Prohibition Chicago: Myth vs. Reality Walking Tour
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Discover the truth behind the stories of Prohibition-era Chicago on this engaging walking tour. Over two hours, you'll explore the city’s notorious vice districts along the Chicago River and the South Loop, learning how these areas fueled the rise of organized crime and shaped the city's history.
Hear about legendary figures like Al Capone and the infamous Beer Wars, culminating in the St. Valentine’s Day Massacre. The tour also highlights Chicago’s vibrant jazz scene during the Roaring Twenties and how the city’s culture has been portrayed in movies like "The Untouchables" and "Chicago."
While the tour includes stories of murder and sex work, it offers a fascinating glimpse into a turbulent period. Parents should use discretion for children under 15, but all are welcome to join this vivid journey through Chicago’s past.
Frequently asked questions
How long is the tour?
The tour lasts approximately 2 hours.
What language is the tour conducted in?
The tour is conducted in English.
What is the group size?
Groups are limited to up to 15 participants.
Is the tour suitable for children?
Children aged 0-13 are welcome, but parents should decide if the content is appropriate for those under 15 due to mature themes.
What is included in the price?
The tour includes the entrance fee to the sites visited.
Are there any exclusions?
Gratuities and bottled water are not included.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 2 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Entrance fee
Not included
- Gratuities
- Bottled water
Itinerary
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Stop 1
As we stroll the Riverwalk (or Wacker Dr., depending on crowds), we'll discuss the rise of vice districts and organized crime in Chicago, and how the city played a role in the fight to ratify the 19th Amendment, which ushered in the Prohibition Era.
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Stop 2
Now a restaurant named after a beloved sportscaster, Harry Caray's Italian Steakhouse was where Frank Nitti, Al Capone's bodyguard and successor as head of the Chicago Outfit, lived for a while. We'll talk about how he's been portrayed in the movies hasn't always been accurate.
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Stop 3
After crossing back into the Loop, we'll talk about the role Chicago played in the popular and artistic growth of jazz during the Roaring Twenties. We'll stop at the site of a now-demolished place where Capone and jazz intersected.
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Stop 4
The Chicago Theatre was built in 1921 and its marquee is an icon of the city and featured in dozens of movies and TV shows set in the city. We'll discuss women who inspired the hit musical "Chicago" and its many versions.
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Stop 5
A hotel whose history dates back to 1870, the Palmer House was renovated and expanded in the mid-1920s and remains a symbol of that era's wealth and elegance.
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Stop 6
Opened in 1897 as the city's first public library, the Chicago Cultural Center was featured in two key scenes in "The Untouchables."
Meeting point & pickup
Meet at the starting point
We'll gather in the plaza on Michigan Ave., between the Tribune Tower and the Apple Store. Here, we'll discuss the early non-Indigenous settlers and how they contributed to Chicago's growth.
Open in Google MapsCancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day before
- 0% refund if cancelled within 1 day
Instant confirmation
Your booking is confirmed immediately after checkout.
From $35.00 per person
- Free cancellation
- Secure checkout with our booking partner
