Chicago exhibits many aspects of what the city design folk are calling "urbanity." I spent most of my time downtown; the conference was in the Loop, and my hotel was in the River North area. Pedestrian traffic is everywhere, and there are a lot of work places, places for serious recreation like theaters and museums, and a huge number of coffee houses and restaurants. The sidewalks are wide, with buildings mostly built up to the sidewalk. The few exceptions make for a nice variety. The building across Jackson St from the Willis (formerly Sears) Tower actually has a lovely lawn, but for urbanity's sake that's definitely the exception. This is a section of Jackson St looking west, by the well-famed Intelligentsia Coffeehouse.
Note the amount of car traffic, and street width, both probably more than the new urbanists would like. Interactions between pedestrians and cars were mostly peaceful, though there were frequent examples of aggressive action by both.
Downtown Chicago has many places you've heard of, so I'll skip those and talk about my quirky favorites. Friday morning I had breakfast in the food court at the Merchandise Mart (1928). There are many oatmeal options, and the CTA stop exits right into the gigantic office building.
Friday night I saw a movie ("Jazz on a Summer's Day") at the Gene Siskel Film Center, hidden in the middle of the block on North State Street, but once inside a great place to see movies that never come to Cedar Rapids. Sunday morning I worshiped at First United Methodist Church downtown, housed in "Chicago Temple" (1924), a skinny skyscraper on Washington Blvd. The church is vital and active, acoustically live, with an impressive music program and (are you sitting down?) no video screen.
I made a couple forays into the suburbs, seeing the downtowns of Downers Grove and La Grange. Both seem to be in fine shape (as is Naperville's, which I visited in January): commercially active, nice layout, though I suspect that if I did a careful survey I'd find they tended towards the tony-upscale over the practical. Maybe not. All three are 19th century towns that became suburbs when the metropolitan area's reach took them in. I didn't visit any more recently-created or less-wealthy towns.
Even so, signs of sprawl are everywhere in metropolitan Chicago. The metro area extends for miles beyond the city limits, and takes in numerous suburbs of ever-decreasing density. Understandably, a former student who recently moved to Chicago from Montana complained about the lack of nearby wild areas.
The area's reach has long since engulfed the small towns along Route 30: Sugar Grove, Big Rock, Hinckley, Waterman and Shabbona. From the perspective of my car on Route 30, Hinckley and its traditional downtown seems to be making the adjustment well. Waterman, by contrast, is building a gigantic subdivision east of town with cookie-cutter houses, all large on large lots, and connected to nothing. As a society, we have a long way to go to achieve sustainability. In tiny Waterman, even for destinations that aren't a long way off, they'll have to get there by car.