Between Chicago Fire and spinoffs Chicago P.D. and Chicago Med, there is no shortage of romance in the Windy City. From “Burzek” to “Manstead” to “Stellaride,” the #OneChicago franchise is full of mash-up couple names — and some pairings that simply can’t be contained in a hashtag.
Over the years, we rooted for P.D.’s Halstead and Lindsay, and Fire‘s Casey and Gabby, as they fell in love. But life is full of unexpected surprises and challenges, and now we find ourselves falling for some new romances, right alongside the show’s leading men. But not every love story is a winner: Some past relationships have left a sour taste in our mouths with time, while others were doomed from the very start.
TVLine reviewed #OneChicago’s many couplings, past and present, and sorted them from worst to best. But first, some criteria rules: One-episode flings/hookups and non-starter flirting that didn’t go anywhere don’t count, so sadly, a certain PD cop didn’t make the cut at all. (#AtwaterDeservesLoveToo!) And you won’t find Burgess’ mostly unseen boyfriend Matt Miller, who only appeared in one installment, on this list either.
Check out our rankings below to find out which couple is No. 1 in our hearts, then hit the comments with your own fave pairs — and those that missed the mark.
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Natalie and Phillip, Chicago Med
Image Credit: NBC screenshot It’s a shame that Phillip turned out to be a liar who manipulated Natalie into thinking they got engaged before she lost her memory, because Torrey DeVitto and Ian Harding’s real-life friendship gave the Pretty Little Liars vets a nice foundational chemistry. And as widows with young kids, the characters made sense as a couple. But there’s just no excuse for Phillip’s completely unacceptable behavior.
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Halstead and Camila, Chicago P.D.
Image Credit: Courtesy of NBC The detective hooked up with Camila while undercover and then continued to carry on a relationship with her even after the case was over, all while lying to her about his real identity. Oh, and she was lying to him about her drug-dealing ways. Needless to say, this was no fairy tale.
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Tate and April, Chicago Med
Image Credit: Courtesy of NBC His constant remarks about wanting her to quit her job were a big turn-off. (April’s no little lady!)
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Hannah and Will, Chicago Med
Image Credit: Courtesy of NBC Considering they met at an underground clinic where Will treated Hannah’s addiction to drugs, we shouldn’t be surprised at the number of rules that this pairing broke, like continuing to date through her recovery, despite Dr. Charles’ warning. When Hannah left the Windy City for a fresh start in LA following a relapse, it was truly for the best.
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Connor and Sam, Chicago Med
Image Credit: Courtesy of NBC More competitive rivals than partners, the surgeons’ relationship was destined to fail. And so it did.
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Mackey and Gallo, Chicago Fire
Image Credit: Courtesy of NBC Perhaps Gallo should have listened when Cruz warned him against dating Mackey. When her portrayer Adriyan Rae left the show after just nine episodes, their brief dalliance was over before you could say “hookup” and before we could actually get invested in the twosome.
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Hallie and Casey, Chicago Fire
Image Credit: Courtesy of NBC Before marrying Gabby, the firefighter was engaged to physician Hallie, who was tragically murdered, leaving behind a devastated Casey. But we can’t say that we were too heartbroken that their story was cut short.
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Brett and Cruz, Chicago Fire
Image Credit: NBC screenshot She needed a man, and the firefighter, while a good-hearted guy, was a tad on the man-child side at the time. Plus, their breakup gave Cruz time to mature and find his perfect match in rescue victim Chloe.
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Zach and Stella, Chicago Fire
Image Credit: Courtesy of NBC What a refreshing change of pace it was to see Stella let her hair down and turn her attention to someone who wasn’t Severide. But of course, her relationship with handsome hazmat officer Zach eventually fell apart, paving the way for the rescue squad lieutenant to win Stella’s heart.
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Sarah and Joey, Chicago Med
Image Credit: Courtesy of NBC What started out as a sweet, supportive workplace romance ended so abruptly, we’re still trying to figure out what happened.
