09/14/2008 05:12 am ET Updated May 25, 2011

Why Chicago is My Kind of Town

Chicago is "My Kind of Town" (Frank Sinatra) and not just because I was born and raised there. It's the best big American city because it has all the advantages of bigness (great food, arts, recreation, architecture) while feeling like a small town. New York (Wall Street), Los Angeles (show business), Washington (politics), Detroit (cars) are company towns; if you aren't connected to the company, you're a bit out of the action. Boston, New Orleans, and to a lesser extent San Francisco are legacy towns; if you don't have some roots there, you're an outsider. Chicago is much more open. People in different occupations mingle more in Chicago than in company towns. Newcomers can make it more easily than in legacy towns.

All of this makes people more often feel as if they all know each other, even if they don't. There's still plenty of racial segregation and silly hierarchical thinking, but professional circles overlap much more in Chicago than where I live now, New York. And did I mention that New York and L.A. are about a thousand times more arrogant and snobby?

The biggest sport in Chicago is still local politics, which are followed more avidly than in most other major cities. But the real sports teams are doing much better in recent years than when I was growing up. On Saturday, I took my 17-year-old son and 14-year-old daughter to Wrigley Field. They have lived their entire lives in the New York area but are rabid Cubs fans. When I gave them permission years ago to root for New York teams, they declined. The day we went, the Cubs, who have the best record in the National League, got bombed by the Cardinals. We paid a fortune for scalper tickets. We were appalled that the Tribune Co., which owns the team, allowed UnderArmor (a clothing brand) to put its name on the groundskeeping gates in the ivied outfield walls. (ads are famously scarce at Wrigley). But it was still about the best way I can think of to spend an afternoon. It was my son's seventh Cubs game in 10 days, including one he attended amid a tornado.

This reminded me of my own youth. We lived only six blocks away from Wrigley in an old Victorian house that is now worth 100 times what my parents paid for it in 1962. (Alas, they sold it in the 1980s). Because the Cubs played only day baseball in those days, I was allowed to go to the ballpark with a friend and no adult supervision starting when I was only nine. (Today, they'd lock my parents up for that). Day after day, my mother would pack me lunch in a brown paper sack and in exchange for indifferently completing a few chores would give me $1.25--a dollar for admission to the bleachers and twenty-five cents for a "frosty malt" ice cream. The grandstands cost $1.50 and box seats $4.00 (an unimaginable sum) in the 1960s. (This year, scalpers can get $300 for a good box seat). I learned half of what I know about life from the Bleacher Bums, the motley collection of night-shift workers, drunks, layabouts, geezers and lesbians who frequented Wrigley in those years. In 1969, when the Cubs blew the pennant to the Mets, I would amble home from the ballpark in a state of depression. In 2003, I was back for the infamous "Bartman game," where a fan interfering with play helped cost the Cubs the pennant. Like all Cubs fans, I rationalize the pain as character-building. Besides, as we like to tell outselves, any team can have a bad century. 2008 will be different. You can bet Buckingham Fountain on it.