1 - 20 of 2,640 Works in Hailey Upton
Navigation
Listing Works
-
Tags
Summary
Detective Rebecca Small transfers to Chicago Intelligence after a covert narcotics operation in Miami leaves her with a scar she refuses to talk about and ghosts she can’t quite outrun.
Chicago is supposed to be a fresh start.
New city.
New unit.
New rules.Instead, Rebecca finds herself buried in the brutal rhythm of Intelligence: violent cases, long nights, undercover assignments, and a team that slowly starts to feel dangerous in its own way.
Safe.Especially Detective Dante Torres, the one person patient enough to see through the armour she built after Miami.
But some ghosts don’t stay buried.
As old trauma resurfaces and whispers from Miami begin bleeding into Chicago’s criminal underworld, Rebecca is forced to confront the terrifying truth:
the most dangerous part of undercover work was never accidentally falling in love with Javier Navarro.It was that some part of her still might.
- Language:
- English
- Words:
- 112,599
- Chapters:
- 38/?
- Hits:
- 120
-
Tags
-
Tags
Summary
“We’ve been asked to assist on a case that Intelligence caught this morning.”
Hailey’s mind freezes for a second, but she tries to maintain her composure and not make it look too obvious. Intelligence… Jay. This is not how she thought today was going to go.
“Seems like a strange request. We don’t usually work any cases with Intelligence,” She states. She’s trying her best to sound indifferent, but her mind is running a mile a minute trying to figure out how this might work.
“Yeah, unfortunately this has come from the higher ups. They've asked me to send over two officers to the 21st district this morning to work alongside them in this case. High profile too.”
Hailey takes another sip of her coffee to give her some time to organise her thoughts. Two officers, he said. It didn't have to mean her.
--------------------------------------
Jay Halstead is a detective in the Intelligence division. The team are called to a case where they end up working alongside Robbery homicide. Hailey Upton is a detective in Robbery Homicide. Working together on the case means that the lines between personal and professional begin to blur. Can they work together to help solve the case?
-
Tags
Summary
Hailey hasn’t seen Jay in 3 years since the day he left Chicago, her, for Bolivia. After a catastrophic case involving a plane mysteriously going dark that lead Jay, working for the military and Hailey now as a special agent working with the FBI down the same path hoping to take down the same drug cartel, she invites him for a drink at the bar opening the door again to endless possibilities.
A post crossover fan fiction -
CHICAGO'S LAST STAND: THE ORIGIN STORY by mediocrefanficwriter
Fandoms: Chicago Fire (TV), Chicago Med (TV), Chicago PD (TV)
02 Jun 2026
Tags
Summary
‘A zombie apocalypse happens dramatically in films and novels. In February CDC advised all citizens to stay indoors.’
Over 2 million people once called Chicago home, people the CPD swore to protect. People who lived in communities the CFD pledged to selflessly serve. People whose lives Chicago Med worked overtime to save. Together there was nothing Chicago couldn't survive, until now. Now the world is up in flames and life as they know it is over. Leaving your everyday heroes grasping at strands of their humanity.
‘Chicago’s Last Stand: The Origin Story’ follows multiple characters. It’s a horrifying twist of story-lines all connected to create a truly unique read. If you’re looking for the typical self insert book this isn’t for you. Nobody's safe from zombies, not even your favorite character(s).
-
Tags
Summary
Finding himself upset with how his afternoon had gone racing on the streets of Chicago, Alex Bowman decides to have a couple of drinks to forget about what had happened.
With having just finished up one of the tougher cases she'd been through, and recently having her heart broken by a fellow detective in her unit, Hailey Upton decides to head over to Molly's for a couple drinks to wish away everything she was feeling.
Hailey knew going to Molly's there was a risk running into that very detective, but yet perhaps she finds someone else who will touch her heart instead.
-
Tags
Summary
The final piece for now in the series. Bex is left at Med, will she find the stability she needs?
