Corruption Tour

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From today’s convict governors back to the shady 19th-century land deals that turned mud into metropolis, Chicago has a centuries-old tradition of graft, kickbacks and corruption.

Former newspaper reporter Paul Dailing pulls the curtain back on these vanished stories through the Chicago Corruption Walking Tour.

The Chicago Way Package

The Chicago Way Package ($20) covers about a mile, ending at the State Street Bridge.

You’ll learn:

  • How a land scam built the Midwest
  • How early 1900s aldermen bought votes with free beer
  • How blackmail built the Loop
  • About FBI stings, jailbird governors, gangster aldermen, patronage, gerrymandering and more!

The Bleepin’ Golden Package

Those who choose the Bleepin’ Golden Package ($30 total, or an extra $10 the day of the tour if you want to continue) will keep going to the Chicago Brown Line stop, for a total 2.25 miles.

You’ll learn:

  • How a king-hating mayor distracted from Al Capone
  • How a program meant for low-income neighborhoods funds luxury downtown shopping
  • Why a newspaper bought a seedy bar
  • About lakefront land grabs, parking meters shenanigans, hired trucks, TIFs, a fish that could climb a tree and more!


Each year, half the tour gratuities are donated to a different nonprofit newsroom or investigative journalism group working in Chicago. We’ve collected money in years past for City Bureau and ProPublica Illinois, but this year the funds will go to The TRiiBE, a digital media platform helping to reshape the narrative of black Chicago through journalism and art.

Press Coverage


NBC 5 Chicago

DNAinfo Chicago


Chicago Magazine

WBBM Newsradio

Columbia Chronicle

WLS 890 AM


Boing Boing

Journal Metro

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