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Clarice and Shay, Chicago Fire
Image Credit: NBC screenshot We were all for Shay finding love with Clarice, even after the brunette came back pregnant with her ex-husband’s baby. But Clarice’s constant stringing along of Shay finally took its toll when she decided to give into her former spouse’s demands and move to New York to maintain custody.
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Will and Sabeena, Chicago Med
Image Credit: Courtesy of NBC While the relationship started out well enough, Will quickly mucked things up by going behind Sabeena’s back and compromising her medical trial. Plus, is it just us or did she seem more interested in Ethan?
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Vicki and Ethan, Chicago Med
Image Credit: Courtesy of NBC Truthfully, the vets’ connection wasn’t fully explored before Vicki vanished, which is a shame because the pairing had lots of potential.
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Nina and Will, Chicago Med
Image Credit: Courtesy of NBC Cute as they were, Nina deserved better than a guy who the entire hospital knew was hung up on Natalie. And yet, this might have been Will’s healthiest relationship?!
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Mills and Gabby, Chicago Fire
Image Credit: NBC screenshot The show did its best to distract viewers from the inevitable “Dawsey” coupling with this affable pairing. But trust issues on Mills’ part and Gabby’s inability to assure him that she didn’t still have feelings for Casey doomed their relationship.
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Connor and Ava, Chicago Med
Image Credit: Courtesy of NBC The surgeons’ competitive spirit eventually gave way to a promising romance that failed to live up to its potential. Things got seriously twisted, first when it was implied that Ava had sex with Connor’s father to get funding, and then when she led Connor to believe that his dad was spreading a rumor about them sleeping together. When that manipulation didn’t work, Ava gave his father a lethal dose of insulin so that she and Connor could be together, before eventually killing herself. This was one messy relationship that was written into an unfortunate corner that no one could get out of unscathed. (Even Connor had to leave Med for a fresh start after the whole ordeal.)
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Kyle and Brett, Chicago Fire
Image Credit: Courtesy of NBC The CFD chaplain was a sweet fiancé to Brett, but life in Indiana with Kyle proved to be too dull and safe for the paramedic. You could say there just wasn’t any fire between the two characters.
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Eric and Ritter, Chicago Fire
Image Credit: NBC screenshot It’s so very nice to see a (semi) stable LGBTQ couple in the #OneChicago universe. And now that they’ve reconciled following a short quarantine-fueled split, can we please get some more Ritter and Eric scenes?
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Grainger and Brett, Chicago Fire
Image Credit: NBC screenshot Grainger totally could have been The One. Fun, sweet and handsome, the firefighter seemed to have it all — except for Brett’s heart, which belonged to Casey.
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Blair and Burgess, Chicago P.D.
Image Credit: NBC screenshot Why was Burgess planning to break up with the political consultant? Has she seen Charles Michael Davis?! Before Burgess could call off a perfectly good relationship, which even she admitted “could’ve been something truly amazing,” Blair was tragically killed.
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Renee and Severide, Chicago Fire
Image Credit: Courtesy of NBC When Severide wouldn’t give up his career to move to Madrid with the international finance lawyer, that pretty much said it all. Then she came back preggers, believing and wanting the baby to be Severide’s. (Can you blame her?) Unfortunately, you can’t always get what you want, as Renee learned when she returned yet again to get Severide’s help with a case and planted a kiss on him, which only drove him into Stella’s arms.
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Otis and Katie, Chicago Fire
Image Credit: NBC screenshot Remember when Otis dated Severide’s sister? The adorkable couple bonded over a game of Catan. How can you not love that?
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Roman and Burgess, Chicago P.D.
Image Credit: Courtesy of NBC The partners definitely hit it off, but let’s be honest: He was way more into her than she was into him, as evidenced by Burgess’ decision not to move to San Diego with Roman.
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Casey and Naomi, Chicago Fire
Image Credit: Courtesy of NBC After working together on a case, the investigative journalist became Casey’s first significant romance after his divorce, allowing him to finally move on and have some fun. And the more we get of Casey smiling (and fighting fires in his PJs), the better!
