Things I did in Chicago that you should too:
1. Take the train alone, feel accomplished because you didn't get lost.
2. Walk into the Hilton on Michigan Ave. Act like you belong. Get free information from Concierge.
3. Wear a scarf.
4. Take a Bus Tour! (I will always recommend bus tours).
5. Answer bus tour guide's questions, he becomes less disgruntle this way.
6. Go to the Art Institute.
7. Understand that the video-art-clown-room is supposed to make you feel uncomfortable it is the point of it.
8. Make fun of clown room with people from Michigan.
9. See a Show at Second City.
10. Get a little buzzed on $9 spiked coffees at Second City.
11. Make nice with table mates at Second City, get shots bought for you.
12. Hug your friend goodbye and say "thank you."