I had a great trip last week to Chicago for business, and it remains one of my favorite U.S. cities. I feel the same way about that city that I do about Washington- I really wish I'd spent 2 or 3 years living there in my 20s.
The strange thing about this visit was that on just about every block, I noticed something that I either remembered from a past visit, or recognized from a movie or TV show. That never seems to happen when I'm in New York- probably because I actually lived there and know the city backwards and forwards.
Also, on about four different occasions I remembered a place or thing in Chicago and thought "I wonder where that is." And every time I looked it up on Google Maps and I was only a block or two away.
One of the examples? The Lake Street Screening Room, the legendary site for Chicago movie press screenings and former stomping grounds of Siskel, Ebert and numerous others. I tried to make a pilgrimage, but unfortunately couldn't get past the front desk.
Other highlights- I ate at Pizzeria Due for the first time since 1986, and watched a Cubs game from a Wrigleyville rooftop, which I highly recommend.