I like to call Chicago one of those 'unrated' parts of the US - it's not underrated as that would assume it is rated in some way; it is simply not rated in many instances. People (especially international tourists) forget about this unique city on Lake Michigan. The architecture and downtown presence of Chicago deserves its old saying of "Paris of the Prairie" derived from its wide boulevards and parks. There is endless information on Chicago's many landmarks here.
Chicago is also a city of endless summer festivals, so I would encourage you to stop by before the Winter winds arrive again.
Full disclaimer - I am from the Midwest (MIchigan) and do have a certain bias for Chicago. Having said that what I said above is 100% true. I even brought the Parisian rioter, Julie, with me on my trip, and she fell in love over just one weekend. :) Have you been to Chicago? Please send your stories...
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