Last year I finally upgraded my work laptop to a 13″ Macbook Pro. I rarely bring that machine home; when I did, I realized that I couldn’t easily hook it up to my vintage 20″ Apple Cinema Display (matte screens forever!). That monitor uses a DVI connector, which I currently have hooked up to my home machine using a DVI-to-Mini DisplayPort adapter.
The first thing I tried was to daisy-chain that adapter to a Thunderbolt 2-to-Thunderbolt 3 adapter, but my Macbook wouldn’t recognize the monitor.
After reading this helpful thread, what finally worked was: HDMI-to-DVI adapter, connected to a USB-C hub with HDMI input. It’s not pretty, but it works. The USB-C hub happily accepts the pass-through USB from the display’s own USB/Firewire hub (although I’ll always use the USB-C hub’s USB-A ports for better transfer speed).
The adapters I used: