The university provided vpn client.

Available for Mac, Windows, and Linux

• Install Instructions (MacOS)

If you click through the installer it seems to fail, but you can still install the package via the command line.

% sudo arch -x86_64 installer -pkg "/Volumes/AnyConnect VPN 4.9.05042/anyconnect-macos-4.9.05042-core-vpn-webdeploy-k9.pkg" -target /
Password:
installer: Package name is AnyConnect Secure Mobility Client
installer: Installing at base path /
installer: The install was successful.

• Install Instructions (Windows 10)

There is client available for download when you access https://cvpn.uchicago.edu.

You are on your own as per usual. The steps are very similar to the other OS's.

You might find it is easier to use SSH port forwarding . Though, in some cases the Cisco AnyConnect client might be required.