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The building, according to the Chicago Urban League, is one of the most significant donations in its history and will help bolster its entrepreneurship and workforce development training.
As Chicago dealt with a shortage of shelter beds, Toronto was also managing a shelter crisis amid an increase in people seeking refuge in Canada.
Canada is known for its friendlier approach to immigration, but it also faces hurdles as record numbers of people are displaced globally.
Plans to add housing in the downtown corridor will help reinvigorate the district, architects and developers said, but there are still construction challenges with turning office spaces into residential units.