Alderman Robert Maldanado is vacating his seat in the 26th Ward and Alderman Ariel Reboyras is retiring after nearly two decades in the 30th Ward.
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Candidates vying to replace them took part in a forum Friday.
Four acres of vacant land known as the Belmont Triangle is up for sale. It sits in the 30th Ward.
Residents say the future of this area, bordered by Belmont, Pulaski and Milwaukee, is pivotal in choosing their next alderman.
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"What happens there is really the tipping point, are going to create space for current residents to stay," said 30th Ward resident, Juliette DeJesus Alejandro.
Stopping gentrification and providing more affordable housing for current residents is a big issue in the race to replace longtime Alderman Ariel Reboyras.
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"We need to elect someone who understands how gentrification tears up our communities," said 30th Ward aldermanic candidate Jessica Gutierrez.
Guitterez is running for a 2nd time. Four years ago, the daughter of former Congressman Luis Gutierrez, forced Reboyras in a runoff and lost by under 100 votes.
Guitterez and two of her competitors participated in a candidates forum Friday.
"I'm the only candidate in the 30th Ward with the experience in municipal government that is not tied to the old political machine," said fellow 30th Ward aldermanic candidate Juan Pablo Prieto.
"Our community is not being listened to by the people of power," added 30th Ward aldermanic candidate Warren Williams.
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Similar to the 30th Ward, for sale signs and empty lots prime for redevelopment are scattered around the nearby 26th Ward on the city's Northwest Side.
Residents say longtime Latino families are being forced out due to rising property taxes.
"We are tired of promises, we are not here to ask we are demanding because we want change," said 26th Ward resident Monica Espinoza.
Because Angee Gonzalez Rodriguez did not show up to the forum, 26th Ward residents only heard from one candidate -- Jesse Fuentes. She is endorsed by retiring Alderman Maldonado.
"I'm the only candidate in this race that has committed to not taking any campaign contributions from multi-million dollar developers," Fuentes said.
Aldermanic races are kicking into high gear with early voting starting in all 50 Wards on Monday. Half of Chicago voters usually vote before Election Day, either by early voting or vote by mail.