12. Natalie & Will
Chicago Med – Season 4, Episode 9
Natalie Manning and Will Halstead’s wedding was cut short when Will had to enter protective custody. Their relationship was always turbulent, and just as they were about to tie the knot, danger struck. Luckily, in Season 8, they reconnected, and Will moved to Seattle to be with Natalie.
11. Maggie & Ben
Chicago Med – Season 5, Episode 17
A sweet but forgettable wedding that took place in a bowling alley. Though it was heartwarming to see Maggie happy, the couple eventually divorced in Season 9, which brings this wedding down in the rankings.
10. Charles & CeCe
Chicago Med – Season 4, Episode 22
Dr. Daniel Charles and CeCe’s Hawaiian-themed wedding was touching, but also bittersweet, knowing CeCe was terminally ill. She passed away in Season 5, casting a shadow over their heartfelt ceremony.
9. Halstead & Upton
Chicago PD – Season 9, Episode 9
Jay Halstead and Hailey Upton had a low-key courthouse wedding with no guests. While they are a beloved couple, the lack of ceremony and their eventual breakup in Season 10 make this wedding feel underwhelming.
8. Burgess & Ruzek
Chicago PD – Season 12, Episode 22
After years of on-again, off-again tension, Kim Burgess and Adam Ruzek finally got married. Unfortunately, we barely saw the ceremony, and it lacked emotional payoff despite the couple’s long history.
7. Boden & Donna
Chicago Fire – Season 2, Episode 22
Chief Boden and Donna had a stable, loving relationship, and their firehouse wedding was nearly perfect—until tragedy struck. The episode ended with an explosion, and in the next season, it was revealed that Leslie Shay had died, marring the joy of their big day.
6. Casey & Dawson
Chicago Fire – Season 5, Episode 8
The courtroom wedding of Matt Casey and Gabby Dawson was warm and surrounded by friends. However, the happiness was short-lived as their relationship eventually ended, making the wedding feel bittersweet.
5. Cruz & Chloe
Chicago Fire – Season 8, Episode 19
Despite recent loss, Joe Cruz married Chloe Allen in a heartfelt ceremony. Otis’s absence was felt deeply, but his spirit lingered in the love surrounding the event. A beautiful wedding, marked by both joy and remembrance.
4. Casey & Brett
Chicago Fire – Season 12, Episode 6
After much hesitation, Matt Casey and Sylvie Brett confessed their love. Their aquarium wedding, officiated by Boden, was stunning and served as a fitting send-off as
3. April & Ethan
Chicago Med – Season 8, Episode 9
Ethan Choi and April Sexton’s wedding was elegant and meaningful. After years of ups and downs, they got back together and married just nine episodes later—an ideal exit for Ethan’s character and a perfect resolution for their love story.
2. Mouch & Trudy
Chicago Fire – Season 4, Episode 18
The only cross-show marriage in the franchise. Mouch and Trudy’s quirky romance culminated in a heartfelt ceremony at Molly’s with friends from both Chicago Fire and Chicago PD in attendance. Memorable, funny, and sincere.
1. Severide & Kidd
Chicago Fire – Season 10, Episode 22
The ultimate One Chicago wedding. Stella Kidd and Kelly Severide said “I do” aboard a boat, with vows so sweet they were unforgettable. Their bond, forged through fire and hardship, makes them the definitive couple of Firehouse 51.
