Fascinating effect. It must be fun to live in a house of mirrors. The structural engineer in me leads me to think there's quite a bit of thermal growth and shrinkage in these buildings. Given the temperature swings and wind loads in Chicago, the buildings have to be appropriately designed for all kinds of natural effects and movement. The Big Red building (likely in your view) had quite a time with this and every window had to be replaced - not cheap!
@stray_shooter Your description makes me think of these reflections as giving us a window into the interior thoughts of the buildings, if they had any! I've always wondered about the "red" building -- I never have heard of it called anything other than that, but assume it must have a name. On our condo board, we're dealing with the Dept of Transportation as they have plans to start adding a lane on each side of the Dan Ryan, right next to our building, so huge concerns about structural implications there.