15 Best One Chicago Relationships, Ranked

Wolf Entertainment’s One Chicago franchise, which runs on NBC and consists of Chicago Fire, Chicago P.D., and Chicago Med, is known for big emotions, powerful moments, and cliffhangers that leave audiences on the edge of their seats. The franchise launched with Chicago Fire, which follows the firefighters and paramedics of Chicago’s Firehouse 51, and spun off into Chicago P.D., which is centered around CPD’s Intelligence unit. Chicago Med, which spends time with the doctors and nurses at Gaffney Chicago Medical Center, came a few seasons later.

The three shows in the One Chicago franchise have become fan favorites, and they dominate Wednesday night television. What audiences love the most is the way the shows connect with each other, and One Chicago has set the standard for well-done franchise crossovers. Each of the three shows puts time and effort into building the relationships on the show, and the franchise excels at building beautiful stories of friendship, family, and love.

15. Connor Rhodes Found Love with Robin Charles on Chicago Med

Important Episodes for the Relationship

Robin Charles (Mekia Cox) and Connor Rhodes (Colin Donnell) meet for the first time when they order the same drink at the coffee cart, and he almost takes hers in Season 2, Episode 7, “Inherent Bias.” Their flirtation moves to a relationship by the end of the season, which is when things start to get more complicated. Robin begins exhibiting bizarre symptoms in Season 2, Episode 19, “Ctrl Alt,” including hearing rats, losing her ability to focus, and fluctuating emotions. Through the end of Season 2 and into Season 3, Connor and Robin navigate her mental and physical health together, though it certainly takes a toll on both of them. Eventually, in Season 3, Episode 6, “Ties that Bind,” after she is caught shoplifting from the Dolan Rhodes Department Store, which belongs to Connor’s family, Robin decides to leave Chicago without telling Connor so that she can recover on her own.

Though short-lived, their relationship left a mark on Chicago Med fans, who next saw Connor with the woman who ended up murdering his father. Connor was an important part of getting Robin the help she needed, and for most of their relationship, they appeared to be a comfort to one another. Fans had hoped Robin would get better instead of leaving or even come back for Connor, but alas, it was not meant to be.

14. Daniel Charles and Caroline Charles Got Married Again on Chicago Med

Important Episodes for the Relationship

Caroline “CeCe” Charles (Paula Newsome) and Daniel Charles (Oliver Platt) were married once before and had their daughter, Robin, before divorcing. Though their marriage ended, they clearly retained some love for each other, which returns when CeCe comes back to Chicago for additional treatment for her lymphoma. After finally admitting their feelings to each other, they get remarried in Season 4, Episode 22, “With a Brave Heart.”

In Season 5, Episode 9, “I Can’t Imagine the Future,” CeCe’s health begins to seriously deteriorate. Daniel helps her throw a farewell party before CeCe dies. Their relationship is a fan favorite because of how happy they make each other, even when they’re driving each other a little nuts. It’s a beautiful example of giving love a second chance, whether you have a lot of time together or just a little.

13. Paramedics Evan Hawkins and Violet Mikami Fell in Love on Chicago Fire

Important Episodes for the Relationship

Evan Hawkins (Jimmy Nicholas) and Violet Mikami (Hanako Greensmith) met after Evan became the new paramedic chief. Initially, Violet was not a fan of Evan’s, but their relationship changed when he rode along with Violet while Brett was in Portland. Though they tried to keep their distance from one another, they couldn’t fight their feelings and ended up together. Emma Jacobs (Caitlin Carver), a paramedic who tried to blackmail Evan into replacing Violet with her at 51, made things difficult for them for a while, but by the beginning of Season 11, they were happy. Evan was transferred to a different district, which meant they could finally be public about their relationship. Unfortunately, their happiness was cut short.

In Season 11, Episode 3, “Completely Shattered,” Evan rushed to aid a man who had fallen outside a building that was on fire. Evan was still trying to get him away from the building when it collapsed. Violet’s desperate attempt to revive him and her distraught wailing when she realized he was gone were heartbreaking for fans to watch. Their relationship, a sort of enemies to lovers, was fun to watch as it built, which made Evan’s death all the more difficult for fans. Violet continued to deal with her grief throughout Seasons 11 and 12 of Chicago Fire, making the character seem even more real and someone that characters and audiences alike can identify with.

