The general answer to the question is no. Although I've not stayed at all of the hotels you mention, I've not found a noticeable increase in service, amenities, or upgrades, nor a noticeable decrease in those things with Chicago hotels. As noted, the hotels in Chicago are generally older, so I don't find them as "nice" as those in other cities, but the overall mix of service is comparable to what you would find anywhere.

You also listed several HPs, and you just won't see a ton of differentiation for Globalists there (outside a few pleasant surprises here or there).