Looked great online but really undelivered. Old fashioned, in need of updating.
My husband is a Hilton Honours member and we have stayed in several Hilton hotels now for both business and pleasure, including Rome Cavalieri, London Bridge, Paris La Defense, Hilton Malta, Hilton Berlin and Hilton Metropole Brighton. And, as good as Chicago may look online due to the sheer size of it, this was sadly the most disappointing. A real shame as Chicago is such a great city and we expected more.
We were in town to go to the marathon and upon arrival the place is impressive - the entrance is very grand. We were offered an upgrade to a King suite, lake view and whilst very happy at first, we were soon disappointed by how dated and old the interior of our room and indeed the whole floor was. Old brown swirly carpet, a stale smell to the room, old brown furnishings, corny marble lamps, an old bath that was about a foot deep very short in length, bad wallpaper everywhere, awful brown and gold curtains... it really failed to impress. There was a fridge but an empty one; 'they don't have mini bars in this hotel'. (Very odd for such a big hotel in such a grand city) and no bathrobes, slippers etc. These things aren't necessary to enjoy a hotel (bathrobes) but I have had them in lesser graded rooms in smaller hotels, so this was a bit disappointing. Especially as it was just over $500 per night! 
As a Hilton Honours, we have also been used to a bottle of water being left in the room, maybe with a complimentary jar of nuts or sweets with a welcome note... but nothing was left here. Again, for $500 per night you would expect something.
There is actually one floor of the hotel that has been updated and one bar, but that is only one floor ... out of about 24! 
The Executive Lounge was poor. The continental breakfast was not continental ... cereals were kids cereals, some bagels, dry muffins and small pastries. A bit of cut melon and some oatmeal. No yoghurt, no meats, cheeses, eggs, tomatoes etc etc. Again, the furniture and decor was old and seriously out of date, and just all felt a bit scruffy, especially for an Executive Lounge where you would expect more... and again, considering the prices of the rooms.
The pool and gym are nice, and the changing facilities adequate but still rather dated.
I should imagine that in its day, this was all very grand but not so now. It certainly needs a facelift and for the money, a lot better service and additional touches. We wanted to love this hotel but it fell short of the mark for the cost.