dot boatsby
GaiaComment: I understand why you entered this, so I won't go into whether it meets my reading of the challenge rules.
Lighting: This is a tough time of day to shoot, the bright sky throws the buildings into darkness, and makes the image feel bottom heavy. I would suggest cropping quite a bit lower, maybe a cm above the top spire. The sun on the water is broken by clouds, and for this type of shot you need the water to be uniform.
Composition: A panoramic shape (long, narrow rectangle) would help this image look more honed. Cop out the sky as described above, as well as the left 1.5 inches of the shot (where the land jutts into the water in a zigzag) and the right edge up to where the beach/shore is lit (just to the right of the tall building). That will get rid of the distracting elements and fosuc the image on the water more.
Subject: I think a big issue you ran into here is that the subject of this image is actually the skyline, not the boats. if you could get down further, so we would see some detail in the boats, or give up the "dot" idea and take a shot from the water level, this would be more about boats and less about Chicago.
You have a great start here, and obviously have access to a way of taking skyline shots, so keep trying and you'll get it. One tool i use in landscape/cityscape shots is the crop tool in PS, not to actually crop, but to experiment with hiding parts of the image and see how certain elements add to the photo or distract from the subject. Turn the opacity of the crop tool to 95% and fiddle with it, you'll find it helps you frame your shot, and sometimes you will even find two distinct shots in one photo. I encourage you also to shoot in the largest file size you have when doing these, not only do skylines blow up well, the large format allows you to take multiple pieces from the photo (One cool looking building, a section of sky, or the very tops of the buildings) for use as prints without losing as much detail.
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