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August is a very very slow month out here. At least from what I've heard and seen. A way to look at Chicago is when good conventions are coming, and what areas the conventions are in. Perhaps on your next tour you can book two places large conventions are going on at the same time near the conventions. Just do a day near one, then a day near the other one... Best of both worlds

well if u were at ohare and it was several years ago u can give it another shot
ohare or Rosemont was pretty much dead if no convention going was just hotels but the last several years has exploded in building up a entertainment center. It is now full of entertainment and now is a happening place at any given time.   The casino was the start and now has a central location for many restaurants bars clubs theatres etc.   Its like night and day so u may give it a shot.  But since u like swest at midway that's a long haul.  midway is still in middle of nowhere and if u travelling to ohare or Schaumburg or oakbrook when on short weekend trip good luck cause u will have long travel times .    
if u like Asian chicks then ohare is a hub but actually oak brook and Schaumburg are Asian areas too.

Cayden is a provider.