Got back from Chicago on Sunday.
Definitely, take the Skyline boat ride at 9:30pm on Saturday. It is beautiful because they have fireworks over Lake Michigan with the skyline in the background.
Check out the Magnificent Mile for shopping. If you are downtown, you can get a good hot dog at Portillo's. Pizza at Giordano's or Ginos is always good too.
If you are looking for a nice but not too expensive dinner, go to Bandera on Michigan at Ohio. You can bring a bottle of wine (which is ridiculously cheap) and they will serve it to you with no corkage fee. They have live jazz on the weekend evenings as well.
I just enjoyed walking around the downtown with all of the bridges and seeing the awesome architecture.
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