Hello Brent,
Chicago is a terrific place for many types of photography. But, alas, we have no "landscape" in the conventional definition. Cityscapes, yes!
Contrary to popular mythology Chicago really doesn't have an abundance of abandoned, blown-out neighborhoods. We're a very vital city today.
Also, contrary to Alexis' tip I -really- do not recommend taking an unescorted trip through neighboring Gary, Indiana at any time of day. There are plenty of pathetic scenes of abject poverty over there, and some very compelling working steel mill scenes. But it's just not a safe place. Lots of idle men, lots of drugs, lots of anger.
Poke around in
my personal galleries, as most of the images are Chicago-origined. If you see scenes that you might like to visit feel free to send me a note to learn more about the location and logistics.
Enjoy your upcoming visit to my city!