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What Happened to Hailey Upton on Chicago P.D.?

The cop played by Tracy Spiridakos was a force of nature within the 21st District and Chi-Hards adored her.

By Jessica White

It takes some serious grit and determination to thrive within Chicago P.D.'s Intelligence Unit and, when Hailey Upton (Tracy Spiridakos) was on the case, suspects were always checking over their shoulders.

How to Watch

Watch Chicago P.D. on NBC and Peacock.

Upton was one of the most passionate investigators to grace the 21st District, coming to Chicago P.D. in Season 4 and spearheading dozens of grueling investigations. (She also made several guest appearances on Chicago Fire and Chicago Med, and even made her way to Dick Wolf's FBI franchise.)

Upton broadened the definition of what it meant to be an exemplary cop, and Chi-Hards relished watching her relationships around the precinct — particularly her complicated connection with her former partner-turned-ex-husband, Jay Halstead (Jesse Lee Soffer).

Hailey Upton on Chicago P.D Episode 421

When did Hailey Upton first appear on Chicago P.D.?

Chicago P.D. fans first met Upton in Season 4, Episode 21 (“Fagin”), after she collaborated with the Intelligence Unit as a detective for CPD's Robbery-Homicide Unit. Upton was irritated that Intelligence had swooped in on her case but, after combining brains with Sergeant Hank Voight (Jason Beghe) and Halstead, she learned she worked well with the investigators.

By the episode's end, Voight had offered Upton a job within his unit, which she accepted in the following episode ("Army of One"). 

Upton was determined to prove herself within the CPD, often becoming the first officer to throw herself into a case or prioritize an investigation over her personal life. Upton's policing style was defined by empathy and calculated vulnerability — she was privy to spinning stories to coax confessions but always makes room for survivor testimony — and her tumultuous childhood strengthened her skill in identifying abuse risk factors, which paved the way for dozens of arrests.

Her toxic upbringing also meant Upton had spent significant time at the CPD as a young girl, which is how she first met the tough-as-nails Trudy Platt (Amy Morton). Spending time with Trudy eventually inspired Upton to become a cop — and, while typically stoic, Trudy couldn't help but get emotional after meeting Upton as an adult and witnessing how far she'd come.

Chicago Pd 1113 Hailey Upton2

When did Hailey Upton leave Chicago P.D.?

Upton resigned from the Intelligence Unit in the Season 11 finale ("More").

After the unit caught wind of a horrific serial killer on the prowl in the Windy City — and Voight landed in the killer's clutches — Upton found and saved her commander, though not without sustaining injuries. 

After recovering, she had a chat with Voight about why she became a cop but now wanted a change.

"I'm pretty sure I've just been remaking my childhood every day making myself the victor," Upton admitted. "I don't want that to be true. I don't want to still be affected by my childhood, to be an adult stuck in some cage she made."

"What do you want?" Voight asked.

"I just want to feel better, be better, you know?" Upton confessed. "Start over, I guess?"

Upton's ultimate fate was a bit of a cliffhanger: after perusing job listings for the FBI, she packed up her apartment and jumped in a cab headed for O'Hare. When the cab driver asked her where she was traveling, the episode faded to black.

Halstead and Upton on Chicago P.D Episode 501

What happened between Hailey Upton and Jay Halstead on Chicago P.D.?

From Seasons 5 to Season 7 of Chicago P.D., Upton and Halstead were partners and had a platonic friendship, but their relationship shifted at the end of Season 7.

After Halstead was shot in Season 7, Episode 10 ("Mercy), Upton refused to leave his side at the hospital and finally admitted she loved him as a partner, the first sign of her deeper feelings. (Halstead was, of course, equally devoted to Upton.)

RELATED: A Look Back at Halstead and Upton's Slow-Burn Romance on Chicago P.D.

In Season 8 of Chicago P.D., she received a job offer from the feds in New York City, and was forced to consider her future both in Chicago and with Halstead. 

In Season 8, Episode 3 ("Tender Age"), Upton told Halstead she wasn't taking the job because she belonged in Chicago with him. After she admitted that it had been a long time since she'd viewed him as "just her partner," the two kissed for the first time. The couple's relationship quickly blossomed, and while they kept it professional on the job, Voight eventually learned of their relationship after the couple shared their first "I love you"s. 

