Convicted politicians, mobsters, shady real estate deals and more. That's what you'll see on this walking tour of Chicago corruption-filled history.


Paul Dailing, a 1997 graduate of Auburn High School in Rockford is your guide for a tour detailing Chicago's dark past. The Chicago Corruption Walking Tour is one the city's most popular tours. The tour is sold out through September.

According to, you're in for one whopper of a tour due to the fact Chicago has been up to no good, for so long. The tour will be in two parts.

The Chicago Way package includes:

  • How a land scam built the Midwest
  • How early 1900s aldermen bought votes with free beer
  • How blackmail built the Loop
  • Undercover FBI stings
  • Jailbird governors
  • Gangster aldermen and more

The Bleepin' Golden package includes:

  • How a punk club turned into the center of River North ritz
  • How a king-hating mayor distracted from Al Capone
  • Why a newspaper bought a seedy bar
  • Lakefront land grabs
  • Parking meter shenanigans
  • Hired trucks
  • TIFs
  • A fish that could climb a tree and more

The Chicago Way package is $15 and the Bleepin' Golden package can be purchased with 'Chicago Way' for $25. And half of your gratuities will go to help help City Bureau ( train young journalists from the city's South and West sides. As you'll learn on this tour, Chicago needs all the watchdogs it can get.

What are people saying about Paul's tour:

Cynthia B. writes,

This walking tour was a lot of fun. I took the extended tour which brought us all over downtown Chicago. The tour guide was Paul and he is extremely knowledgeable about the topic. But he wasn't dry or unapproachable. He presented all the facts in a very relaxed and funny way so it was almost like hearing juicy gossip and not boring history. (I they taught history like that in high school kids would be much better in history.) I would recommend this to anyone who enjoys taking tours of Chicago like the river tours and wants something a little different. But, be sure to wear comfortable walking shoes.

Kari M. writes,

Paul was detailed and smart. This was was an entirely different take on our city...centuries of corruption revealed. So interesting!

Sean G. writes,

Smart, funny and informative. I have lived in Chicago for a long time, and I thought I was well versed in the city's corruption... I was wrong. Paul is an excellent guide, has wonderful insights into the city's past and I highly recommend taking this tour.

Since this tour is SOLD OUT through September, you'll want to get your name on a waiting list. Click here.

Be sure to check out Paul Dailing's blog, 1001 Chicago Afternoons