Since it is in Chicago, I would do the Buckingham fountain, look up the photos on the web, I think that would be pretty extreme yet relate to Chicago. Do not do the obvious, like the Sears Tower, or A Lincoln, or JH building. BUT that is just my opinion. I think the downtown skyline would be a lil too much, there are many buildings involved. The stadiums are played ALOT on his show, so he may want to look for something totally different. I wish you the best and good luck, Sincerely, Veronica
PS You can always go political, or do something related food wise, they have the Taste of Chicago, u can do Eli's Cheesecake, Connie's Pizza, Maxwell Street, etc soooooooo many endless possibilities, I was born and raised there.