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Prohibition Chicago: Myth vs. Reality Walking Tour

4 Reviews 5.00 out of 5 stars Based on 4 traveler reviews collected by Cool Shore Excursions and TripAdvisor | Recommended by 100% of reviewers | Chicago, USA
Don't miss out!
On average, this is booked 31 (0) days in advance.

2 hours (approx.)
Mobile ticket
Offered in: English
Instant confirmation

Overview

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always accurate.

On this tour, you’ll hear how the culture in turn-of-the-century Chicago helped bring about the 18th Amendment through stories of notorious vice districts along the Chicago River and the South Loop. We'll talk about the rise of Al Capone during the infamous “Beer Wars,” culminating in the St. Valentine’s Day Massacre. Along the way, we’ll talk about how the city played a role in the popular and artistic growth of jazz, and how Chicago during the Roaring Twenties has been depicted on screen, in blockbusters such as "The Untouchables" and "Chicago."

Please be advised that this tour contains stories of murder and sex work. Although children are welcome on this tour, parents should use their discretion in determining whether it is suitable for those under 15.

What's Included

  • Entrance fee
  • Bottled water
  • Gratuities
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Meeting Location

Meeting point

401 North Michigan Avenue
Chicago, IL 60611, USA

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Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

230 North Michigan Avenue
Chicago, IL 60601, USA

The Art Deco design of the Carbide and Carbon Building is not only beautiful inside and out, but it also holds a secret related to the era.

What To Expect

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Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
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Chicago Riverwalk

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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30 minutes Admission Ticket Free

Harry Caray's Italian Steakhouse

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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10 minutes Admission Ticket Free

100 W Randolph St

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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5 minutes Admission Ticket Free

The Chicago Theatre

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 talk about women that inspired the hit musical "Chicago" and its many iterations.
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10 minutes Admission Ticket Free

Palmer House Hilton Historic Lobby

A hotel whose history dates back to 1870, the Palmer House was renovated and expanded in the mid-1920s and remains an example of that era's wealth and elegance.
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15 minutes Admission Ticket Free

Chicago Cultural Center

Opened in 1897 as the city's first public library, the Chicago Cultural Center was used in two crucial scenes in "The Untouchables."
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15 minutes Admission Ticket Free

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Additional Info

  • Confirmation is instant and will be received at time of booking
  • Wheelchair accessible
  • Transportation options are wheelchair accessible
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller

Frequently Asked Questions (7)

Q: What is the cancellation policy for the Prohibition Chicago: Myth vs. Reality Walking Tour?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CST). Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

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Activity code: C-5659897P7

Traveler Photos

Reviews

5.00
4 reviews

Average 5.00 out of 5 stars based on 4 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor

5 stars
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Don't miss out!
On average, this is booked 31 (0) days in advance.

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What's Included

Activity name

  • Entrance fee
  • Bottled water
  • Gratuities

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Wheelchair accessible
  • Transportation options are wheelchair accessible
  • All areas and surfaces are wheelchair accessible
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • This tour/activity will have a maximum of 15 travelers

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