On all three of my visits to The Art Institute of Chicago, I end up going straight up the front stairs and heading to the Impressionist Gallery, where I end up spending the majority of my time. This museum has a great collection of Monet's, Renoir's, Degas's, and of course the ultra famous "Sunday Afternoon on the Island of La Grande Jatte" by Seurat. The Impressionist gallery is worth the trip alone, but they do have an interesting collection of other periods as well (especially the neoclassic section). Winslow Homer is well represented (if you are interested in that sort of thing), and there seemed to be a wide selection of Modern American Art. I have never seen the contemporary wing of the museum because it has been under construction for some time, but I have high hopes for that in my next visit.
Plan what paintings to see ahead of time http://www.artic.edu/aic/visitor_info/selfguide/index.html
A great, inexpensive experience that helps connect you to the artistic spirit of humankind.
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