Chicago Haunts and Hooligans Tour

The Chicago Haunts and Hooligans Tour takes visitors on a thrilling journey through the city’s Prohibition-era past. Guided by a local dressed in authentic 1920s attire, participants uncover the stories of notorious gangsters like Al Capone and "Bugs" Moran as they visit iconic bars that once fueled the bootlegging industry. With a small, intimate group, this unique experience combines history, mystery, and a lively Roaring 20s atmosphere, making it a must-do for those aged 21 and older. But what secrets do these haunted pubs still hold?

Key Points

• Immersive tour exploring Chicago’s Prohibition Era with stories about notorious gangsters like Al Capone and "Bugs" Moran.
• Guided walk visiting 3-4 historic bars and speakeasies linked to the city’s underground economy during the 1920s.
• Small group experience with a local guide dressed in Roaring 20s attire to enhance the historical ambiance.
• Opportunity to purchase alcoholic drinks while learning about Chicago’s bootleggers and mobsters.
• Moderate physical fitness required, tour operates in all weather conditions, and guests should dress appropriately.

Tour Overview

The Chicago Haunts and Hooligans Tour offers a unique exploration of the city’s Prohibition Era, boasting 19 reviews and a 100% recommendation from travelers.

This guided tour takes guests to 3-4 bars linked to notorious gangsters, where they’ll hear scary stories about bootleggers and mobsters.

Led by a local guide in Roaring 20s costume, the small group experience is ideal for friends seeking an alternative night out.

Priced from $34.77 per person, the tour is accessible to those 21 and older, and operates in all weather conditions, with free cancellation up to 24 hours in advance.

Experience Details

On the Chicago Haunts and Hooligans Tour, guests can explore Chicago’s Prohibition Era by visiting 3-4 bars linked to notorious gangsters.

They’ll hear scary stories about bootleggers and mobsters who roamed the city during this notorious time. The tour is ideal for friends seeking an alternative night out, with a local guide dressed in Roaring 20s costume leading the small group experience of no more than 14 travelers.

Alcoholic drinks are available for purchase, though gratuities aren’t included. Moderate physical fitness is required, and the tour operates in all weather conditions, so guests should dress appropriately.

Guided Tour Information

A local guide in Roaring 20s costume leads the small group experience, which has a maximum of 14 travelers. Alcoholic drinks are available for purchase during the tour. Gratuities are not included.

Guided Tour Information
Local Guide	Small Group	Alcoholic Drinks
Roaring 20s Costume	Max 14 Travelers	Gratuities Not Included

This atmospheric tour provides an immersive journey into Chicago’s Prohibition Era, exploring bars linked to notorious gangsters and uncovering their chilling stories.

Meeting and Ending Point

Travelers meet at Harry Caray’s Italian Steakhouse, located at 33 W Kinzie St in Chicago, IL 60654.

This is the starting point for the Chicago Haunts and Hooligans Tour. The tour ends back at the same meeting location.

Participants will explore Chicago’s Prohibition Era haunts linked to notorious gangsters and bootleggers. The tour lasts approximately 2-3 hours.

At the conclusion, travelers are free to continue their evening at their own pace, perhaps exploring more of the city’s historical watering holes.

Prohibition Era Gangsters

During the Prohibition Era, Chicago was a hotbed of illegal activity, with notorious gangsters and bootleggers controlling the city’s lucrative underground economy.

Some of the most infamous figures of the time included:

• Al Capone, the ruthless mob boss who built a criminal empire through bootlegging, extortion, and violent turf wars
• "Bugs" Moran, Capone’s longtime rival and leader of the North Side Gang
• "Diamond" Joe Esposito, a bootlegger and nightclub owner with links to the mafia

These larger-than-life characters and their lawless exploits continue to captivate the public’s imagination about Chicago’s tumultuous past.

Haunted Pubs and Bars

The Chicago Haunts and Hooligans Tour takes guests on a captivating journey through the city’s haunted pubs and bars with ties to notorious Prohibition-era gangsters.

Visitors will explore 3-4 watering holes linked to the bootleggers and mobsters who once roamed the city’s streets.

Along the way, a local guide in Roaring 20s costume shares chilling tales of the speakeasies and their sinister histories.

The small-group experience offers an alternative night out for friends seeking a thrilling glimpse into Chicago’s dark past.

Alcoholic drinks are available for purchase, though gratuities aren’t included.

Roaring 20s Atmosphere

A local guide in authentic Roaring 20s attire leads the Chicago Haunts and Hooligans Tour, instantly transporting guests back to the Prohibition era.

The small group experience features:

• Immersive storytelling about notorious gangsters and bootleggers
• Visits to 3-4 bars with direct ties to the city’s Prohibition past
• An opportunity to sip cocktails in a speakeasy-like atmosphere

The guided tour offers an alternative night out, blending history, horror, and the lively spirit of the Roaring 20s.

Travelers seeking an offbeat adventure will find the Chicago Haunts and Hooligans Tour a thrilling excursion.

Planning Your Visit

When planning your visit, guests will want to arrive at the meeting point, Harry Caray’s Italian Steakhouse, located at 33 W Kinzie St in Chicago, at least 15 minutes before the scheduled tour start time.

The small group tour has a maximum of 14 travelers and operates in all weather conditions, so dressing appropriately is recommended. Alcoholic drinks are available for purchase during the tour. Gratuities aren’t included, so guests should plan accordingly.

Confirmation is received at booking, and a moderate level of physical fitness is required. The tour offers free cancellation up to 24 hours in advance, and a "Reserve Now and Pay Later" option is available.

Frequently Asked Questions

Is the Tour Wheelchair Accessible?

The tour is not wheelchair accessible. The additional information clearly states that the tour "is not wheelchair accessible".

Can the Tour Be Customized for Private Groups?

The tour can be customized for private groups. However, it’s not wheelchair accessible. Customers should contact the tour operator to discuss any special requests or accessibility needs for their group.

What Is the Dress Code for the Tour?

The tour doesn’t have a strict dress code, but it’s recommended to dress comfortably and appropriately for the weather, as the tour operates in all conditions. Travelers are advised to dress in casual attire.

Are Children Allowed on the Tour?

The tour has a minimum age requirement of 21 years old, so children are not allowed to participate. The experience is intended for adult travelers seeking an alternative night out in Chicago.

Can I Bring My Own Alcoholic Beverages?

No, guests can’t bring their own alcoholic beverages. The tour allows for the purchase of alcoholic drinks at the 3-4 bars visited, but outside alcohol isn’t permitted as part of the guided experience.

Sum Up

The Chicago Haunts and Hooligans Tour offers a captivating journey into the city’s Prohibition-era past. Visitors enjoy the thrilling tales of notorious gangsters, while exploring historic bars and savoring the lively Roaring 20s atmosphere. This unique experience combines history, haunted stories, and a touch of 1920s nostalgia, making it a must-do for anyone aged 21 and above visiting Chicago.