I have been using cygwin for a while. To say the least, I get to do X11 forwarding on windows. Windows 10 now has an experimental feature called Bash for Windows. I think this was released along with the Windows 10 Anniversary update. However, I have not succeeded in getting X11 to run on it.

This post is about how to install pip for python on cygwin. Cygwin does not have a package that provides pip as Ubuntu does. But getting pip on Cygwin is really easy. This answer on Stack Overflow outlines the process.

python -m ensurepip

Then do the same for python 3

python3 -m ensurepip

Now, upgrade pip to the latest version.

pip install --upgarede pip

The problem with this is that it makes pip2 the default pip and you loose access to pip3. I got around this by -

python3 -m pip install --upgrade pip

Phew !!! I can finally install youtube-dl without hassles -

pip3 install youtube-dl