Gold Upgrades at Chicago Hilton Properties

Hi Everyone,

I am looking to stay at a Hilton property in Chicago this weekend. I am Gold with them.

From you guys past experience, which properties do you get upgraded to Executive floor the most? This includes DoubleTree etc.

I am looking into the Hilton Palmer House hotel since I've stayed with them before. The opening rates are at $71/night for one double bed. What are my chances of getting upgraded to the Executive Floor?

Should I spend a extra $40 to secure an executive floor room?

Thanks!