Chicago - Always the Palmer House Hilton
Location was great... convenient to everthing - 
Fantastic decor and a classic vibe make this a great place to stay. The grand lounge is an amazing space... it's a great place to sit, have a drink, relax and people watch. There seemed to be somthing going on there every afternoon and evening - a bustling place.
The room we stayed in had two beds and two full baths - very historic feel. Baths were both upgraded and very nice. 
I'd recommend this to any traveler that likes that old school feel... but with all the modern facilities.