Between Chicago Fire, Chicago P.D., and Chicago Med, many episodes from all three of these popular drama shows have left fans sobbing into a blanket. With Chicago Fire being the longest-running of the trio, it's safe to say they have delivered a fair share of heartbreak to their fans.

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Over the last ten years, Chicago Fire has proved that they are not afraid of tearing your heart into a million pieces. They are somewhat professionals at it by now. From the deaths of beloved characters like Leslie Shay (Lauren German) to accurately tackling real-world struggles like coping with a miscarriage, Chicago Fire is one drama show that knows how to hit you where it hurts.

Season 1, Episode 19 — "A Coffin That Small"

casey, severide, mouch and kidd walking in their uniforms in chicago fire

This Season 1 episode had viewers emotional within the first five minutes. A little boy had fallen into a laundry chute while playing with his brother and gotten stuck inside, sadly not surviving his injuries.

Making this even more heartbreaking, the boy's mother stopped by the firehouse to bring them a photo she said her son would've wanted them to have. The picture was of her son dressed up as a firefighter as that's what he wanted to be when he grew up. By the end of the episode, there wasn't a dry eye at the sight of seeing the entirety of Firehouse 51 lining the sidewalk to honor the little boy.

Season 1, Episode 22 — "Leaders Lead"

casey from chicago fire stood next to a flame

Before Gabby (Monica Raymund) and Casey (Jesse Spencer), there was Hallie (Teri Reeves) and Casey, and while Hallie only appeared for one season, it didn't make her death any easier to watch.

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From the anguish radiating from Casey as he begs her to breathe to him breaking down in the doctor's arms when the worst outcome is confirmed, this episode is hard to get through without crying. And when Mills (Charlie Barnett) walked up to them, and Casey just clung to him while the rest of the team stood heartbroken, what little emotional stability you may have had left almost certainly disappeared.

Season 7, Episode 6 — "All The Proof"

Severidefrom chicago fire looking upset

While he wasn't a regular during his run on the show, Benny Severide (Treat Williams) quickly became a notable character. So hearing the news that he'd had a stroke came as a complete shock for both Kelly (Taylor Kinney) and the fans.

Benny sadly died before Kelly could make it to Med to see him. During a chat with Boden (Eamonn Walker), Kelly admitted that the last words he'd said to him were that Boden was a better father than he was. Boden tells him that Benny had helped get the commissioner to back off the firehouse, leaving Kelly shattered. Seeing Kelly break down over his guilt and grief was heartbreaking.

Season 4, Episode 4 — "Your Day Is Coming"

casey from chicago fire with tears in his eyes

This Season 4 episode brought some very emotional scenes. Between Gabby almost dying and the loss of her and Casey's unborn baby, this was jam-packed with moments that had fans reaching for the tissues.

Gabby was rushed in for surgery to save her life, and Will Halstead (Nick Gehlfuss) of Chicago Med, the medical drama of the One Chicago universe, was there to see her through it. From capturing the real pain of losing a child so accurately to seeing Gabby in denial after learning about the baby, this episode was hard to watch without feeling pure heartache for the couple.

Season 5, Episode 10 — "The People We Meet"

dawson and casey together at the firehouse in chicago fire

Following on from the loss of their baby the year before, Casey and Gabby were hit with another blow when they had to say goodbye to Louie, the little boy they'd earned foster rights to at the end of Season 4.

Seeing the couple having to deal with the loss of another child was so upsetting. Given everything they had already been through, saying goodbye to Louie was extremely painful, especially for Gabby, who struggled to cope with the situation they'd found themselves in once again.

Season 3, Episode 1 — "Always"

shay and severide smiling from chicago fire

In the explosive cliffhanger that was the Season 2 finale, the whereabouts and conditions of everyone inside the building were unknown. With Chief Boden outside, unable to reach anybody on the radio, it was unknown if anyone was injured.

Shay took the brunt of the explosion. From Severide performing CPR to Casey, Mouch (Christian Stolte), Herrmann (David Eigenberg), and Cruz (Joe Minoso) forcing him and Gabby out of the way to get her out, the opening five minutes of this episode was enough to have you sobbing for the rest of it. Then, between Gabby's guilt, to the flashbacks thrown in, this episode never stopped waving the heartache around. RIP Leslie Shay.

Season 5, Episode 22 — "My Miracle"

chicago fire 5x22 cruz brett gabby waiting to hear news

"You're my miracle, Gabby." What part of this episode wasn't emotionally destroying? It's hard to say which part of this one hurt the most. Although, the thought of losing Casey, Herrmann, and Mouch all at once was way up there.

The episode ended on what might be the show's cruelest cliffhanger. With most of the team trapped inside a burning warehouse with no exit, Mouch having a heart attack, and Casey breaking everyone's hearts by saying goodbye to Gabby over the radio, this wasn't an easy watch. And it was only made worse by the agonizing four-month wait to find out who'd lived or died!

Season 5, Episode 20 — "Carry Me"

severide and anna from chicago fire walking in the hospital

From Erin Lindsey (Sophia Bush) to Renee Royce (Sarah Shahi), Kelly had a few relationships over the seasons. But, there was nothing quite like the bond between him and Anna Turner (Charlotte Sullivan). Anna may have only been in ten episodes throughout Season 5, but she made a heartbreakingly lasting impact on Severide and the fans.

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From the moment they met, there was something special between them. What started as a donor-recipient relationship turned into a beautiful bond cut way too short. There were so many touching moments between these two in the short time they had together, but in this episode, seeing Kelly break down in her father's arms after she sadly passed away from cancer was soul-crushing.

Season 4, Episode 10 — "The Beating Heart"

herrmann from chicago fire looking rather upset

Christopher Herrmann is the beating heart of the Chicago Fire family. Throughout the last ten years, he's been a counselor, father figure, and shoulder to cry on for everyone in the One Chicago universe. So when Freddy stabbed him midway through Season 4, the thought of losing him was terrifying.

After being rushed to Med, Herrmann suffered from many complications. From going into hypovolemic shock to ultimately being rushed into surgery to try and control the bleeding, his firehouse family came dangerously close to losing him. On top of Herrmann's critical condition, the heartfelt moment between him and Cruz was the icing on the cake to shatter your heart even more.

Season 8, Episode 1 — "Sacred Grounds"

otis and herrmann from chicago fire smiling up at something

It's safe to say that the Season 8 opener held nothing back, bringing one of the most painfully emotional deaths in the One Chicago franchise. It took away a beloved member of Firehouse 51 with a piece of everyone's heart included.

Following the dramatic events of Fire's Season 7 finale, Cruz finds Otis (Yuri Sartarov) badly injured amidst the rubble. Otis woke up at Med and said something to Joe in Russian before he sadly passed away, leaving fans in bits. The episode ended as Boden revealed a memorial dedicated to Otis and translated his last words to Cruz. "Brother, I will be with you, always." When Cruz broke down in front of his memorial and the entire team knelt with him, we were there crying with them.

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