Republican Gubernatorial Candidate Darren Bailey Moves Into Chicago Apartment

Bailey hopes to connect with city voters after past criticism of Chicago as a 'hellhole'

Apr. 16, 2026 at 12:38am

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A serene, cinematic painting depicting a lone figure standing in the window of a dimly lit apartment, the warm glow of the setting sun casting long shadows across the room, conveying a sense of solitude and contemplation.As a Republican gubernatorial candidate seeks to connect with urban voters, his move to a Chicago apartment raises questions about the authenticity of his campaign outreach.Chicago Today

Darren Bailey, the Republican nominee for Illinois governor, has moved into an apartment on Chicago's near South Side that will serve as a campaign headquarters for his Chicago-area operations. Bailey, a former state lawmaker and farmer from downstate, has previously been critical of Chicago but now says he wants to focus more on getting to know voters in the city and suburbs.

Why it matters

Bailey's move to Chicago represents an effort to appeal to urban and suburban voters after his previous gubernatorial campaign in 2018, when he received only about 15% of the vote in the city. As the Republican nominee, Bailey will need to find a way to connect with a diverse range of Illinois voters to have a chance at defeating the incumbent Democratic governor, JB Pritzker.

The details

Bailey said this year's move is part of his promise to focus more on getting to know voters in the city and suburbs, after previously calling Chicago a 'hellhole.' However, he insists he hasn't forgotten about his downstate base that propelled him to the party's nomination. Bailey said he hopes a donor will help cover the apartment's cost, which can range around $2,000 per month in the South Loop neighborhood.

  • Bailey lived in the John Hancock Center on Michigan Avenue four years ago with a similar goal, though it didn't pay off as he lost the race by 12 percentage points to Gov. JB Pritzker.
  • Bailey secured the Republican nomination for governor last month.

The players

Darren Bailey

The Republican nominee for Illinois governor, who is a former state lawmaker and farmer from downstate Clay County.

JB Pritzker

The incumbent Democratic governor of Illinois, who defeated Bailey by 12 percentage points in the 2018 gubernatorial election.

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What they’re saying

“Darren Bailey has spent his entire career demonizing Chicago and the people who live here. He can change his address, but that doesn't change the facts. Darren Bailey is the same extreme, unsuccessful, and totally unqualified candidate he's always been. When Illinois voters reject Donald Trump's lapdog for the third time this fall, hopefully he gets the message.”

— Alex Gough, Pritzker campaign spokesperson

“I've always said that when I see something wrong, I'll call it out, and I believe I always have, so I felt the necessity to say this is not right what happened here, and I believe an apology would go a long way in rectifying this.”

— Darren Bailey

What’s next

Bailey's move to Chicago will be closely watched as he attempts to connect with urban and suburban voters ahead of the November election against the incumbent Governor Pritzker.

The takeaway

Bailey's decision to move into a Chicago apartment represents a strategic shift in his campaign approach, as he tries to overcome his past criticism of the city and appeal to a broader range of Illinois voters. However, the Pritzker campaign has already dismissed the move as an empty gesture, arguing that Bailey's core views on Chicago have not changed.