Millennium Park is great, or just strolling around anywhere downtown really. Navy Pier is maybe a little touristy, but there are some great skyline views there as well. Shedd Aquarium is HUGE... first time I went I realized that I missed another area and barely scratched the surface. Thankfully, I got in for free with my United (technically SkyWest) ID so it's not like I wasted a ton of money.
Ok, Chicago. Food. Man's gotta eat, right? Now, you will need to have at LEAST one of the following: Italian beef, Chicago-style hot dog with all the condiments, deep dish pizza. The first two are readily available at Portillo's, a local chain. Hot Doug's seems pretty good as well, but I haven't been there. Pizza is a personal preference. You've got the original Uno's (which is right next to Deux, basically an "expansion" across the street), Gino's (Geno's?) East, and Giordano's. The second two are also local chains, I'm almost positive. I prefer Giordano's, personally. Also heard good thing about Lou Malnati's.
That should get you started. Give me some more information about your preferences and I'll see what I can do. I've only been outside of the airport maybe 4 short times before, plus a couple times driving through, but it's a great city. Been meaning to go back for a while, though it's a bit of an "easy" city for United that's easy to kind of ignore ("I can go there anytime...")
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