Reinstall openssl:

brew reinstall openssl

And then:

export DYLD_LIBRARY_PATH=/usr/local/opt/openssl/lib:$DYLD_LIBRARY_PATH

Or create the link manually:

cd /usr/local/lib
sudo ln -s /usr/local/opt/openssl/lib/libssl.dylib libssl.dylib
sudo ln -s /usr/local/opt/openssl/lib/libcrypto.dylib libcrypto.dylib

Reinstall python:

brew reinstall python

Upgrade pip packages:

pip install -U --user $(pip freeze | awk -F'[=]' '{print $1}')