I was going to suggest Lou Malnatis, the architectural boat tour and the Art Institute but everyone beat me to it.

Eat really really well while you're there - it's a great foody city.

And that time of year take snow boots and a very warm coat, hat and gloves.

I wish I had more time as sounds like there is a lot to do but I have to be in Kentucky to sign my lease and pick up keys the next day so will only have that afternoon and evening, thing I will have to go back for another weekend at some point.

Snow boots and warm clothes are something I hadnt even thought of tbh! Will set them aside!