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by YardDancer_Archive
The Taste is too expensive, and none of the vendors are on point because they have to prep the food portable-style and serve it to hordes of sweaty fools. If the portions were actually tasting-size, then I could see how it would be worthwhile, because then you could try a variety of different items. Instead, you are mostly stuck with full-size portions, and if you want to try many items, you're going to throw a lot of food in the trash.
I would say that our two most notable street foods are the Chicago-style hot dog, and the Italian beef sandwich with gardinera. There are loads of good restaurants here, but as far as things that you would want to eat while standing up at the Taste, those are the main two items. Anything else you could eat there, you would be better off eating in a restaurant.
If it's convenient, or you are in the mood for some festival atmosphere, then by all means, do it. But don't do it for the food.
Edit for non-Taste-related Chicago items. In my mind, these some iconic Chicago activities:
Architecture in the Loop
Art Institute
Grant Park
Mexican culture in Logan Square and/or Pilsen
Chinese food at one of the good restaurants in Chinatown (do research)
Given the weak dollar, maybe try record shopping at Dusty Groove (soul, jazz), Jazz Record Mart, or elsewhere (for rock, the Reckless Records in the Loop is not the best, but surprisingly good given its central location).
There is obviously a lot that I'm leaving out... Some really incredible stuff is a bit further afield and if you have really specific interests, you may want to rent a car. Chicago is a rangy beast, and the CTA, while OK for what it is, doesn't offer complete coverage.