Perfect for the night!
I stayed in a double room at the Sheraton Tower on Dec. 1st. My traveling partner scored this as a mystery deal, I BELIEVE on Hotwire. $130 before taxes for the night. 
We wanted to eat at the steakhouse but we did NOT have reservations. There is a lot of local dining options but have it picked out ahead of time or you will be wandering the streets like we were. I would've been fine with anything but my other half had pickier taste buds. We didn't check out the other options so I have no input on those. 
The bed was amazing, as usual. LOVE Sheraton's beds! The furnishings were refined, yet casual. It was a compact room, but fine for one evening. 
The location was fantastic. Walking distance to many things. We saw a BEARS game the next day and just walked back after the game. Not a problem at all HOWEVER, in cold weather, you won't want to do this. Also, if you have kids you won't want to do this, as there are a few bridges you pass under and the homeless call that home. They minded their own business though while we passed through.
Used self-parking and had our spot for right about 24 hours for $45. It was safe, well-lit, no complaints there. 
All in all, I would definitely stay there again! We asked for a water-view and ended up with a Navy Pier/lakeview - but keep in mind, it's a sparse view of the lake, you are seeing everything between other buildings. 
Nice choice for a short stay. Might go for a king room (we had another couple along this time) for a longer stay.
Enjoy!