Tour guide and journalist Paul Dailing outside a federal building on Sunday talking to tourists about corruption in Chicago and Illinois. Dailing has started a new weekly walking tour in downtown Chicago. REUTERS/Fiona Ortiz

CHICAGO — While designing a walking tour of Chicago focused on corruption and political shenanigans, journalist Paul Dailing watched new scandals pop up at a rate that only reinforced the city's reputation for rackets and rough politics.

Just in the past year, the CEO of the city's schools pleaded guilty to wire fraud and the police chief lost his job in a scandal over police shootings of black men. Then, last month, former House Speaker Dennis Hastert was convicted of a financial crime and admitted to sexually abusing high-school wrestlers in Chicago's suburbs decades ago.

There was no way Dailing could stuff all the new cases into the three-hour weekly downtown tour he launched in April. After all, he had to cover two centuries of graft, embezzlement, blackmail, patronage, vote-buying, gerrymandering, and scams.

But he ties them into a culture of corruption that has hurt the city and the state of Illinois.

"I love sharing these stories with people," the 36-year-old Dailing said.

He said the internet had changed tourism, creating niches for people with a particular passion. "People can find tours as nerdy and as specific as they want."

Twelve people interested in local history signed up for a chilly Sunday tour that began outside the former location of a bar run in the early 1900s by Alderman Michael "Hinky Dink" Kenna. Along with a partner, Kenna set up fictional entities to grab city contracts that they resold to companies, among many other shady activities.

Two stops later on the 2 1/2 mile tour Dailing pulls laminated cards out of his satchel to show the group Chicago's absurdly gerrymandered electoral districts, often along race lines.

He dives deep into the stories of the seven Illinois governors who have been charged with crimes, including four who have gone to prison since the 1960s.

Former US House Speaker Dennis Hastert arriving at the Dirksen Federal courthouse for his sentencing hearing in Chicago. Thomson Reuters

Even for Chicagoans steeped in their city's history, the tour was an eye-opener.

"You always hear about how Chicago is so corrupt, but I didn't know about all the details he's going into," said Kara Hart, a financial controller at a technology company, who went on Sunday's tour.

Some mobsters are included, including Fred Roti, a made man in the Mafia who was an alderman for 23 years and was convicted of bribery and other crimes.

But don't expect the tour to stop at the staircase from the big shootout scene in the "Untouchables" movie. Dailing wants people to stop romanticizing Al Capone and to realize how gangsters have hurt Illinois by fostering a culture of corruption.

"I hate this city's stupid love affair with Al Capone," he told his avid listeners. "I hate that people think of him as a folk hero."