It's a city of neighbourhoods. Greek town, italian town, china town, etc. There are many pockets of diaspara for you to explore.
It's also a city with a beautiful summer that unfortunately only lasts 2-3 months, and that's when people come out to have fun. The city is always growing- there is a running joke in Chicago: there are only two seasons here, summer and construction.
The architecture is also beautiful. There was a great fire in the late 1800s, and so the city was replanned and rebuilt from scratch by many famous architects. So it's not haphazard at all, and many buildings are simply breathtaking. In fact, my classmate told me the Chicago Tribune building was once voted the most beautiful building in the world.
The view of downtown Chicago from the right place on campus is amazing!
South side Chicago is a black area- that is where the university is. Famous for Blues music, and barbecue (ribs and chicken).
North side is richer, and more modern. Lots of hip neighborhoods there.
Chicago looks like the prototypical metropolitan museum. In fact, they cast it as Gotham city in the Dark Knight. Actual footage was shot there, which is why the city might look familiar.
University of Chicago campus is known as one of the seven wonders of Chicago (officially voted in the Chicago Tribune). The university was initially built to copy Oxford, but eventually some buildings- like the administration building, or the robie house next to Booth, or Booth itself, sprung up with very distinctly modern styles.