I took the above photo almost exactly a year ago, not anticipating that New City would select the North Avenue Bridge as affording the Best view of the skyline you never expect. According to New City:
There are, of course, plenteous picturesque views of the skyline all over the place, but none whose surrounding bleakness so meaningfully contrasts with that shining city on a great lake.
I’ve seen Chicago from far too many vantage points to single one out as offering the best unexpected skyline view. I’m not even sure this one would rank high, even though it’s a great view, if only because 1,000s of North Avenue bridge crossings have made it very familiar.
A year ago the North Avenue Bridge was providing shelter and more for a group of homeless men. Perhaps the group has moved on, or New city never visited, or the view and the buffet bar were insufficient to rank North Avenue as Chicago’s Best bridge to live under.
Your nominations for best unexpected skyline view are welcome.