The Best 5 One Chicago Couples Of All Time

The “One Chicago” franchise, like any other successful entertainment endeavor, is ultimately all about conveying emotion. This cavalcade of Windy City first responder shows is better equipped for the task than most, too. The dangerous lives of the firefighters on “Chicago Fire,” the police detectives on “Chicago P.D.,” and the medical professionals on “Chicago Med” provide ample material for the sort of thrills and spills any procedural drama worth its salt thrives upon. This may very well be part of why the three shows’ short-lived spin-off sibling “Chicago Justice” failed. After all, how could a legal drama effectively reproduce the “One Chicago” franchise’s signature adrenaline rushes week in and week out?
Of course, dangerous missions are just one part of the franchise’s tool kit for eliciting emotion, and not necessarily even the most effective one. Surprising character departures and deaths — say, Brian “Otis” Zvonecek’s (Yuriy Sardarov) death in the Season 8 premiere — are effective for shock moments and cliffhangers, sure. However, the “One Chicago” shows have long established that the biggest wrench among their audience enticement tools is love. The characters indulge in a truly mind-boggling amount of workplace romances, which have become an integral part of the franchise’s makeup. Fans are loving this aspect of the shows, too, coming up with their own little portmanteaus of the involved characters’ names and following their stories with keen interest. Here’s a look at five of the “One Chicago” franchise’s most impactful and important couples.
Jay Halstead and Hailey Upton (Chicago P.D.)

There’s something to be said about taking things slow. “Chicago P.D.” outright weaponized this approach with Jay Halstead (Jesse Lee Soffer) and Hailey Upton (Tracy Spiridakos), two detectives who go from somewhat uneasy partners to passionate lovers … but the show sure takes its sweet time cooking up this particular delicacy.
The “Upstead” story kicked off in “Chicago P.D.” Season 4, when the pair were partnered together after Halstead’s previous romantic partner, Erin Lindsay (Sophia Bush), broke up the “Linstead” couple and headed off to join the FBI. Halstead, in a predictably rotten mood, did his level best to keep Upton at arm’s length and then some — but of course they eventually ended up growing closer. First, it was only as partners, but the “One Chicago” shows love a good romance, so it was only a matter of time before the two ended up together.
Here’s the magic trick, though: “Chicago P.D.” absolutely did not rush the story here. Instead, Halstead and Upton grew a little bit closer every season, taking until Season 8 to explore the next step in their relationship. Because viewers have followed this inevitable but molasses-paced arc for years, their big kiss in Season 8, Episode 3 (“Tender Age”) was a candidate for the finest romantic payoff in the entire franchise. Bonus points for Upton rejecting an FBI job offer soon afterward, as if to underline that the couple’s bonds now run deeper than Halstead and Lindsay’s ever did.
Daniel Charles and Caroline Charles (Chicago Med)

The “One Chicago” franchise doesn’t reserve all its romances for 20- and 30-somethings. As Dr. Daniel Charles (Oliver Platt) and Caroline “CeCe” Charles (Paula Newsome) readily prove, “Chicago Med” has had little problem allowing the somewhat more senior members of its stacked cast to get busy — albeit with a sense of tragedy and finality that’s a far cry from many other memorable moments from the show.
In many ways, Dr. Charles and CeCe are a far more charming couple than what’s generally seen as the main “Chicago Med” item, Dr. Will Halstead (Nick Gehlfuss) and Dr. Natalie Manning (Torrey DeVitto). While Will and Natalie’s story was exactly the sort of long-gestating will-they-won’t-they the franchise is so good at, the “One Chicago” shows have used this formula many times. Dr. Charles and CeCe, on the other hand, offered the viewer a unique story of two divorcées who find each other again in the most tragic circumstances possible.
After quite some time apart, the pair reconnected in “Chicago Med” Season 4, when CeCe became a lymphoma patient at the Gaffney Chicago Medical Center. As it turned out, Dr. Charles and CeCe still had feelings for each other, and as their love lit up anew, they got married again. Unfortunately, however, CeCe’s illness was terminal. Determined to do what he can to make her final days as happy as possible, Dr. Charles made arrangements for CeCe to say goodbye to everyone she loves and also to spend some personal time with her one last time. Their romantic arc, which began in Season 4, Episode 15 and ended in Season 5, Episode 9, technically didn’t even last for a full season … but boy, did Platt and Newsome know how to supercharge every single moment of it.
Matt Casey and Sylvie Brett (Chicago Fire)

