I was in Chicago for an academic conference (PME-NA) so I didn't do a whole lot of touristy stuff, but what I did do I loved!
If my vote counts for anything, I think I'd choose Chicago over Manhattan any day... maybe that's blasphemous, but that's my opinion. :)
Here are pictures!
I haven't flown on a plane since I was in high school and we went to New York. It was fun.
I make it sound like I've flown other ways. I haven't. I haven't yet learned that super power.
Excuse the filthy plane windows.
And then leaving...
I really loved flying at night. Flying out of Chicago (the pictures above) was impressive, and flying into the Salt Lake Valley was pretty spectacular. I'd much rather fly at night I think.