7Summer Sun for You Forever There's no one that makes him happier - truly - so when her smile begins to fade, he knows he has to put his own emotions aside in the moment to help her through what might be the darkest moment of her life. Upstead.
Chicago PD, T, English, Romance & Angst, words: 2k+, favs: 14, follows: 18, 1/24, J. Halstead, H. Upton
686 We Are » Jay and Hailey are ready to take the path toward expanding their family one more time, but are they ready for the other paths that come up along the way? Sequel to We Can. Upstead future fic.
Chicago PD, T, English, Family & Hurt/Comfort, chapters: 63, words: 273k+, favs: 137, follows: 155, updated: 1/2 published: 1/4/2021, J. Halstead, H. Upton
8 Believing is Seeing Jay and Hailey's daughter is old enough to start understanding more Christmas traditions, so Vanessa convinces Hailey to buy her an Elf on the Shelf. They expected the elf to bring their daughter a lot of joy, but they didn't expect her to bring them the best gift of all. Upstead Oneshot.
Chicago PD, K+, English, Family & Romance, words: 5k+, favs: 21, follows: 8, 12/19/2021, J. Halstead, H. Upton
8 Tis the Damn Season Christmas shouldn't be about avoiding your mother, but when Hailey tries to do just that, Jay gives her the strength to do the opposite. What neither of them was necessarily expecting, though, was that he'd get the strength to do something he'd been wanting to do for a while as well. Upstead S7 oneshot.
Chicago PD, K+, English, Friendship & Romance, words: 7k+, favs: 21, follows: 13, 12/13/2021, J. Halstead, H. Upton
15 All Too Well Jay hasn't seen Hailey excited about much in months, so when she's finally smiling on her own, he aims to understand why in hopes that he can keep her this happy forever. Upstead Engaged Oneshot.
Chicago PD, K+, English, Romance, words: 3k+, favs: 14, follows: 4, 11/19/2021, [H. Upton, J. Halstead]
3 A Dwindling Mercurial High Hailey is fine. At least, that's what she keeps saying because right now, Jay's not fine - they can't both be not fine. She needs to be strong enough for the two of them despite how close she is to crumbling right there and then. Upstead Post 9x03 Oneshot.
Chicago PD, K+, English, Hurt/Comfort & Romance, words: 1k+, favs: 20, follows: 10, 10/30/2021, [J. Halstead, H. Upton] K. Burgess
12 A Flash of a Home Jay and Hailey want the perfect apartment to move into together, but the perfect apartment isn't a balcony or large kitchen; rather, the perfect apartment is one they can grow together and love each other endlessly in. Upstead oneshot.
Chicago PD, K+, English, Romance, words: 3k+, favs: 26, follows: 8, 10/26/2021, J. Halstead, H. Upton
4 Fall into Me Hailey didn't realize how heavy she was feeling until Jay willingly took some of the weight from her. Post 9x04 Upstead oneshot.
Chicago PD, K+, English, Angst & Romance, words: 2k+, favs: 24, follows: 14, 10/18/2021, J. Halstead, H. Upton
1 Survive Hailey finds herself next to the Chicago river in the middle of the night and all she can do is scream. She's trapped and has no place to go. She just needs to let out all of her frustration and anger - the cold night in the middle of the city seems like the perfect time and place to do so.
Chicago PD, T, English, Angst, words: 969, favs: 12, follows: 6, 10/12/2021
21I'd Do It With You » Hailey and Jay grew up debating if they'd have kids when they're older, but it's not until they're dating each other that the debate stops and becomes a real conversation between two people. Upstead.
Chicago PD, K+, English, Family & Hurt/Comfort, chapters: 3, words: 15k+, favs: 31, follows: 26, updated: 10/11/2021 published: 9/20/2021, [J. Halstead, H. Upton]
7 Closer to Heaven, Closer to You Hailey freed herself from her father when she was 20, but it isn't until ten years later with Jay that she feels like she's really ready for a better future. Upstead friendship and dating oneshot. Or Hailey has a secret tattoo and the only one she tells its story to is Jay.