12. On Chicago Med, Dennis Washington Opens Sharon Goodwin’s Heart Again

Important Episodes for the Relationship

Sharon Goodwin (S. Epatha Merkerson) is the Executive Director of Patient and Medical Services at Gaffney Chicago Medical Center, and fans have long wanted to see her fall in love. Goodwin’s husband and the father of her children, Bert (Gregory Alan Williams), ended their marriage in Season 1, Episode 18, “Timing,” and she has been single since — at least as far as fans and her colleagues knew. In Season 9, Episode 3, “What Happens in the Dark Always Comes to Light,” audiences learn that Goodwin has been secretly dating Dennis Washington (John Earl Jelks), the head of Oncology at Med, and they’re finally ready to start telling people.

What makes their relationship so compelling isn’t just that Goodwin is finally dating again but that Washington is helping her see love differently. Throughout Season 9, Goodwin is also dealing with the news that Bert has been experiencing memory issues. Goodwin is there to support her children and Bert as he deals with an Alzheimer’s diagnosis, but she doesn’t leave much room for someone to be there for her. Washington makes a point of showing up when she needs him and reminding her that she can come to him, even if it’s to talk about Bert. Their relationship is a beautiful look at a second chance at love while also showing viewers the importance of letting people into their lives.

11. Wallace Boden Finds His Perfect Match in Teacher Donna Robbins on Chicago Fire

Important Episodes for the Relationship

When Wallace Boden (Eamonn Walker), then Chief of Battalion 25, met Donna Robbins (Melissa Ponzio) in Season 2, Episode 12, “Out With a Bang,” it was at a fire in her apartment building. Boden eventually asks Donna out on a date but abruptly ends things in Season 2, Episode 15, “Keep Your Mouth Shut,” because he felt that he was too damaged and was going to screw up the relationship. In Season 2, Episode 19, “A Heavy Weight,” Donna comes to the fire station to tell Boden important news — she is carrying his child. Though he initially botches the proposal, in Season 2, Episode 21, “One More Shot,” he proposes on the front steps of her school in full dress uniform, and she says yes. They marry in front of Firehouse 51 in Season 2, Episode 22, “Real Never Waits.”

Donna and Boden’s son, Terrance, is born in the back of the Squad 3 truck on the way to the hospital in Season 3, Episode 10, “Santa Bites,” and Wallace’s father comes to stay with them in Season 3, Episode 12, “Three Bells,” much to Donna’s chagrin. Their relationship is tested several times throughout the show, but they stand by each other’s side no matter what. Their relationship is one of the strongest on Chicago Fire and a steady example for Boden’s firefighters of true love.

10. Hannah Asher is Smitten with New Doctor Mitch Ripley on Chicago Med

Important Episodes for the Relationship

New to Med, Mitch Ripley (Luke Mitchell) caught the eye of Hannah Asher (Jessy Schram) pretty quickly, even if she pretended he didn’t. They dance around admitting their feelings for much of the season until they finally nearly kiss in Season 9, Episode 8, “A Penny for Your Thoughts, Dollar for Your Dreams.” Though things continue to move slowly for them, they finally kiss for the first time in Season 9, Episode 12, “Get By With a Little Help From My Friends.”

Their relationship, still in its infancy when Season 9 wrapped, is bound to get more complicated in Season 10. At the end of Season 9, Episode 13, “I Think I Know You, but Do I Really,” Pavel, the man who had been suing Ripley for malpractice, came into the hospital with severe injuries from being beaten and accused Ripley of attacking him. Instead of responding to the accusation, Ripley walks out of the hospital, leaving Asher confused. Fans have loved their relationship because it’s a bit of a redemption for Asher, who previously ended her relationship with Will Halstead because of her addiction, plus Asher and Ripley have both dealt with mental health issues in the past, which made them seem perfect for each other.

