19. Under new direction, Chicago Fashion Week (pictured) promises excitement, and the Art Institute’s Fashion Design School makes Chicago a prime fashion destination. Magnificent Mile is the place to find the latest styles. The Mile houses one of just two Paul Stuart menswear shops in the nation. Optimo, on the South Side, is one of the last traditional men's hatters. Boutiques Maria Pinto and Ikram feature First Lady Michelle Obama’s favourite designers. Stay on trend with the city’s Chicago Collection magazine. Next . . .