Re: tell me about your city (chicago, pdx, seattle etc)
When in Chicago you must must must go to a Cubs game. I know you hate baseball but get bleacher seats, get drunk, and chant "left field sucks" or "right field sucks," depending on where you're sitting.
Get deep dish pizza at Lou Malnati's. It's touristy, but it's probably the quintessential deep-dish pizza place.
If you want museums, the Art Institute, the Field Museum of Natural History, and the Museum of Science and Industry are all world-class.
Try to catch a show at Second City.
I'll try to think of some more stuff and post it here.
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