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I left a few comments on Reitveld, mainly about the documentation and API design.
However I understand Rolf specifically wanted chunked encoding to work with the existing urlopen() framework, at least after constructing a separate opener object. I think that should be practical with the existing HTTPConnection implementation. Here is some pseudocode of how I might write a urlopen() handler class, and an encoder class that should be usable for both clients and servers:
class ChunkedHandler(...):
 def http_request(...):
 # Like AbstractHTTPHandler, but don’t force Content-Length
 
 def default_open(...):
 # Like AbstractHTTPHandler, but instead of calling h.request():
 encoder = ChunkedEncoder(h.send)
 h.putrequest(req.get_method(), req.selector)
 for item in headers:
 h.putheader(*item)
 h.putheader("Transfer-Encoding", encoder.encoding)
 h.endheaders()
 shutil.copyfileobj(req.data, writer)
 encoder.close()
class ChunkedEncoder(io.BufferedIOBase):
 # Hook output() up to either http.client.HTTPConnection.send()
 # or http.server.BaseHTTPRequestHandler.wfile.write()
 
 encoding = "chunked"
 
 def write(self, b):
 self.output("{:X}\r\n".format(len(b)).encode("ascii"))
 self.output(b)
 self.output(b"\r\n")
 
 def close(self):
 self.output(b"0\r\n\r\n")