Is painting from a photograph and then selling the painting illegal?

No.

That is unless someone owns the photograph or the subject. Say for example if it was a photo from a professional photographer or maybe a photo of a owned (copyright) image.
 
No it is not. As long as it's not in anyway a photocopied painting as in, you looked at the photo and then painted in, not you scanned in the photo printed out a guide and then painted it.
 
That question came up during the last presidential election with the Obama 'Hope' poster:

http://news-briefs.ew.com/2011/01/12/lawsuit-obama-hope-poster/
http://artsbeat.blogs.nytimes.com/2009/10/16/ap-says-shepard-fairey-lied-about-hope-poster/
 
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