Lori Healey

If all had gone according to plan, Healey would be scrambling right now to get Chicago in tiptop shape to host the Summer Olympics. Instead, as head of McPier since April, she’s scrambling to keep tourists and conventioneers coming to the city. The headwinds are strong, including $3.5 billion in bond debt, flat hotel occupancy, and trade show cancellations. The recent spike in shootings isn’t exactly selling the Windy City as a vacation hot spot, either. But Healey is a tough, seasoned politico. She’s betting on a new McPier hotel, DePaul arena, and Navy Pier makeover to lure visitors.