Chicago voters will decide on a proposal to increase real estate taxes to fund homeless programs, sparking debates about the downtown's recovery, migrant influx, and trust in progressive leaders. The measure aims to generate at least $100 million annually, with varied opinions on its potential impact. Supporters view it as a chance to address homelessness, while opponents fear negative repercussions on the real estate market. The vote reflects a shift in Chicago's political landscape, with both sides actively mobilizing voters for the upcoming election.