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Go to Pilsen. I like the National Museum of Mexican Art. They have a good variety of paintings, prints, sculptures, installations, photos, etc. There are bunch of good places to eat on 18th St. Just pop in one of them.
There's also Oak Park with all the Wright houses. Going out on the Green line will let you see what neo-liberalism has done for Chicago. Great views of ex-factories & slums. Then you can go visit some neo-liberal geniuses at the University of Chicago down in Hyde Park (there's also the Robie House, another Wright piece.) They've hidden the Henry Moore bomb sculpture behind the Regenstein Library, but it's worth a look.
It can be an interesting to walk around the steel-mill neighbourhoods on the south & southeast side. Not sure how much community is left.
And go see a mural by Bill Walker, Mitchell Caton, John Weber, or Caryl Yasko.
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