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These Political Corruption Walking Tours Of Chicago Are Selling Out Fast

By Rachel Cromidas in Arts & Entertainment on May 2, 2016 9:07PM

Paul Dailing is giving walking tours of Chicago's political corruption landmarks. Photo via Paul Dailing.

Chicago has its share of architecture tours, boat tours, walking tours, ghost tours and even an "Untouchable Tour" of Prohibition-era mob hangouts. Now, it also has a tour devoted to the seemingly endless political corruption that has, for worse or worse, defined our city over the years.

"There's this vague, ethereal notion that every politician in Chicago is going to go to prison one day," Chicago area-native and journalist Paul Dailing told Chicagoist, because political scandals are just so common. After all, Chicago's judicial district features the most corruption in the U.S., according to reports, and local professor Dick Simpson called 2015 a "banner year" for corruption in Chicago.

Dailing has packed decades of political scandals and white collar crime into a rollicking walking tour of downtown Chicago with a mix of obvious stops—City Hall, the Dirksen Federal Courthouse—and some hidden haunts that represent how deeply political corruption is embedded into the city's history. That means, in addition to discussing some of Illinois' recent problematic favorites, like jailed ex-governor Rod Blagojevich, Dailing guides his tour through perplexing Tax Increment Financing (TIF) districts and gerrymandered aldermanic wards. He hopes these stops will help attendees connect the stories about politicians behaving badly to their own lives.

"You can talk until you're blue in the face about a TIF district, but I think it might click when people are standing in front of the Bloomingdales downtown, that gorgeous old building in a ritzy district, and you say, this received $12 million from a program designed solely to revitalize urban areas," Dailing said.

The tours starts at the site of the Workingman's Exchange—a Loop bar from the turn of the century that was run by a corrupt co-alderman (Chicago used to have two aldermen per ward back then) who used to buy votes with free beer. It also hits up another bar, once called the Mirage Tavern, where undercover journalists conducted a sting operation to catch city inspectors trying to shake them down for money.

Dailing, a journalist himself who lives in Bucktown and blogs at 1,001 Chicago Afternoons, works as a tour guide around Chicago when freelance work is light. He said he researched the details of the tour extensively in the Chicago Tribune and Sun-Times archives and at the Harold Washington Library before putting it all together: "I always try to have first-hand sources when possible; if you don't go to original sources, you might as well be reading the Wikipedia entry," he said.

But as he got deeper into his research, he ran into an unexpected problem: New political corruption scandals were happening around Chicago and Illinois faster than he could keep up with.

"I'd read the paper and think, crap, now I've gotta talk about Barbara Byrd-Bennett; crap, now I've got to talk about Denny Hastert," he said. "Chicago corruption would not slow down enough to let me chart it."

The first of Dailing's Chicago Corruption Walking Tours kicked off last Sunday, and they quickly sold out. He's added more tour dates for the spring and summer to his website, and they're filling up too, but some spots are still open. Half the gratuities from the tour are being donated to City Bureau, a new local journalism endeavor.

Paul Dailing is giving walking tours of Chicago's political corruption landmarks. Photo via Paul Dailing.

There's been a lot of buzz around the tours, but Dailing says his goal is to get people thinking about the city's problems for more than just entertainment value.

"There's so much political corruption that barely merits a shrug in Chicago, so I want to bring attention to them in new ways, [to show] that this isn't cute, this isn't the Chicago way," he said. "It's about reminding people both that the system is very messed up, and that we keep catching these people, but vigilance is the watchword."