changing window surface area/sqrft in Energy plus chicago office building IDF

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FenestrationSurface:Detailed does have a multiplier field that could be used to increase or decrease the effective window area, but as mentioned in the EnergyPlus documentation for FenestrationSurface:Detailed this should be done with caution, depending on the scenario itmay produce odd results, warnings, or simulation errors, this isn't a very large model, so changing the geometry by hand instead should also be very easy, unless this is a test for something larger.

Direct IDF

You could use Eppy for example to manipulate the IDF file. You could loop on each Fenestration object, and do your own routine to scale the window with a given factor: what I've successfully done in the past it to resize windows around their centroid (you'll need to calculate that), see the implementation in openstudio-standards for an idea of the code.

That being said, if I recall correctly, this prototype building only has perfectly rectangle windows, so scaling them should be a ton easier than that, you could just raise / lower the sill height.

OpenStudio

What I would probably do instead would actually be to generate this DOE prototype building using OpenStudio and the BCL Measure Create DOE Prototype Building, then you could just apply for example this other BCL measure resize_existing_windows_to_match_a_given_wwr that does the resizing of the windows around their centroid for you.

Note: In both cases, mind that if your goal is to reduce the WWR, then you will be fine raising the sill height or resizing around the centroid. If your goal is to greatly increase the WWR, you're at risk of creating a window that is larger than its base surface, in which case you could perhaps instead use Set Window to Wall Ratio by Facade