I'm going to say what no one else will. You really should consider priceline/hotwire.

Using sites like Better Bidding you can be reasonably certain of the hotel you'll receive in advance and you can save 50%+. This definitely holds true in Chicago; fantastic deals abound most of the year. It takes a lot of status benefits/points to make up for 50% $ savings.

In general, you could also get good deals with local independent hotels directly. I've even used ski lodge rentals in the off season. Nothing like coming home to an actual condo at night.

When I'm billing through to a client, I have no problem paying market rate at a chain hotel. It's part of our contract. But if you are stuck with the bill, the economics are different.