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Connor and Robin, Chicago Med
Image Credit: Courtesy of NBC Connor’s devotion to his girlfriend during her illness was admirable. However, we didn’t sign up to watch him play caretaker, and neither did Robin. But looking back, maybe these two gave up on each other too soon?
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Natalie and Jeff, Chicago Med
Image Credit: Courtesy of NBC Although it was obvious that Natalie was going to get together with Will, silver fox Jeff was a pretty charming love interest who felt like more than just a placeholder. (But yes, it was a little weird that he shared a first name with her deceased husband, who was also his best friend.)
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Gallo and Violet, Chicago Fire
Image Credit: NBC screenshot Gallo is a bit out of his depth when it comes to the opposite sex, especially so with Violet, whom he randomly proposed to mid-argument! But if there’s anyone that can handle that chaotic energy and keep Gallo on his toes, it’s the tough, whip-smart paramedic.
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Ruzek and Upton, Chicago P.D.
Image Credit: Courtesy of NBC Talk about being blindsided! The unexpected pairing seemed to come out of nowhere, and with their very different personalities and policing philosophies, Ruzek and Upton were too mismatched to really last. Plus, they were both obviously hung up on someone else.
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Lily and Otis, Chicago Fire
Image Credit: NBC screenshot Before Otis met his tragic fate — which we’re still not over, FYI! — he met and fell for the cute co-owner of Molly’s North. After Otis’ death, Lily was so heartbroken that she turned the bar into a bakery because it reminded her too much of her beau. Sniff! But we’re glad Otis experienced real love before he died.
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Natalie and Will, Chicago Med
Image Credit: Courtesy of NBC We were rooting for the docs during the show’s early seasons, when it was clear that they were smitten with each other and were bound to make the inevitable leap from pals to something more. But when it took Natalie a week to answer Will’s proposal, that was just the first of many red flags that made it clear these two were a healthier pairing as just friends.
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April and Ethan, Chicago Med
Image Credit: Courtesy of NBC The on-and-off pair got so far as to move in together and get engaged, but tensions over his sister Emily, struggles to get pregnant and a secret kiss with Crockett drove a wedge between the couple. Sure, April told Ethan she loves him in the recent Season 6 finale, but with Yaya DaCosta leaving the show, we don’t have much hope for them healing their issues.
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Severide and Lindsay, Chicago Fire/P.D.
Image Credit: Courtesy of NBC The characters seemed so perfectly suited to each other: Both are fierce, determined and tough as nails. But too much of the same makes it hard to grow together, as we learned from one of the franchise’s first crossover couples.
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Charles and Caroline, Chicago Med
Image Credit: Courtesy of NBC The former husband and wife found their way back to each other and even got remarried, but their reunion was cut short by Caroline’s cancer. With the time they had left together, Charles and CeCe made the most of their second chance at love.
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Severide and Brittany, Chicago Fire
Image Credit: Courtesy of NBC Although Severide has had longer relationships, his quickie Vegas marriage to graphic designer Brittany is still a memorable one. Both characters were struggling with the loss of a loved one, so what started off as a potentially disastrous idea — getting hitched to a stranger on a whim? Come on! — actually became so moving and emotional that even their split was romantic.
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Severide and Anna, Chicago Fire
Image Credit: Courtesy of NBC The firefighter wanted to do something good with his life, and he found the purpose he needed in leukemia patient Anna. Not only did he donate his bone marrow to her sans anesthesia (!!!), but he also fell in love with Anna. Sadly, she still succumbed to her illness as the too-sweet-to-live relationship hit all of our favorite romantic drama tropes.
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Natalie and Crockett, Chicago Med
Image Credit: Courtesy of NBC During their brief romance, Natalie brought out an unexpectedly tender side of the so-called womanizing Crockett, who opened up to her about the tragic loss of his daughter. And for once, Natalie seemed to be in an easygoing, (mostly) drama-free relationship. We definitely wouldn’t have minded if these two had continued to date, but alas, they broke up ahead of Torrey DeVitto’s exit from the show.
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Antonio and Brett, Chicago P.D./Fire
Image Credit: Courtesy of NBC We never would have predicted a romance between these two — they’re just so different — but therein laid their appeal. He brought out a less innocent side of the paramedic, while she made him more vulnerable.
