Chicago really isn’t my kind of town. But, back in the summer of 2017 I was there once for a 23 hour layover between the Southwest Chief and the Empire Builder trains. Because of the height of the buildings it is hard to get a perspective to take a photo that gives a sense of being there. All of these were taken either beside or from on the water.
The one tourist thing we did, aside from just walking around, was to take an architecture cruise. The following two were taken on that trip.