Chicago PD, T, English, Hurt/Comfort & Romance, words: 5k+, favs: 34, follows: 10, 10/2/2021, [H. Upton, J. Halstead]
4 Silent Promise Kim's experiencing unimaginable pain, and yet she tells Hailey that she wants to talk to Jay. He's not sure why, but he knows that he does want to help her because it's Kim and she deserves that much. 7x13 Oneshot.
Chicago PD, K, English, Angst & Friendship, words: 1k+, favs: 23, follows: 15, 9/13/2021, J. Halstead, K. Burgess
8 It's Different Now Hailey had to spend thirty-three days away from Jay while in New York. She was supposed to change while there - Voight's orders - but when she steps off the airplane back in Chicago, she realized that more changed than just her. Upstead Season 7 Oneshot.
Chicago PD, K, English, Friendship, words: 1k+, favs: 27, follows: 12, 9/12/2021, [H. Upton, J. Halstead]
10 The Cure to Nightmares Just when Hailey's own nightmares came to a stop, she realized that Jay was still experiencing his own. She's not quite sure how to help him, but when a case falls into their lap and they meet a dog, she learns that maybe there is a cure for nightmares after all. Dating Upstead Oneshot.
Chicago PD, K+, English, Romance & Hurt/Comfort, words: 5k+, favs: 27, follows: 8, 9/8/2021, [H. Upton, J. Halstead]
129 Cruel Summer » Upstead AU: Detective Hailey Upton isn't looking for a committed relationship, but when Jay Halstead slips into her life and shows her that life isn't always cruel, she has to decide if she's going to follow him where she'd never gone or stay where she feels safest.
Chicago PD, T, English, Romance & Hurt/Comfort, chapters: 13, words: 48k+, favs: 67, follows: 78, updated: 8/26/2021 published: 7/12/2021, J. Halstead, H. Upton
9 Kiss Me on the Sidewalk Jay and Hailey go for a walk every Sunday morning, and almost every time that it rains while they're on the walk, Jay makes sure to kiss Hailey because it's his favorite "couple thing" to do. Upstead Dating/Married Oneshot. Upstead Week!
Chicago PD, K+, English, Romance & Family, words: 3k+, favs: 26, follows: 7, 7/25/2021, J. Halstead, H. Upton
4 Not What I Expected When Hailey tells the story of how she and Jay came to live together, she always starts by saying "It wasn't what I expected" because really what girl thinks she'll ask her boyfriend to move into her apartment when they're sitting on his bathroom floor with his hand bleeding between them? Dating Upstead Oneshot. Upstead Week!
Chicago PD, K+, English, Romance & Humor, words: 2k+, favs: 23, follows: 4, 7/24/2021, J. Halstead, H. Upton
6 Not a Cursed Word Hailey's watching Kim, Makayla, and Adam and realizes she's not quite sure she knows what home means until Jay describes to her his home and it clicks that maybe home isn't a place, but a feeling. Dating Upstead Oneshot. Upstead Week!
Chicago PD, K+, English, Romance, words: 1k+, favs: 23, follows: 9, 7/23/2021, J. Halstead, H. Upton
4 An Anniversary Kiss After a disappointing ending to an intense case, Jay tries cheering up Hailey with breakfast in bed for an anniversary he may or may not have made up the night before. Dating Upstead Oneshot. Upstead Week!
Chicago PD, K+, English, Romance, words: 2k+, favs: 18, follows: 4, 7/22/2021, J. Halstead, H. Upton
2 Dream of Some Epiphany Jay thought he had every inch of Hailey memorized, but when he finds a scar that he's not familiar with, he reminds her that he loves all of her - past and all. Dating Upstead Oneshot. Upstead Week!
Chicago PD, T, English, Romance & Hurt/Comfort, words: 2k+, favs: 31, follows: 6, 7/21/2021, J. Halstead, H. Upton