I am taking a trip to Chicago (without the kids!) and plan on doing lots and lots of walking. I went last year, it was a dream. I wore these shoes: boots with heels.
My toes froze. And my feet hurt for days afterward. I ended up limping around the city. When I went to the Chicago Institute of Art I gave up and wore my running shoes. I am classy like that.
This year I was on the look out for a new pair of shoes for my Chicago trip. Criteria: Warm (since Chicago is FREEZING) and comfortable. I found these little beauties. They look like normal shoes: