Tucked into a 1926 co-op in Chicago, this three-bedroom, 18,000-square-foot apartment first charmed Devin Kirk, VP of Merchandising at Jayson Home, when he saw it on TV. As Jennifer Aniston and Vince Vaughn fought over the enviable space in the 2006 rom-com "The Break-Up," the designer marveled at its barrel-vaulted entryway, high ceilings, and great proportions. Fourteen years later, Kirk, his husband, Chad, and their five-year-old son, Harry, moved into the space. Read more here: http://hsbu.u