Chicago

Perhaps the most quintessentially 'American' of cities, Chicago offers world-class culture with a warm Midwestern attitude. From the working-class South Side to the trendy hipster havens in the North, Chicago offers up everything you could ask for in a city. From Grant Park, the skyline is awe-inspiring. Serious shoppers head straight to the boutiques and multi-level malls of the "Magnificent Mile" while sports fans flock to Wrigley Field to watch the beloved Cubs. Take a rattling El ride through Chicago's downtown Loop and bring the city's booming business district up close and personal.