Here is one example of the photos I have of the Chicago skyline from St Joe. You'll have to click on the image to see it larger.
I suspect there are a few factors that have to come into play for a good viewing.
- Crisp, clear air
- Clear skies over Chicago
- A calm lake
- Low lake levels
- Knowing where to look
The image above was taken at sunset on December 4, 2012 from Lookout Park in St Joseph.
Whenever I take in a Lake Michigan sunset I look to the southwest to see if I can see Chicago. And every once in a while I get lucky.