Chicago

The economist offers their business travel advice here.

I would add the following:

1. Chicago is an international city in the literal sense that it has a lot of immigrants and a busy airport with direct flights to many cities outside the US. A better model, though, might be that it is a very, very large midwestern town. It is in many ways more narrow minded than, say, Ann Arbor or Madison, despite the size difference.

2. When I was there in graduate school it always seemed to me that Chicago had an amazing number of people who viewed the world as a zero sum game, so that the only way they could get ahead was by taking advantage of you. In this sense, Chicago is the opposite of LA, which I think of as the city of the positive-sum deal.

3. I always thought of Chicago as a lazy city rather than a hard-working one but that may be due to interacting more with government workers than with corporate types downtown. Chicagoans pay for a lot more city and county government than they actually receive. It seemed like every year one of the local TV states would do an expose on some sort of city worker where they would tail them on their daily rounds and find them spending a good chunk of the day sleeping in their city vehicle on some quiet sidestreet.

4. The woman who cut my hair at "Hair Ph.D." in Hyde Park used to return to her old neighborhood in the city to vote for Daley, even though she no longer lived there (or, indeed, anywhere within the city limits).

5. The two things I came to like about Chicago were the amazing amount of high quality, low price ethnic dining, much of it in neighborhoods scattered around the city rather than downtown, and the terrific theater scene. In regard to theater, my experience was that quality was more or less unrelated to price. The best piece of theater I ever saw cost five dollars, took place in an old warehouse, and my friend and I were the entirety of the audience.

The poem about Chicago I wrote my first year of graduate school is here.