The One Chicago franchise, with its interconnected world of firefighters, police officers, and doctors, has given us some of the most dramatic and emotional moments in television history. But few events have been as anticipated and talked about as a wedding. When a major character finally walks down the aisle, it’s not just a ceremony; it’s the culmination of years of on-screen drama, heartbreak, and resilience. Every wedding is a narrative landmark, a payoff for the fans who have invested so much in these characters’ love stories.
But not all weddings are created equal. Some were grand, romantic affairs that brought us to tears. Others were quiet, rushed moments that left us wanting more. From City Hall to a country chapel, here is a definitive ranking of every major One Chicago wedding, from worst to best, based on emotional impact, narrative importance, and overall execution.
6. Matthew Casey & Gabby Dawson
Where It Happened: The courthouse.
The Context: This wedding, which should have been a monumental moment for one of the show’s core pairings, felt like a footnote. Casey and Dawson got married in a quick, last-minute courthouse ceremony as part of a desperate, and ultimately failed, attempt to become foster parents. There were no friends, no family (save for a couple of witnesses), and no traditional vows. It was a plot device more than a celebration of love. For a couple that had been through so much, from the intense push-and-pull of their early relationship to multiple breakups and a near-death experience, this rushed wedding was a massive disappointment. It lacked the emotional weight and grandeur that their tumultuous, long-running love story deserved, leaving a bitter taste in the mouths of fans who had rooted for them for years.
5. April Sexton & Ethan Choi
Where It Happened: The hospital chapel.
The Context: The relationship between April Sexton and Dr. Ethan Choi on “Chicago Med” was a rollercoaster of on-and-off drama. After a long-running, complicated history, the couple got married in a quiet, low-key ceremony in the hospital chapel. While it was a sweet moment that gave their characters a happy ending, it felt a little rushed and convenient. The wedding served as a way to write them off the show as they moved to a new city to run a mobile clinic. While it was emotionally satisfying to see them finally commit to each other, the wedding itself wasn’t an epic event. It was a nice, tidy conclusion, but not a monumental one.
4. Wallace Boden & Donna Robbins
Where It Happened: The firehouse.
The Context: This wedding was the first major celebration in the heart of Firehouse 51. After a tumultuous relationship that was nearly derailed by a vindictive ex, Chief Boden and Donna Robbins finally tied the knot in an impromptu ceremony right inside their beloved firehouse. The wedding was a beautiful, heartwarming affair that showed the entire crew coming together to support their leader. It was a charming, simple ceremony that perfectly reflected the stable, grounded nature of Boden and Donna’s relationship. While it didn’t have the high drama of some of the other weddings, its execution was perfect. It felt organic, and it solidified the idea that the firehouse was more than just a workplace—it was a family.
3. Randall “Mouch” McHolland & Trudy Platt
Where It Happened: A beautiful, traditional church.
The Context: The wedding of Mouch and Trudy Platt on “Chicago Fire” was a perfect blend of unexpected humor and genuine, heartfelt love. Their relationship, a quirky mix of Mouch’s timidness and Trudy’s fierce, no-nonsense attitude, was one of the most charming in the entire franchise. The wedding itself was a beautiful, traditional ceremony that brought the entire Firehouse 51 family and the Intelligence Unit together. It was a moment of pure joy and happiness, a rare feel-good event in a show that often deals with tragedy. The sight of the famously tough Trudy in a wedding dress, looking genuinely happy and vulnerable, was an emotional payoff. This wedding ranks high not for its drama, but for its honesty and its ability to make the audience feel the love that they shared.
2. Kim Burgess & Adam Ruzek
Where It Happened: A courthouse.
The Context: This might surprise you, given its location, but the wedding of Kim Burgess and Adam Ruzek on “Chicago P.D.” was a top-tier event because of its profound emotional weight. This wasn’t a City Hall marriage of convenience; it was the long-awaited culmination of over a decade of will-they-won’t-they drama, heartbreak, failed engagements, a shared child, and unimaginable trauma. The wedding was a private, intimate ceremony attended by only their closest family. It was exactly what their story needed: a quiet, peaceful moment of commitment after years of public chaos. The wedding felt completely and utterly earned. It was a testament to their resilience and their unwavering love for each other, and for long-time fans who had waited through years of pain for this moment, it was the perfect payoff. It was a beautiful and fitting end to one of the most complex love stories in the One Chicago universe.
1. Sylvie Brett & Matthew Casey
Where It Happened: The firehouse.
The Context: This was arguably the most highly anticipated wedding in the history of the entire franchise, and it lived up to every expectation. The love story between Sylvie Brett and Matthew Casey was a slow-burn, years in the making, complicated by their shared history with Gabby Dawson and their own insecurities. Their wedding was a perfect event. It was held in the very firehouse where their love story began, and it brought back a fan-favorite character for a beautiful farewell. Every detail was perfect, from the emotional reunions to the heartfelt vows. The wedding was a celebration of love, second chances, and the idea that two people who were meant to be together could finally find their way back to each other. It was a grand, emotional, and narratively significant event that gave both characters the happy ending they deserved. It was a tear-jerking, beautiful moment that will be remembered as the pinnacle of the One Chicago weddings.
Honorable Mention: Hailey Upton & Jay Halstead
The Context: While not a traditional ceremony, the courthouse wedding of Hailey Upton and Jay Halstead deserves a special mention. It was a simple, no-frills moment that was a perfect reflection of their intense, no-nonsense personalities. It wasn’t a fairy tale, but it was honest and true to their characters, a perfect example of their commitment to each other.
In the end, every One Chicago wedding is a unique reflection of the couple at its center. They are not just ceremonies; they are the narrative punctuation marks on years of hard-fought love. They remind us that even in a world of high-stakes rescues, tragic losses, and constant danger, love is the one force that can bring true peace.
