Similarly, I live in Silicon Valley and the San Francisco Bay Area. Both are represented as place=region nodes. The former is located in front of a historically significant building, and the latter is smack-dab in the middle of the bay for neutrality. A node doesn’t express the scale of the region, but it’s an admission that we aren’t in the business of defining arbitrary boundaries. We take the same approach for continents as well as many cities’ neighborhoods.
I’d support replacing the Chicago metropolitan area boundary relation with a place=region node named Chicagoland, representing only that informal place, nothing more scientific than that. It could be centered near the Loop right alongside the Chicago node, or anything else that comes to mind. I split out a Chicagoland (Q134718040) item on Wikidata that we can link to.