Just finished my first trip to Chicago. Flew in on Saturday morning and left Tuesday morning.
Stayed at 3 hotels:
Night 1 - Palmer House (booked King business class - chose standby upgrade $10 to Executive Level, no upgrade. Perfect location for seeing the museums and a performance at Symphony Center)
Night 2 - LondonHouse (upgraded to higher floor)
Night 3 - Waldorf Astoria (Points stay, upgraded a couple days before check in from Superior King to Grand Deluxe King W/Fireplace and Terrace - facing North)
With the rates I was able to get, if I were paying for a 3 night stay at 1, I would have chosen LondonHouse (points Waldorf).
I enjoyed aspects of each, but overall LondonHouse hit the most notes. Although the rooms are not as large, the room was large enough for everything I needed (I would take river view + rooftop, over terrace to be honest).
I had originally booked a regular king room two months in advance (with points). Around 3 weeks in advance, I checked again and noticed that rates had dropped, so I switched my booking to cash and upgraded to a Vista Room (rather than chance an upgrade).
Using online check in I selected a room on the 13th floor. At check in I was updated to the 18th floor (both room would have been in the newer portion of the building with floor to ceiling windows). No problem with the room being dark (would be interested in seeing some of the rooms with river/lake views, although smaller windows).
I was given a voucher for free continental breakfast. There was no mention of the $18 credit, but the breakfast included Scrambled eggs, sausage links, and bacon (this was a $6 upcharge at Palmer House). I was at breakfast around 7AM and there were only 2 other hotel guests, so no problems with servers, just had to leave my voucher on the table. After breakfast I got a cup of coffee to go and used this as an opportunity to have the rooftop to myself (it had rained most of the weekend, so not much opportunity for night pictures/drinks).
Only minor complaint:
Water pressure in shower (same as Palmer House, Waldorf was better).
Definitely would consider coming back, although there are more hotels I want to check out (the Wit, Drake, Chicago Athletic Assoc, the Alise).