Only you know what you need. All I can do is share my opinion and perhaps give you a new insight. For new laptops costing less than $250, I would pick the laptop which syncs with the office services you primarily use.
If using Microsoft Office 365, a cheap Windows laptop would work nicely and don't expect it to run Premiere or the latest games at 24-100 fps. Think of it as an office machine with basic web browsing ability. Miscellaneous applications such as DropBox or Norton would work nicely on it.
If using Google services such as Gmail, Drive, or Docs, go with the Chromebook. While it is true that the Windows laptop could still use Google services, one would be even more productive on the Chromebook. It is mainly a browser with some off-line capabilities which includes playing movies from Google Play. You'd spend less time updating the OS or applications. Chromebook does the browsing tasks well and stays out of the way like a tablet.