This was my second tour with Dave, and I look forward to whatever topic he presents next! His material, as always, was well researched, historically accurate, and engaging. He makes the past feel so visual and present. It was fun seeing how the mob and the law intersected across Chicago and how much Prohibition era shaped Jazz in Chicago. Also learned why Capone isn't the hero so many Chicago souvenirs portray him to be! It's a comprehensive tour; Dave covers history, culture, architecture, film, and movies from the Prohibition era. He shares fun trivia and even adds bonus context - a link to a curated playlist of the music and movie soundtracks discussed on the tour which he sends all participants the next day. Dave's tour is well paced and considerate of bathroom breaks! Five stars all around!!!
Prohibition Chicago: Myth vs. Reality Walking Tour
+3 photos
At a glance
- Duration
- 2 hours
- Price from
- $35 / person
- Rating
- 5.0 / 5 · 1 reviews
- Languages
- EN
- Group
- Small group, up to 15
- Cancellation
- Free cancellation
- Meeting point
- We'll meet in the plaza on Michigan Ave. between the Tribune Tower and the Apple Store. We'll talk about the first non-Indigenous people to come through the region and how it led to the birth and growth of Chicago.
- Confirmation
- Instant
Prices checked on Sep 11, 2026Things to do in Chicago
Description
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.
Tour Options
Itinerary
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.
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.
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.
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.
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.
Opened in 1897 as the city's first public library, the Chicago Cultural Center was used in two crucial scenes in "The Untouchables."
Highlights
Entrance fee
What's included
Included
Entrance fee
Not included
Gratuities
Bottled water
Traveller Ratings
5.0
1 reviews
Important Information
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Suitable for all physical fitness levels
Frequently asked questions
How long does Prohibition Chicago: Myth vs. Reality Walking Tour take?
Prohibition Chicago: Myth vs. Reality Walking Tour lasts about 2 hours. The itinerary has 6 stops.
How much does Prohibition Chicago: Myth vs. Reality Walking Tour cost?
Prices start at $35 per person for this Chicago experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
Can I cancel Prohibition Chicago: Myth vs. Reality Walking Tour for free?
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
Where does the tour start?
The meeting point is We'll meet in the plaza on Michigan Ave. between the Tribune Tower and the Apple Store. We'll talk about the first non-Indigenous people to come through the region and how it led to the birth and growth of Chicago.. Hotel pickup is not part of this experience.
What languages is Prohibition Chicago: Myth vs. Reality Walking Tour offered in?
The experience is available in EN.
Is this a private or a group tour?
It is a small-group experience with a maximum of 15 participants.
Is the tour suitable for children?
Infants and small children can ride in a pram or stroller
Is the tour wheelchair accessible?
Wheelchair accessible Transportation options are wheelchair accessible All areas and surfaces are wheelchair accessible
Reviews(1)
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More Chicago I never knew existed!
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