The Horseshoe is a nice enough casino, but I wouldn't really recommend the drive unless you can't get any live poker action back home.
I think frosst is talking about Navy Pier when he says there's a boardwalk. I highly advise against going there. It's a tourist trap of the worst kind. I guess if you're walking along the lake, sure, take a walk around the perimeter, but really, there's not much else of value there unless tourist stuff is your thing (and you know.. to each his own, not judging.)
Haven't been to Kuma's myself, but I hear great things about it.
Not sure if one of their dates will coincide with your visit, but if you like to dance, or just want to check out an crazy party, hit up the Empty Bottle when these guys are DJing: http://windycitysoulclub.com/ It's like a club, minus the shit music, pretentious assholes, stuck up girls-- pretty much without all the things that make clubs shitty. Empty bottle is also just a cool bar in general, and has an attached restaurant that has pretty good food.



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