get married. I’m not sure that I could see it happening like this for many others in One Chicago, but it worked for Upstead.

Bonus: Upton Isn’t Pregnant (Probably)

I’ve had the irrational fear all season that Chicago P.D. would deliver an Upstead pregnancy just to add a new wrinkle to all the complications, and pregnancy rarely goes well for the women of One Chicago even at the best of times. If they had rushed to the altar because she was pregnant, or that was part of the equation, their wedding just wouldn’t have felt like it was fully about wanting to marry each other. Now, P.D. is heading into a whole new era for multiple reasons, and I’m looking forward to seeing what happens next. 

And what can I say, other than that both of these characters have gone through hell and back, and that I’m all for them getting married if it makes them happy? There’s not enough smiling or happy endings on Chicago P.D., and that’s what the end of the midseason finale delivered. Find out whether or not they get to keep on being happy together with the winter premiere of Chicago P.D. Season 9 on Wednesday, January 5 at 10 p.m. ET on NBC, following the winter premiere of Chicago Fire at 9 p.m. ET to follow up on the Stellaride cliffhanger and Chicago Med at 8 p.m. ET with its own development for Will Halstead.

Laura Hurley
Senior Content Producer

Laura turned a lifelong love of television into a valid reason to write and think about TV on a daily basis. She's not a doctor, lawyer, or detective, but watches a lot of them in primetime. Resident of One Chicago, the galaxy far, far away, and Northeast Ohio. Will not time travel, but will sneak references to The X-Files into daily conversation.