Chicago, well, the unique bits of Chicago, are nearly impossible to photograph. The magnificent mile is truly amazing, in a way photos don’t really capture. Chicago’s people have found a way around it: the Cloud Gate, aka “The Bean”. It’s an incredible piece of sculpture that is not only lovely as an object, like all great art it makes you really look, and lets you see the world around you in a new light.
To make it short, I think the best way to photograph Chicago is: in reflections.
P.S. I admit I’m strictly a point and shoot photographer. If you’ve made a great shot of Chicago, post a link.