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Chicago PD finale spoilers: Is an Upstead wedding coming in Chicago PD season 9?

Cody Schultz
Cody Schultz

One Chicago Center

CHICAGO P.D. -- "The Other Side" Episode 816 -- Pictured: (l-r) Jesse Lee Soffer as Jay Halstead, Tracy Spiridakos as Hailey -- (Photo by: Lori Allen/NBC)

The Chicago PD season 8 finale proved to be quite the game-changer in more ways than one.

Of course, the two biggest storylines throughout the episode were Burgess’s (Marina Squerciati) fight to survive following her abduction and Voight’s (Jason Beghe) decision to fall back into his old ways of policing in order to get results. Both plotlines should have major implications on season 9 both in terms of the direct fallout for the two characters as well as those around them.

Among those most directly affected by Voight’s actions was Upton (Tracy Spiridakos), who was forced to get her hands dirty due to the decisions Voight made in his efforts to get answers about Burgess’s whereabouts. Following the ordeal, it was clear Upton was deeply affected by the events of the evening which is perhaps we never quite saw the big Upstead proposal coming in the closing moments of the episode — signaling season 9 should be a major season for Upton both professionally and personally.

** Warning: The following post contains spoilers from the Chicago PD season 8 finale **

Does Jay Halstead propose to Hailey Upton on Chicago PD?

While the Chicago PD finale does feature a surprise Upton proposal, it’s Upton who pops the question to Halstead (Jesse Lee Soffer). Upon arriving back at her apartment following the ordeal with Voight and the suspect responsible for shooting Burgess, Upton tells Halstead she loves him before suggesting they take their relationship to the next level in asking him to marry her.

Does Jay Halstead say yes to Hailey Upton’s proposal?

Does Halstead say yes to Upton’s proposal? That’s the question lingering on the minds of Upstead fans and it’s one we’re going to have to wait until Chicago PD season 9 to learn the answer to. This is because the Upstead proposal was part of the finale’s many cliffhangers.

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In terms of the odds of Halstead saying yes? We’d say they’re likely 50/50, as we could truly see things going either way. Halstead could choose to accept Upston’s proposal due to the strong feelings he has for her in recognizing that would be the next reasonable step in their relationship. Or, he’ll assure Upton that he’s not going anywhere and suggest they not rush into marriage on a whim.

Are Jay Halstead and Hailey Upton getting married?

Should Halstead say yes to Upton’s suggestion that they get married, we could very well see the couple getting married in Chicago PD season 9. However, we’ll have to wait to see what Halstead’s reaction to Upston’s proposal will be when the new season begins this fall!

Will Chicago PD season 9 feature an Upstead wedding?

If Halstead and Upton do indeed decide to get married, it seems incredibly likely that the pair will opt for a more simple courthouse wedding than some big extravagant affair. Because of the manner in which Upton proposed to Halstead, it’s possible we could see the pair get married sometime in Chicago PD season 9; however, at this time, there has been no confirmation of whether the pair will exchange I Do’s next season.

For the latest Chicago PD season 8 spoilers and news, plus more on the entire series, follow the Chicago PD category at One Chicago Center.

Cody Schultz

Cody Schultz

Cody Schultz is the Senior Director of Entertainment at FanSided, where he leads editorial strategy across the company's entertainment websites. A trusted voice in the entertainment space with over a decade of experience, Cody has been part of the FanSided team since 2014, covering television and movies. His work spans celebrity interviews, deep-dive features, and event coverage, including reporting from some of the biggest industry events such as San Diego Comic-Con, New York Comic Con, D23 Expo, and the Golden Globe Awards. Cody has been a part of the One Chicago fandom from the first season of Chicago Fire, and has even visited several of the filming locations of the hit series. He has interviewed several members of the casts of Chicago Fire, Chicago Med, and Chicago PD including Jesse Lee Soffer, Christian Stolte, Joe Minoso, David Eigenberg, Steven Weber, Jason Beghe, and Sarah Ramos. When he’s not writing or crafting editorial strategies, Cody is likely watching the latest hit series, geeking out about all things Marvel, or hanging out with his two