In the heart of Chicago, where sirens scream and tensions run high, romance still finds a way. Across the One Chicago universe — Chicago Fire, Chicago P.D., and Chicago Med — love has blossomed, often in the most dramatic of ways. Weddings in these shows are never ordinary; they’re filled with emotion, unpredictability, and, occasionally, disaster. But whether they’re fairytale perfect or a complete train wreck, each one has left a lasting impression. So let’s walk down memory lane and rank the most talked-about weddings — or failed attempts at them — from worst to best, all while celebrating the fiery passion and human vulnerability these characters bring to their vows.
Starting at the bottom of the list is Will Halstead and Natalie Manning from Chicago Med. What should have been a beautiful union turned into a storm of miscommunication and missteps. Will’s involvement with the FBI, coupled with Natalie’s growing doubts, meant their big day never even happened. While their love felt genuine, the wedding-that-wasn’t left fans more frustrated than fulfilled. It wasn’t the lack of a happy ending that hurt — it was the lack of any closure at all. That’s what earns them the unfortunate honor of being ranked the lowest.
One of the most long-awaited pairings in Chicago Fire was Sylvie Brett and Matt Casey. Their relationship had all the elements of great TV: longing, separation, and slow-burning affection. So when they finally decided to tie the knot, fans were thrilled. However, the ceremony itself felt surprisingly underwhelming. While heartfelt, it lacked the emotional grandeur expected after such a long journey. Still, their love felt real, which earns them a solid mid-tier spot.
Hailey Upton and Jay Halstead from Chicago P.D. deserve special mention for doing things differently. Their courthouse wedding was quiet, intimate, and deeply emotional. No pomp, no drama — just two people making a serious commitment. It wasn’t showy, but it felt incredibly real. Sometimes, simplicity is more powerful than spectacle. Their decision to keep things low-key resonated with fans who valued emotional honesty over grandeur.
Connor Rhodes and Robin Charles’s wedding from Chicago Med was a beautiful blend of tradition and tension. Between hospital emergencies and Robin’s complicated relationship with her father, the lead-up was intense, but the payoff was worth it. Their love felt mature, grounded, and ultimately tragic, which added layers to their emotional wedding. It was a moment that felt earned, making it one of the more emotionally rich unions in the franchise.
Narrowly missing the top spot is Kim Burgess and Adam Ruzek from Chicago P.D.. After years of emotional highs and lows, shared trauma, and intense character development, Burzek fans finally got their moment in Season 12. Their wedding wasn’t just a fan-service moment — it was a culmination of years of pain, healing, and deep connection. The emotional payoff, combined with Marina Squerciati and Patrick John Flueger’s standout performances, made this one unforgettable.
Finally, the gold medal goes to Joe Cruz and Chloe Allen from Chicago Fire. Their wedding had everything: emotional build-up, character growth, supportive friends, and genuine joy. Unlike many of the other weddings, theirs felt both meaningful and celebratory. It wasn’t just about saying “I do” — it was about embracing a future filled with love, despite the dangers and unpredictability of their lives as first responders. Their ceremony struck the perfect balance between drama and heart, which is why it sits at the top of our list.
