Chicago truly is the best city. Sure I am a little biased being a native but there is so much history, culture, and architecture that makes this city so rich. One of first and wealthiest neighborhoods was the Gold Coast. I have rented many apartments at 1350 N Lake Shore Drive, which prior to 1950 was home to the first and largest private residence of it's time, the Palmer mansion. Their mentality to live on the lakefront started a movement and society followed.
As lake Michigan began eroding away the shoreline the city simply extended itself back eastward in landfill. What followed was a beautiful bullevarded street to connect Oak Street to North Ave; which soon stretched all the way north becoming one of the nation's first superhighways.