When their story got going, Matt Casey (Jesse Spencer) and Sylvie Brett (Kara Killmer) became a freight train of inevitability. Out of professional and personal respect toward each other, “Brettsey” did their level best to keep things platonic for quite a while before the weight of the narrative overwhelmed their intentions. What’s more, a combination of the “Chicago Fire” pair’s hesitance and behind-the-scenes events enabled the show to add surprisingly many shades of drama to their love story.
The slow burn of the characters getting together was as well-executed as “One Chicago” ever is. “Brettsey” combined this leisurely pace, with both characters existing (romantically) independently of each other for a good while before the show started teasing the relationship: Casey is a “Chicago Fire” original, while Brett joined Firehouse 51 in season 3. Yet, their prospective romance didn’t come into play until Season 7, and even then, it initially played out as a deepening friendship. Not that the show particularly bothered to hide the writing on the wall: Casey is the show’s de facto romantic lead, with relationships between both Hallie Thomas (Teri Reeves) and Gabriela Dawson (Monica Raymund), so it wasn’t terribly hard to gauge what was up when Casey and Brett started bonding after “Dawsey” (who also just so happened to start as friends) fell apart.
The next twist came just as Brettsey was running at a fever pitch. Spencer left “Chicago Fire” in Season 9, leaving the fate of the pair legitimately up in the air. Ultimately, things played out nicely enough: Casey became a recurring character while Killmer’s Brett did the heavy lifting to keep the bumpy romance arc going. Brett and Casey eventually got married in Season 12 and, with this happy ending, the characters left Chicago for greener pastures.
Adam Ruzek and Kim Burgess (Chicago P.D.)

Kim Burgess (Marina Squerciati) and Adam Ruzek (Patrick John Flueger) are the poster couple for the “One Chicago” way of handling romantic relationships. “Burzek” are effectively the Ross (David Schwimmer) and Rachel (Jennifer Aniston) of the franchise: Their romantic potential was obvious to the audience from the very beginning, they went through a series of crises that they nevertheless invariably (and sometimes inexcplicably) got over, and their path together, while full of ups and downs, ultimately led to happiness.
Flirting; kissing and pretending that nothing ever happened; getting briefly engaged in “Chicago P.D.” Season 3; Burgess and Ruzek already gave the viewers a generous greatest hits collection’s worth of serial drama romance in the early stages of their journey. Even when they didn’t actively date during Season 5 and Season 6, the tension was there, and all the other developments in their personal and romantic lives couldn’t help but seem like placeholders. This made their eventual (and very, very bumpy, thanks to the famous miscarriage storyline) road back together in Seasons 7 and 8 all the more emotionally impactful.
While their relationship remained turbulent even after they adopted Makayla (Ramona Edith Williams), by this point, it’s clear that absolutely nothing short of an unimaginable tragedy would tear Burgess and Ruzek apart — and that every time they hit a bump on the road, they would return stronger than they ever were. Arguably the most battle-tested romance in the “One Chicago” franchise, “Burzek” only narrowly loses the No. 1 spot on this list because their relationship is more akin to a long-running side plot than it is to a show-hijacking event — which is precisely what our winning couple happens to be.
Kelly Severide and Stella Kidd (Chicago Fire)

“Stellaride” is likely the most famous relationship portmanteau the “One Chicago” franchise has to offer, and it’s not just because it rolls off the tongue nicely. “Chicago Fire” mainstays Kelly Severide (Taylor Kinney) and Stella Kidd (Miranda Rae Mayo) have gone through thick, thin, and thick again over the years to establish themselves not just as a focal point of the cornerstone show of the “One Chicago” universe, but as the couple all others in the franchise are measured against.
The thing that puts this couple head and shoulders above the competition is their no-frills approach. The two are both firefighters in a show that focuses on and glorifies firefighters, so they’re on equal footing. Severide is a heroic professional and a trusted colleague among the Firehouse 51 personnel, but romantically, he’s the classic “womanizer who ends up settling down when he finds the right girl” archetype — in other words, a perfect character for a workplace romance in a procedural drama. Kidd is a recent divorcee who’s amazing at her job, but who has a tomboyish laissez-faire attitude toward her personal life. A fun misunderstanding prior to the show’s events (not to mention Kidd’s divorce) led to an embarrassing encounter that immediately established an awkward chemistry between the pair, and boy, has “Chicago Fire” done a great job building from that starting point.
Over the seasons, Severide and Kidd not only established a solid relationship, but the argument could also be made that the entire “Chicago Fire” eventually started to lean on their romance, which thus became the steely backbone of the flagship show in the franchise. With both characters still in active service, there’s no telling where their story will take the viewers … but wherever it is, expect fireworks.





