Dionne and Jamada are in the market for the charm and quality a vintage Chicago home can offer. Dionne's love for vintage started with her love for thrift shops, while Jamada's passion and respect for vintage is a result of being a professional carpenter. While Dionne loves the feminine details and 'doll house' look of Victorians, Jamada wants something more masculine and sturdy looking like a Tudor. But with a $250,000 budget, will they find the perfect vintage home that satisfies both of their needs? Or will their dreams be whisked away in the bluster of the Windy City?