One Chicago’s five best couples on Valentine’s Day 2020
By Kari Highman
One Chicago fans can celebrate Valentine’s Day with our favorite Chicago Fire, Chicago PD and Chicago Med couples from the current season.
It wouldn’t be Valentine’s Day without our favorite One Chicago couples. A huge part of what makes One Chicago so fun to watch are the “ships” of each show. From those currently coupled up to the ones we’re still waiting to see get together, Chicago Med, Chicago Fire, and Chicago PD have no shortage of romances. But which couples have been the best this season?
One Chicago fans have seen the demise of a few long-lasting relationships, but at the same time, some couples have flourished. Their ups and downs are all a part of the emotional rollercoaster viewers get to enjoy every week—and also a reason why the One Chicago fandom is so popular, especially on social media.
Below are five couples—three of which are currently together, one of which is technically together, and one that the writers seem to be pushing for—that have caught our attention this season. See if your favorite Chicago Med, Chicago Fire or Chicago PD pairing made our list!
5. Jay Halstead and Hailey Upton, Chicago PD
Last but certainly not least is the could-be One Chicago couple from Chicago PD. The partnership of Detectives Jay Halstead (Jesse Lee Soffer) and Hailey Upton (Tracy Spiridakos) has long been met with the question of “Will they, or won’t they?”
Over the last two years, these two have gone from partners, to friends, to something a little more so. Fans were watching Halstead and Upton’s looks at each other and taking notice of “the thing that works” between them—their long conversations after tough cases.
These little things implied that something was bubbling underneath the surface for the two of them, but up until Chicago PD season 7, we hadn’t seen it voiced from either side. Now it seems clear that the writers are planning for them to be the next One Chicago pairing.
In the midseason premiere “Mercy” newcomer Vanessa Rojas (Lisseth Chavez) got Hailey to open up a little bit about her relationship with Jay, whose fate was still unknown after he’d been shot at the end of the previous episode.
“It’s hard because you love him,” Vanessa told Hailey. “Of course I love him, he’s my partner,” Upton replied. But toward the end of the episode, we saw Hailey almost tell Jay her true feelings. She realized that she could have lost him again, and if she didn’t tell him soon, she might never have the chance.
Yet In true TV fashion, a phone call interrupted the emotional moment between them and made Hailey pull back. She has since bottled up her emotions, but we saw Halstead’s come out a little bit in “The Devil You Know” when he confronted Hailey about her dealings with Darius Walker (recurring guest star Michael Beach). He followed her—just as he said he’d “follow her anywhere” in “Informant”—and told her that whatever she was doing, it concerned him.
This continues their pattern of sticking by each other no matter what when trouble has arisen, much like they did last season in “Outrage” or during season 5 in “Ghosts.” While these two might not be a couple yet, there have been certain moments that really make One Chicago fans wish they were.
Upstead has a great foundation to build on; only time will tell if one of them makes the first move and confesses romantic feelings before Chicago PD season 7 ends. One Chicago likes to leave us guessing, so these two may get together when we least expect it, but they absolutely ought to be together.