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Maggie and Ben, Chicago Med
Image Credit: Courtesy of NBC Sometimes, the best things come about during the worst times in life. Such was the case for Maggie and Ben, who met while both were going through chemotherapy. After a close call for Ben, the couple celebrated their miraculous second chance at life with a wedding in the 100th episode. Although their attempt to adopt and start a family didn’t go to plan, Ben’s support and understanding through all the complications proved that Maggie chose the right fella for her.
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Cruz and Chloe, Chicago Fire
Image Credit: NBC screenshot Wisdom says a firefighter shouldn’t fall for his rescue victim, but when the resulting couple is as charming as Joe and his wife Chloe, you gotta make an exception. And after getting his heart broken by Brett — and still being a standup guy in the aftermath — there’s no one more deserving of finding happiness than the lovable firefighter.
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Boden and Donna, Chicago Fire
Image Credit: Courtesy of NBC Chiefs deserve happiness, too. Thankfully, Boden found love — and surprise fatherhood — with the school teacher, who more than holds her own against her hubby’s commanding presence.
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Brett and Casey, Chicago Fire
Image Credit: Courtesy of NBC Both hurting from the departure of Gabby, Casey and Brett found comfort in each other as friends, first and foremost. But with time, it became obvious that they also shared an attraction, one that was only just recently consummated. So we have yet to truly see the pair as a real couple — time will tell if this twosome moves up in the rankings — but judging by that steamy sex scene, maybe they have more sizzle than they let on?!
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Halstead and Upton, Chicago P.D.
Image Credit: Courtesy of NBC Several seasons of slow-played pining made the partners’ first kiss and subsequent relationship feel oh so earned. Watching the pair finally confess their feelings and say “I love you” to each other felt like we’d gotten a prize for being patient. But we’ve got some concerns about the fact that Upton is keeping a few very important truths from her beau, and depending on how her jarring proposal plays out, the couple could easily move up or down this list.
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Halstead and Lindsay, Chicago P.D.
Image Credit: Courtesy of NBC Their love for each other can’t be denied, but man, they had baggage. So. Much. Baggage. In an ideal world, the ex-couple would have found their way back to each other years later, after figuring out their own issues. Alas, Sophia Bush departed the series, leading Halstead to eventually find love with a new partner.
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Gabby and Casey, Chicago Fire
Image Credit: Courtesy of NBC From the show’s early episodes, the colleagues had “OTP (One True Pairing)” written all over them, and for a while, they were the show’s golden couple during their (many) ups and downs. But their marriage came to an end when Monica Raymund left the drama after six seasons. However, the power of Casey and Gabby’s connection lives on even in the wake of their divorce, as evidenced by the chemistry that still burned between them when she came back for a brief visit.
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Burgess and Ruzek, Chicago P.D.
Image Credit: Courtesy of NBC What a rollercoaster “Burzek” has been! The former couple called off their engagement as a result of Ruzek’s commitment issues, but their feelings for each other have never gone away. Over the seasons, the pair have casually hooked up, almost had a baby together and, most recently, started to form a makeshift family with Burgess’ adopted daughter. Even when things get difficult or Burgess pushes Ruzek away or new significant others come into the picture, the exes’ enduring love for each other shines through. So eight seasons later, we’re still ‘shipping them something fierce.
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Severide and Stella, Chicago Fire
Image Credit: Courtesy of NBC What started as a casual thing is now one of the most stable, supportive and loving relationships in the #OneChicago universe. “Stellaride” has put viewers through a lot of ups and downs, but once Severide told his gal, “I decided I’m going to be the man you deserve,” we were goners. As both characters have grown, individually and together, the recently engaged couple has matured into a place of true commitment. Here’s to a wedding in Season 10!
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Platt and Mouch, Chicago P.D./Fire
Image Credit: Courtesy of NBC The only cross-show couple to make it work thus far — they even got married! — the tough Platt and teddy bear-like Mouch are the definition of relationship goals. Best of all? We never have to worry about them breaking up because they’re solid as a rock.