In the Season 8 finale  — after accidentally killing a suspect involved in the kidnapping of her colleague Kim Burgess (Marina Squerciati) — she proposed to Halstead, telling him she always wanted him in her life. He was blindsided.

When did Hailey Upton and Jay Halstead get married on Chicago P.D.?

In the Season 9 premiere ("Closure"), Halstead eventually asked Upton why she proposed, and she admitted that she craved stability and trusted she'd always be happy with Halstead at the end of their respective stressful days. 

RELATED: These Are The Most Beloved Couples on Chicago Fire, Med, and P.D.

Halstead then surprised Upton by asking her to marry him, admitting that he'd known for years that they were meant to be together.

The pair moved in together in Season 9, Episode 3 ("The One Next to Me") and broke the news of their engagement to the rest of the Intelligence Unit shortly after.

Halstead eventually decided that he wanted to get married as soon as possible, and the two eloped for a confidential courthouse wedding in Season 9, Episode 9 ("A Way Out").

Halstead and Upton on Chicago P.D Episode 909

Why did Hailey Upton and Jay Halstead divorce on Chicago P.D.?

Halstead resigned from the police department in Season 10, Episode 3 ("The Great Man") and accepted a job with the U.S. military to hunt down drug cartels in Bolivia. He left Chicago — and his wife — with just a day's notice.

"It's not forever, it's eight months, maybe a little longer," Halstead told Upton before leaving. "But I swear to you that we're gonna get through this because you're the love of my life, and if I'm yours, then you'll know that you have to let me go."

RELATED: Jesse Lee Soffer Finally Reveals Why He Left Chicago P.D.

Upton was heartbroken but chose to support her husband, even though the job prevented him from calling or texting her. After she called Halstead's boss in Season 10, Episode 12 ("I Can Let You Go"), Upton learned that her husband had extended his tour in Bolivia without notifying her. 

Her anger toward Halstead reached a fever pitch in Season 10, Episode 20 ("Fight") after Upton survived a horrific kidnapping but was forced to confront the fact that her husband would never have noticed her missing because he wasn't there.

After tearfully gazing at pictures and keepsakes in the couple's home, Upton took off her wedding ring. 

RELATED: Are Upton and Halstead Actually Divorced? Showrunner Gwen Sigan Explains That Premiere

By the Season 11 premiere ("Unpacking"), Upton and Halstead were officially divorced. Picking up six months after Season 10's events, Halstead was gone for a full year before Upton ultimately signed and sent the divorce papers.

Hailey Upton on Chicago P.D Episode 1012

What happened between Hailey Upton and Adam Ruzek on Chicago P.D.?

Upton had a brief fling with Intelligence Unit Detective Adam Ruzek (Patrick John Flueger) in Season 6, Episode 6 ("Bad Boys"), after Halstead was shot.

Halstead recovered, but Ruzek was there for Upton during the fallout. After the pair woke up together after a one-night stand, they began exploring their feelings but agreed to keep their relationship on the down-low. Considering they were surrounded by Intelligence officers, the jig was up fairly quickly. 

RELATED: What to Know About Burgess and Ruzek's Chicago P.D. Romance

Their colleagues' knowledge of the once-secret romantic relationship escalated some of the issues already present within the couple's interactions on the job. Upton fundamentally disagreed with Ruzek's policing style and aggression issues, while their status as coworkers consistently chipped away at their relationship.

The two broke up in Season 6, Episode 12 ("Sacrifice"), but Ruzek was keen to comment that their ending was more complicated than simple workplace drama — implying that she harbored feelings for Halstead while he still carried a torch for Burgess.

Ruzek and Upton ultimately worked better together as friends and have remained close since.

 

When did Hailey Upton leave Chicago P.D. and appear on FBI?

In Season 7 of Chicago P.D. Upton orchestrated the death of a man who had murdered one of her valued informants, and Voight sent her to New York City's FBI office for a few weeks to fill in for an undercover agent.

She appeared on Dick Wolf's FBI in Season 2, Episode 19. ("Emotional Rescue") where, surrounded by straight-laced investigators, Upton quickly learned dirty policing is never the route to a clean arrest.

She returned to the Windy City during the Chicago P.D. Season 8 premiere ("Fighting Ghosts"). 

Hank Voight and Hailey Upton in Chicago P.D. Season 11 Episode 11

Watch Chicago P.D. on NBC and Peacock.

Originally published Jan 17, 2024.