My wife and I stayed at the Sofitel Watertower in Mid-September.
Nice place and some rooms have a great view to the John Hancock tower and the lake. You can ask for one at check-in.
It's a block west of the Hancock and the northern end of Mag Mile.
We had dinner one night at a great place called Carmine's at 1043 N Rush St.
Rosebud Restaurants Navy Pier is a waste of time.