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I would check out ESPN zone or Dave and Buster's. Both serve alcohol, but you can be in the place as long as you are 18+. I don't know if you have those places by you, but they are pretty cool. Where in Chicago are you going to be? I could probably suggest an establishment or two that will not ask for ID's.
Other than that, I say be a tourist and check out the Sears Tower, and Chicago has some of the best museums in the country.
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