This neighborhood has run the full spectrum during the past century. In the late 1800's until the Great Depression, Uptown as known as an expensive playground for those could afford the area. Mainly, the inhabitants were people living in downtown Chicago who would spend their weekends relaxing by the Lake or shopping in one of the many ritzy department stores that operated here.
Some of the nicest mansions in the city are located in Uptown. In the sub-neighborhood known as Buena Park (running from Irving Park Road to Montrose and Lake Michigan to Broadway Avenue) there are several larger than life homes built back in the turn of the (20th) century that are guaranteed to impress. The boundaries of Uptown include: Irving Park Road to the south, Broadway Avenue to the west, Foster Avenue to the north and Lake Michigan to the east.
Over the years since then, the area has gone from one of wealth, to one primarily filled with low-income rental property and boarding houses, to once again an area that has a lot going for it. It's location next to the Lake, it's variety of well-built housing stock now being rehabbed, and the ever-convenient "el" all make this neighborhood more and more of a draw.
Uptown is no stranger to music and entertainment. There are no less than three large performance halls that are still standing today - all within a few blocks of one another. The Uptown Theater, able to hold almost 4500 people, was at one time the second largest movie theater in the United States, and is considered a historical landmark in Chicago. The Riviera Theater continues to bring in some fairly big names in rock n' roll. The Aragon Ballroom, built originally as a large dance hall, has brought in such big name entertainers as Frank Sinatra decades ago to the Rolling Stones as recently in the recent past.