“There was an error checking the latest version of pip” error occurs in Python when there are “bugs in the pip module while installing the module.” The message is simply informing you that pip couldn’t check for its latest version due to network issues or because internet access is disabled (as is the case in this environment).
How to fix it?
To fix the “There was an error checking the latest version of pip” error, “update Pip manually using this command.”
python -m pip install --upgrade pip # Or python3 -m pip install --upgrade pip
There’s also a chance that Pip’s dependencies may be causing problems. To ensure everything’s up to date, you can update setuptools and wheel using these commands once you’ve updated Pip.
pip install –upgrade wheel pip install –upgrade setuptools