Simple VPS, Windows 2k3, Hosted in Chicago, And Cheap
LIke the title says, requirements are only that it is hosted in Chicago, runs Windows 2k3 so I can log in from the remote control app in windows, and preferably under $30/mo. I only need about 10/15 gigs a month bandwidth max, and HD space, no more than 2 gigs.
Your budget is good enough for a Windows VPS in Chicago. I'd suggest you to go through the VPS offers section. You'll find number of VPS hosting providers over there select few of them, select the search option to find out quick reviews or else post the company names here in the same thread to get fresh feedbacks.
While I do like Nerios I believe their lowest end windows VPS costs $47/mo, though they do run specials in the offers forums so check that out.
Like others have said you can catch good deals on the offers section if you can wait for one. Based on reviews I'm waiting for ServerComplete to have another one of their $15 sales (just missed out on the last one).
Also if you can live with a VPS outside of the Chicago area you'll have more options. Good luck!