Series
- Part 3 of Healing is an art
- Language:
- English
- Words:
- 5,948
- Chapters:
- 8/8
- Hits:
- 10
-
Tags
Summary
Jay and Hailey share a drink, a hotel room, and the kind of night that reminds them some things are never really over.
AKA Post-crossover reunion fic
-
Tags
Summary
A story inspired by one of my childhood favourites. Jay and Hailey are transported to an alternate universe full of fencing, fighting, torture, revenge, giants, monsters, chases, escapes, true love, miracles… doesn’t sound too bad, right?
-
Tags
Summary
(after reckoning 13x13) When a case brings them back to Chicago, Jay and Hailey see each other again for the first time. With the aim to end the day at a bar, neither of them suspects that this night will connect them forever (including all consequences)....
-
Tags
Summary
A story about what happened in Bolivia and where Jay's search for a way out of the gray areas took him.
-
Tags
Summary
Nothing will break Sylvie and Matt
-
Tags
Summary
Landscapes had always been his favourite thing to photograph, that was until she walked into his frame and his whole world got turned upside down in the space of two weeks. Now the only thing he wanted to photograph was her, if only so he had something to remember her by when their inevitable goodbye came.
-
Still Us by tatgrl
Fandoms: Chicago PD (TV), Chicago Med, Law & Order: SVU, FBI (TV 2018), FBI: International (TV 2021)
30 May 2026
Tags
Summary
What really made Jay Halstead walk away from Chicago—from his badge, his team, his wife?
Was the Army his answer… or just another escape? Did he really go straight to Bolivia? Or was there a detour? And what if Erin Lindsay ever crossed his path again?This is a Linstead story about love lost, love found, and the long road in between. A deep dive into messy minds, old wounds, and unfinished business. An emotional journey of soul-searching, rebuilding, and the kind of connection you never really let go of.
Not just a fic. A fix-it. A healing process. An escape.
Check out the one-shots in the series as well: past memories, missing scenes… and keep an eye out for future glimpses coming soon.
Series
- Part 1 of Still Us
-
Tags
Summary
No one tells you that the fog of war doesn’t end when the war is over. For Jay there was one thing that kept him afloat, her voice was his lifeline, she was his lifeline, and she didn’t even know it.
Upstead AU -
Tags
Summary
This is a continuation of my previous work. Bex’s story takes a turn as she faces another hospital stay at Chicago Med with the help of Hailey, Jay, and the rest of the Chicago crew will she finally be safe?
Series
- Part 2 of Healing is an art
-
We're Coming to the Cottage by Hollstead81
Fandoms: Chicago Fire, Chicago PD (TV), Heated Rivalry (TV)
26 May 2026
Tags
Summary
Firehouse 51 and District 21 are granted a much needed break and head to Ontario, Canada for their week-long lakeside vacation.
While at a café, Lizzie Novak reconnects with an old college friend, Hayden Pike, who unexpectedly recruits the crew to be players in a charity hockey match for the Irina Foundation that Hayden was in charge of organizing.
Over the course of the next week chaos ensues, life-long friendships are formed, and what the Chicagoans and Canadians thought would be a relaxing week turned into an unforgettable experience.
-
Tags
Summary
Hank thought he was content with his the direction his life was going, until the day his unit answered a robbery call.
Jenna knew her life needed to change, and Chicago seemed like the perfect place for a new beginning.
Voight/OC with a side of Linstead.
Series
- Part 1 of Sweet Home Chicago
-
Tags
Summary
Jay’s falling deeper and deeper with Voight and Hailey doesn’t know what to do anymore. He’s never there, she never sees him, he’s not the man she married.
Jay doesn’t realise how bad things have got until Hailey ends up in hospital, but is it already too late? Will he be able to come back from this? Will he step up when she needs him most?
-
Dusk Till Dawn by Howlingwolf27
Fandoms: Chicago PD (TV), Chicago Fire, Chicago Med, 9-1-1 (TV)
22 May 2026
Tags
Summary
When Jay disobeyed orders to stay away from the guy that killed his dad and got shot Hank is angry.
Jay faces the consequences of his decision and he also deals with an angry brother as well.