No doubt the winds were the issue. ORD had winds of 5-15mph all night, as did other metro OBS sites, which kept temps from dropping much. As you said, with no CAA associated with the winds, there was nothing to significantly drop the temp.
Out west, the wind situation was much better...though there were still issues. You would see temps drop quickly with calm winds, only to have winds kick up to 5mph and temps rise...with that progression having occurred for a while at many OBS sites.
There was just enough gradient on the northeast side of the ridge, preventing winds from totally going calm out west, and be much lower in to metro...which would have lead to much colder temps everywhere with perfect radiational cooling conditions. Probably would have seen sites like SQI/RPJ/FEP/ARR/DPA end up near -40.