Hi all -
I thought I'd post an update now that we have finally shipped our wine from Chicago to Los Gatos in case anyone needs resources in the future. We used Domaine, though I also had a good dialogue with Joel at Western Carriers (thanks Wine doc!). Really, the decision between the two was just the ease of using Domaine (driven by their shipping hub locations in relation to our Chicago storage and home in the Bay) and I have no doubt Western would have done just as well by us.
We packed our own wine so that we could do an inventory (suffice it to say that my father is an impulse buyer with zero organizational skills). Many thing were in wooden crates, which were fine with Domaine. For any loose bottles or partial cases, we used cardboard boxes with cardboard dividers (no styro shippers). The folks at Domaine Chicago put everything on a pallet that was then wrapped in black plastic, so no one could see the contents, and kept it in a climate controlled area until it was picked up by refrigerated truck. The whole process from drop-off at Domaine to my cellar took just over two weeks (one week at Domaine waiting for the truck pick-up, and one week of transit).
All in all, a fairly straightforward process and a good group of people to work with. Their team was communicative and responsive, helped us load/unload wine, and didn't even roll their eyes when I checked every box (all 50 of them) before signing off on the shipment in CA.
And now we just get to enjoy the wine!