Interesting review! That suite is impressive. I don't think I've ever gotten an upgrade there as a Bonvoy Titanium.
I stayed at the JW Chicago last month after not visiting Chicago since Covid and had some of the same opinions as you. It was the most empty I had ever seen that hotel, by far, but Chicago in general seemed "lower occupancy" with less traffic, fewer pedestrians, some closed stores and restaurants, etc. The front desk agent who checked me in gave me some blowback for using the state government rate, asked to see my state government ID, which I showed her, and then she told me that the hotel policies were changing and I would not be able to obtain that rate again in the future. I was surprised, because it looked like a strange time to be turning away future business, given the "ghost town" feeling there. She did honor the rate for this stay. I had stayed there 4-5 times previously, and I was shocked how different it was -- far less busy than it used to be. On the up side, the Executive Lounge evening food presentation was very nice, and the whole Executive Lounge staff was really friendly and helpful. I also enjoyed the gym and the Italian restaurant upstairs. But if I can't get the state government rate there again, I'll find a new choice in Chicago.