9. On Chicago Med, April Sexton and Ethan Choi Complemented Each Other

Episodes Important for the Relationship

April Sexton (Yaya DaCosta), one of Med’s best nurses, and Ethan Choi (Brian Tee), Med’s former Chief of Emergency Medicine, were colleagues first, then friends, before Ethan finally admitted to April that he was interested. They kiss for the first time in Season 2, Episode 23, “Love Hurts,” and from then on, they have a somewhat tumultuous relationship.

While April and Ethan end their relationship after April kisses Crockett Marcel (Dominic Rains), and then April leaves Med at the end of Season 6 to become a Nurse Practitioner, they end up getting back together in Season 8 and ultimately get married. Their relationship is one that fans enjoyed because they challenged each other and made each other better, and when they left Med in Season 8, Episode 9, “This Could Be the Start of Something New,” it was to run a community outreach program for medicine, which felt like the perfect place for them to end up together.

8. Jay Halstead and Hailey Upton Fall in Love and Fall Apart on Chicago P.D.

Important Episodes for the Relationship

When Hailey Upton (Tracy Spiridakos) joined the Intelligence unit at the end of Season 4, she initially began dating Adam Ruzek (Patrick John Flueger). Their relationship didn’t last long, especially once Hailey got partnered up with Jay Halstead (Jesse Lee Soffer). The closer Hailey and Jay got as partners, the stronger their love for each other got — even if it did take them nearly three years to admit it.

Once Hailey and Jay finally admitted their feelings for one another, things moved pretty fast. They share their first kiss in Season 8, Episode 3, “Tender Age,” and by the finale — Season 8, Episode 16, “The Other Side” — they were talking about marriage. Fans loved watching them get together, which made it particularly devastating when it was announced that Jesse Lee Soffer would be leaving in the beginning of Season 10. Chicago P.D. did a great job of building a storyline for Hailey after Jay’s departure, where she started to spin out of control, but that didn’t make the landing from their abrupt ending any softer.

7. On Chicago Fire, Sylvie Brett and Matt Casey Were Meant to Be

Important Episodes for the Relationship

When Sylvie Brett (Kara Killmer) arrived at Firehouse 51 in Season 3, Episode 1, “Always,” Matt Casey (Jesse Spencer) had just asked Gabriela Dawson (Monica Raymund) to marry him. While Matt did end up married to Gabi for a while, after their divorce and her departure from Chicago, it became clear that there was something happening between Matt and Sylvie.

It took them both time to admit their feelings, and their relationship had at least one false start, but eventually, Matt and Sylvie started a serious relationship. When Matt moved to Portland to take care of the children of one of his best friends, who died in Chicago Fire‘s Season 1, Episode 1, “Pilot,” they even tried long distance. They broke up briefly, but neither of them could really move on, and Matt finally asked Sylvie to marry him in Season 11, Episode 22, “Red Waterfall.” Fans rooted for them from the moment it was clear that feelings were developing, so it was a joy to see them get hitched in Season 12, Episode 6, “Port in the Storm,” even if it was Killmer’s final episode. It might have taken them time, but when you know, you know.

6. Christopher and Cindy Herrmann are Chicago Fire’s Mom and Dad

Important Episodes for the Relationship

One of the strongest and most beloved relationships on Chicago Fire is that of Christopher Herrmann (David Eigenberg) and Cindy Herrmann (Robyn Coffin). High school sweethearts Christopher and Cindy have five children — Lee Henry, Luke, Max, Annabelle, and Kenny, who was born in Season 1, Episode 24, “A Hell of a Ride.” Their marriage has stood the test of time because Christopher and Cindy work hard to be a team. When one of them needs the other, they’re always there.

Christopher and Cindy have been through a number of tough moments, including when Christopher was stabbed in Season 4, Episode 10, “The Beating Heart,” and later, in Season 11, Episode 11, “A Guy I Used to Know,” when Cindy is diagnosed with cancer, but they have come through them stronger than ever. The other firefighters often turn to Christopher and Cindy for advice about marriage and children, and fans have loved seeing their relationship on the show because of how much their love for one another jumps off the screen. If Christopher Herrmann is the beating heart of Firehouse 51, then his marriage to Cindy is the beating heart of all One Chicago relationships.