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Yeah, you've been doing great work on Chicagoland—I was inclined to just let it languish in its old miserable state before you started cleaning it up ;)
I think we may have been talking past each other on the Lake Co. issue—I also basically just want it cross referenced from both Chicagoland and Northern Indiana, not described here in detail. That and links to the principal Chicago suburbs there would be useful. Since they should just be links + one liner blurbs, there shouldn't be any worry, I think, about keeping things maintained across multiple pages.
If you just deleted all the hotel listings, then that probably wasn't the way to go. It would be better to create outline articles for the various cities/towns where they are located and then copy-paste them in under the respective sleep sections. Ideally, though, you are right that a region article shouldn't have sleep listings. There are exceptions, like if there are isolated B&Bs way off in the countryside, but those are not going to be found in Chicagoland! Those hotel listings can still be accessed through the page history, though, so it's no big deal.
My only one big recommendation for the article is that we use more prose—more travel writing. So some pleasantly written paragraphs rather than a purely functional bulleted list for entries under the see, do, eat, sleep, etc. sections would be ideal, while still maintaining the links to the most important destinations. What you've already done, though, is still way better than what we had before. I'd also recommend dropping the county divisions within each section, since there are many, and moving towards a more fluid description of what's available (linking the cities, followed by ", county"?). I'd also pare down the counties section to something more like a quick list of the relevant counties (example). Prose description of the area can be pared down to one paragraph introduction in the counties section, I think. More detailed information about the counties should go into county articles, although we can wait to create those and let the info sit in Chicagoland for now.