I can answer for Chicago bc I live there... Check out the Art Institute museum, the Shedd Aquarium, the planetarium, Navy Pier, north avenue beach. There are a lot of free things to do as well. We have festivals all summer long and the music scene is amazing. Its not hard to find things once u are in town bc there is a paper called the Red Eye that is free and you can pick it up all over town and see what is going on. Chicago is awesome.
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