It’s no secret that Chicago has, well, should we say an interesting and rich political history. Hell, I voted three times in the primary held in February. I didn’t, but though some of the scandal inherent in the city has diminished, the political climate in Chicago still blows cold and shady.

Take, for starters, the trial of political fundraiser Tony Rezko who has been federally charged with extortion, money laundering and fraud and from whom IL Senator and presidential candidate Barack Obama has been scrambling to disassociate himself. Cook County, of which Chicago is the largest city and from which cities are actually contemplating seceding, recently passed a heavily protested county budget spearheaded by an unpopular Board President. One only needs to view the recently released film, Chicago 10, to see how the city botched the 1968 Democratic National Convention. How about the fact that an expressway literally divides the city’s white and black citizens? And while the road to a possible Chicago 2016 Olympics is no doubt paved with back-door deals, nepotism and greasy palms, Chicagoans should not worry. George W. Bush believes that the Olympics is a sporting event and not a political event. This is good news because past Olympic hostage situations, bombings and the more recent torch relay attacks led me to believe that the Olympics is indeed a political event.

Every town, every city, every country has its own political, racial, and gender climate. In many places it’s easy enough to ignore or miss, but a traveler who wants to get the full local flavor would want to be aware of such things. While visiting a friend’s family in Ireland in 1998 I learned that, while I was there, the whole country was voting on The Good Friday peace agreement. It was a monumental event that I wasn’t prepared to fully absorb as I had no knowledge. A few years back in Memphis, Tennessee, my girlfriend and I were playing pool with another couple at a local lesbian bar when the couple abruptly left telling us, “It gets awfully dark around here at midnight.” We realized, as a number of African-American women began arriving at the bar, that the couple had been referring to the race of the clientele. We were appalled that we had spent any time at all associating with that couple, and felt blindsided by having met such openly racist, local individuals. I have since learned about the experience my grade school best friend has had with race in Memphis where she now teachers. She e-mails me that she feels a definite divide, and that it isn’t like our grade school experience. The black and white kids aren’t best friends like she and I had been, which she was very saddened to learn, as was I.

So my question is, how does a traveler prepare for whatever may be going on subtly or not-so-subtly during her/his visit? Obviously, talking to locals before and during the trip provides a wealth of knowledge. Local, independent newspapers, many of which are now online, are good sources, as well. A few ideas for Chicago visitors would be to check out the Chicago Reader (not quite as independent as it once was), particularly its Clout City blog, and The Chicagoist which is a great blog that reports the goings-on with a lot of bite. I’d love to hear what other sources people use, in the states and internationally, to dress for their destination’s political climate.