Not to get philosophical, but it’s been decreed. Gladstone Park is one of 228 vaguely-defined secondary communities allowed to exist in the City of Chicago with no commonly-recognized borders. Just because the community thinks it should be so.
Anyone trying to research Gladstone Park will find there is little history — especially early history — written specifically about it. There is not even an entry for the community in the Chicago Historical Society’s Electronic Encyclopedia of Chicago, the standard for all that’s relevant to the city’s roots. And the online Wikipedia, which’ll publish anything and everything, has a mere three short paragraphs on Gladstone Park and only under the subheading for Jefferson Park.
They say whatever doesn’t kill you will make you stronger. In Gladstone Park that whatever is its streets. They are the one element that shaped this Far Northwestern Chicago neighborhood more than any other.
It is difficult to trace all the subdivisions proposed for and built in Gladstone Park without physical access to old building plans from Chicago’s Department of Planning and Development. However, we can get some idea of how the community’s residential areas grew by examining advertisements placed in area newspapers by developers hoping to attract first-time homeowners eager to buy lots and ready-built dwellings.