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In Chicago:
- Go to Navy Pier. While there, eat a hot dog and have a beer at the beer garden.
- Eat one slice of deep dish pizza at Giordano's. Try one slice - if you don't like it, their NY Style isn't too bad either.
- Stand on the SkyLedge at the Sears Tower and try not to fudge your undies.
- For a nicer meal, try Frontera Grill in the restaurant district. Nice jeans/nice shirt attire can pass but best to be business casual.
- Eat another hot dog at Portillo's.
- Do one of the river cruises. The best is the Wendella. When going past my office building, wave. There will probably be a guy in a brightly colored polo shirt freaking out waving with both arms outside my building, but only if there are kids on your boat.
- Go to the American Girl Store at the Water Tower Place. If you're with a guy, drop him off at the Apple Store down the street.
- Go to North Avenue Beach. You can get hot dogs and italian beef sandwiches there, too.
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