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I am not a regular in Chicago, but can usually find a decent boutique property when I do stay. However, location is all in Chicago, and the Hilton is pretty central, which is why I guess it can rest on its laurels with unrenovated rooms.
Note you can often ask for a paid upgrade at check in. $20-$30 will often secure a better room, but as I will never darken the HIlton’s door again, I don’t know if they even have better rooms.