Over the course of theOne Chicagofranchise’s 35 seasons (not includingChicago Justice),there have been 12 weddings.Unfortunately, not all of them ended in happily ever afters. One wedding didn’t even get to the “I do’s.” Nevertheless, love has been at the center ofeveryOne ChicagoTV show—Chicago Fire,Chicago PD, andChicago Med— meaning there have been plenty of nuptials to go around the Windy City.
NBC renewed all threeOne Chicagoseries in May 2025, andChicago Fireseason 14,Chicago PDseason 13, andChicago Medseason 11 will premiere in the fall of 2025 (perDeadline).
SincetheOne Chicagouniverseseemingly keeps expanding, we will likely have even more weddings to discuss and rank in the future. New romances pop up in Firehouse 51, the Intelligence Unit, and Gaffney Chicago Medical Center almost every season. Plus, some current couples in the procedural shows could get married in the future. For now, though,the popular NBC franchise contains many relationships that ended with the two characters walking down the aisle— 12, to be exact.
12Natalie & Will
Chicago Med Season 4, Episode 9
As mentioned above,aOne Chicagowedding ended prematurely,and that wasNatalie Manning and Will Halstead’s inChicago Medseason 4. The two characters' relationship could only be compared to a rollercoaster, and just when it felt like they could finally get a win, it was taken away from them. Instead of saying “I do,” the Burke family comes after Will, and the doctor ends up going into protective custody.
The good news is thatWill and Natalie managed to get their happy ending inChicago Med.It just took them eight seasons to get there.Nick Gehlfuss leftChicago Medafter season 8, and the finale concluded with his character leaving Gaffney Chicago Medical Center, moving to Seattle to reconnect with Natalie.
11Maggie & Ben
Chicago Med Season 5, Episode 17
Unfortunately, Maggie Lockwood and Ben Campbell’sromance inChicago Medcertainly wasn’t the most memorable relationship in theOne Chicagofranchise, let alone in their own show. Their story was sweet, though. And it was satisfying to see Maggie happy on her wedding day (despite it taking place in a bowling alley). However,Maggie and Ben’s marriage ended in a divorce in season 9,which is part of the reason why their wedding is ranked low.
10Charles & CeCe
Chicago Med Season 4, Episode 22
Dr. Daniel Charles reconciling with his ex-wife, Caroline “CeCe” Charles inChicago Medseason 4 was one of the show’s most bittersweet stories. Yes, it was heartwarming to watch the two lovebirds wed again. Their Hawaiian-style nuptials were quite special. But,one couldn’t help but feel at least a little bit of sadness when Charles and CeCe said, “I do,“knowing that CeCe was dying from lymphoma. She ultimately passed away in season 5.
Chicago PD Season 9, Episode 9
While Jay Halstead and Hailey Upton are, without a doubt, one of the most popular romances in theOne Chicagouniverse,their wedding lacked excitement.It was a last-minute decision and featured none of their loved ones. Perhaps it went hand-in-hand with their relationship, but it was still a little disappointing. Nevertheless, the greatness of Halstead and Upton’s love story was enough to make their courtroom wedding worthwhile (even ifHalstead and Upton ultimately broke up inChicago PDseason 10).
8Burgess & Ruzek
Chicago PD Season 12, Episode 22
Chicago PD’s Kim Burgess and Adam Ruzek’s weddingin the season 12 finale is the latest in a flurry ofOne Chicagoweddings, and similar to Halstead and Upton’s, it was disappointing.We didn’t get to hear Burgess and Ruzek’s vows,and the episode featured very little of the actual ceremony. After 12 seasons of a will-they/won’t-they slow burn, the audience deserves a more satisfying ending. However, Burgess and Ruzek are iconic enough to warrant a higher placement. It also helps that other characters attended the wedding.
7Boden & Donna
Chicago Fire Season 2, Episode 22
(Former) Chief Wallace Boden and Donna Robbins hadone of the healthiest relationships in theOne Chicagofranchise.They were surely the most stable oftheChicago Firerelationships. So, it was quite exciting to see them tie the knot. While Boden and Donna’s ceremony was about as perfect as any wedding could get, it ended in disaster as the characters faced an awful tragedy.
Unfortunately, during the season 3 premiere, viewers learned that Leslie Shay had died, which didn’t make for the perfect ending to Boden and Donna’s wedding story.
After Boden and Donna exchanged vows,Firehouse 51 was called to a fire towards the end of theChicago Fireseason 2 finale.After arriving, the firefighters and paramedics headed inside, while Boden waited outside. The chief lost communication with his team, and the building exploded. The episode ended with the audience unaware of the fates of almost everyChicago Firecharacterexcept for Boden. Unfortunately, during the season 3 premiere, viewers learned that Leslie Shay had died, which didn’t make for the perfect ending to Boden and Donna’s wedding story.
6Casey & Dawson
Chicago Fire Season 5, Episode 8
Matt Casey and Gabby Dawson were the “it” coupleduring the early years of theOne Chicagofranchise. So, their wedding was certainly a celebration for the characters and viewers alike. It took place in a courtroom like Halstead and Upton’s, but unlike theChicago PDcouple, Casey and Dawson were surrounded by theirChicago Firefriends and family. It was a happy occasion, but it’s a bit tainted knowing how Casey and Dawson’s story ultimately ended.
5Cruz & Chloe
Chicago Fire Season 8, Episode 19
Joe Cruz went througha lotinChicago Fireseason 8. He had just lost his best friend (Otis), and no one could blame him for feeling a certain type of way. On the other hand, one of the best days of Cruz’s life happened in season 8. He married the love of his life, Chloe Allen, in a beautiful ceremony surrounded by their loved ones. Otis’s absence and presence were greatly felt, making Cruz and Chloe’s big dayone of the most beautiful weddings in theOne Chicagouniverse (despite Cruz’s stitches over his left eye).
4Casey & Brett
Chicago Fire Season 12, Episode 6
After Casey andDawson’s breakup inChicago Fire, he got himself involved in a slow-burn romance with Sylvie Brett. Both were hesitant to give in to their feelings, seeing as they didn’t want to hurt Dawson’s feelings. Nevertheless, Casey and Brett eventually couldn’t push down their attraction towards one another, and the two started dating in season 10. Their relationship was short-lived, though, when Casey moved to Oregon.
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Dick Wolf and Matt Olmstead
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In spite of the distance between them, Casey and Brett never stopped loving each other. So, atthe end ofChicago Fireseason 11, Casey returned to Chicago and proposed to Brett, and she said, “Yes.” The couple got married a few episodes into season 12, and the ceremony was beautiful. It was held in an aquarium, and Boden officiated, of course.It was the ideal end to Casey and Brett’s story as they rode off into the sunset together(to Oregon) after their wedding.
3April & Ethan
Chicago Med Season 8, Episode 9
The relationship between Ethan Choi andApril Sexton inChicago Medwas quite a rollercoaster, similar to many otherOne Chicagoromances. However, all of their past strife doesn’t matter because of how flawless their wedding was. April and Ethan got back together during the season 8 premiere, and just nine episodes later, they got married. Their nuptials were beautiful andserved as the perfect way to write out Ethan’s characteras he and April got the happy ending they had always deserved.
