"You visit Chicago now and you look at the beautiful parks and you look at the tall buildings-there's a lot of money here-and it's hard to remember that 100 to 150 years ago this was a city built on industry," she told me. "The difference between [Cleveland, Detroit and Chicago] is that Chicago diversified. Chicago kind of saw decades ago that it couldn't rely only on industry, and successive mayors Daley made an effort to have other kinds of businesses and other kinds of development."

Micheline mentioned Millennium Park as an example, the blissful waterfront green space that's probably best known as the home of Anish Kapoor's Cloud Gate, the mirrored sculpture everyone calls The Bean. Opposed by many during construction, it's now a major tourist attraction and a symbol of what sustained attention to long-term development can achieve, turning an underutilized public space into a bustling urban center.

Entrepreneurship was on view at Wrigley Field, too. I managed to catch the last half of Wednesday's Cubs-Astros game from the upper reserved seats. My ticket was just $14 and the seat was great, on the first base side above the visitors dugout. (Never mind that my Cardinals fan of a father would be sorely disappointed I was attending a game at the home of the Redbirds' regional rivals. Then again, the Cubs did lose, 3-1.)

But the seats that looked the most interesting weren't even in the park. Apartment buildings near the stadium, along Sheffield and Waveland avenues, are topped with private bleachers that once sold seats for as much as $300 each. But business has been off, and fans can now get on the Wrigley Rooftops for as little as $99, still much more than $14 but a price that includes unlimited food and brews.

Creativity is also finding a place on Hubbard Street, a strip of decidedly average nightlife joints where a handful of local industry veterans have recently opened the lovely Hubbard Inn. With classic cocktails and a couple dozen beers on draft, it's no doubt a drinking hall, but small plates-mushroom-topped flatbreads, steak tartare, grilled prawns-help keep everyone on the level. As one of the owners told Time Out Chicago about trying to do something new on Hubbard Street: "It's not your kind of turn-and-burn vodka-tonic, Bud Light place." It was a fitting location for our road trip kick-off party on Tuesday night.