I grew up near Chicago. In the suburbs, to be clear, one called LaGrange Park.
I went away to college, and never moved back. Mary, who grew up near Toledo, sometimes agitates for us to move to Chicago. We both love the city, and could easily move to some hip area like Bucktown. Or, at least, so we would like to think. When I visit my brother Pete, who lives in Evanston, we often spend a day walking through the city, looking at buildings and stopping in at bars. The city of Chicago has some of the best urban structures in the world.
But a city isn't just its urban core. It's everything around it, the whole vast metro area. Chicago has one of the vastest metro areas in the country, and, not to put too fine a point on it, it sucks. According to the linked newgeography article, it is the third largest urban agglomeration in the world, after Tokyo and New York. It is less dense than Los Angeles.
Aside from Lake Michigan to the east, there is nothing to block its growth. The land is flat and easily dug, and the lake supplies an increasingly rare resource, one that will eventually be the limiting factor in urban development worldwide: fresh water. The buildings range from undistinguished to ugly and the distribution is almost entire automobile oriented. And--not the fault of development--there really aren't many scenic features. Exactly what made it great farming country makes it uninteresting to look at.
The great thing about the Boston metro area is that you can leave it, and pretty fast. And the areas around it vary. Going up the rocky North Shore is noticeably different than traveling through the glacial outwash plain to the south, or the hills to the west. Snooty zoning restrictions in older towns keep me from ever being able to afford a house there, if that was the life I wanted, but provide me with picturesque landscape to bicycle through.
I keep seeing articles about the new urbanism, and people moving back to the urban cores. I have no idea what world they're talking about. What's needed is a New Suburbanism, since that's where almost everyone in the world will eventually live.
So despite the fact that Chicago bars are some of the best in the country, I'm going to remain a visitor. And I think people who live there will be sorry someday about the choices they made without even knowing they were making them.