Hands down the most festive bar/restaurant you will find in Chicago - you will find lots of Christmas decor and 45,000 lights strung throughout. Lunch is served during this day, but this turns into a bar at night. It gets crowded but it's worth the wait!
There are plenty of shops along Michigan Avenue (north of the hotel). Water Tower Place, Shops at North Bridge, and 900 North Michigan are indoor malls and a great place to avoid the cold! If you are heading south of the hotel towards Millennium Park, you can stop at Macy's on State Street - it is very festive at Christmastime.