Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

Exploring Chicago’s Prohibition history becomes a lively adventure with the Prohibition Speakeasies Bus or Walking Tour. For $48 per person, the tour offers a compelling mix of storytelling, historic venues, and the chance to sample period-appropriate drinks over 3 to 4 hours. Whether you prefer strolling through downtown or riding in a classic bus through neighborhoods like Gold Coast, Lincoln Park, Wicker Park, and River North, this tour immerses you in the city’s lively 1920s underground scene.

This experience is ideal for adults interested in history, architecture, or cocktail culture, and it garners a stunning overall rating of 4.9 out of 5 based on 130 reviews. Keep in mind that food and drinks are available for purchase, but are not included in the ticket price. The tour’s intimate size, limited to 20 participants, ensures a personal and engaging exploration of Chicago’s clandestine speakeasies.

Key Points

• Price and duration: Only $48 per person for a 3 to 4-hour experience, operating rain or shine.
• Tour options: Choose between a Downtown walking tour or a neighborhood bus tour.
• Highlights: Visit 3 or 4 historic speakeasies and learn about gangsters, politicians, and high society during Prohibition.
• Expert guides: Guides like Jonathan are praised for their knowledgeable, engaging storytelling and entertaining style.
• Drinks for purchase: Enjoy recommendations for period-appropriate drinks at each stop, with options to purchase cocktails or beverages.
• Limited group size: Tours are capped at 20 guests, fostering a more personal experience.

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Exploring Chicago’s Speakeasy Culture in the Loop and River North

The Downtown walking tour, called Hidden in Plain Sight, concentrates on the Loop and River North neighborhoods. Here, the guide takes you close to Chicago’s gangster hangouts, elite establishments, and hidden bars that served alcohol during Prohibition. The walk less than 1 mile makes it accessible for most, with plenty of opportunities to absorb the city’s clandestine past.

In contrast, the Original Chicago Prohibition Bus Tour visits 4 neighborhoods: Gold Coast Historic District, Lincoln Park, Wicker Park, and River North. This option covers more ground, with the bus transporting guests from venue to venue, offering a broader view of the city’s diverse districts. The bus also features a professional driver, adding comfort and convenience for those who prefer transportation.

Visiting Iconic Speakeasies and Historic Bars

Guests will visit 3 or 4 historic speakeasies depending on the tour choice. These venues are renowned for their authentic ambiance and connection to Chicago’s gangster past. Some venues are notable for their beautiful hotel settings or unique architecture, which is highlighted during the tour.

Many stops offer special drink recommendations that reflect the era’s signature cocktails. While food and drinks are not included in the ticket price, the venues provide ample options for purchase, allowing participants to enjoy period-inspired cocktails as they learn about the significance of alcohol during Prohibition.

The Guides: Storytelling, Knowledge, and Engagement

The tour guides, including the highly praised Jonathan, excel at delivering entertaining, detailed narratives about Chicago’s gangster scene and Prohibition history. Their ability to blend fun facts, historical context, and lively storytelling makes the experience captivating.

Many reviews highlight Jonathan’s expertise, approachable demeanor, and ability to keep the group engaged. Some note occasional use of foul language, but overall, the guides are seen as knowledgeable and charismatic, making the tour enjoyable for adults who appreciate a lively, storytelling style.

Logistics: Meeting Points, Group Size, and Accessibility

The meeting point varies depending on the chosen option but is clearly communicated. The group size is capped at 20 people, ensuring plenty of interaction and fewer crowds at each venue. The walking tour covers less than 1 mile, suitable for most mobility levels.

For the bus tour, a professional driver operates the vehicle, providing a comfortable ride between stops. The tour operates rain, snow, or shine, so dressing appropriately for weather is advised. Participants are reminded to bring passport or ID and cash for drink purchases.

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The Value and Overall Experience

At $48 per person, the tour offers excellent value considering the number of venues visited, the inclusion of a professional guide, and the focus on historic Chicago bars. The small group size enhances the experience, allowing for more personalized storytelling and interaction.

While food and drinks are extra, the recommendations at each speakeasy make it easy to indulge in authentic cocktails, adding to the immersive feel. The length of 3 to 4 hours tends to be well-paced, with some reviews noting the storytelling style makes the time fly by.

Comparing the Walking and Bus Options

Choosing between the Hidden in Plain Sight walking tour and the original bus tour depends on your preferences. The walking tour offers a more intimate experience along the city streets, with close-up views of historic landmarks. The bus tour covers more neighborhoods and provides a wider perspective on Chicago’s Prohibition-era hotspots.

Both options receive high praise for their guides and venue selections. The bus tour may appeal to those who prefer transportation convenience or want to explore more districts in less time. The walking tour suits those who enjoy more detailed exploration on foot.

Final Thoughts on the Chicago Prohibition Speakeasies Tour

This tour combines history, architecture, and adult entertainment in a way that entertains and educates. The expert guides, especially Jonathan, make the stories come alive, and the venues chosen are fascinating glimpses into Chicago’s past.

The $48 price point makes it an accessible way to experience Chicago’s underground nightlife and the city’s gangster legends. The small group size and personalized storytelling stand out, ensuring a more engaging experience than larger tours.

While the difference in stops and pace between walking and bus options** allows for personal preference, both are highly rated and deliver a memorable journey through Prohibition Chicago.

Frequently Asked Questions

Is the tour suitable for all ages?
No, these tours are adults-only, including adult themes and language, and are restricted to guests 21 and over.

What should I bring?
Participants should bring passport or ID card and cash for drinks or food purchased at the venues.

Can I cancel the tour?
Yes, free cancellation is available up to 24 hours in advance for a full refund.

Are food and drinks included?
No, food and drinks are not included but are available for purchase at each venue.

What if it rains or snows?
The tour operates rain, snow, or shine, so dress appropriately for the weather.

How long does the tour last?
The experience lasts between 3 and 4 hours, typically in the afternoon.

Is the walking tour accessible?
Yes, the walking segment is less than 1 mile, making it suitable for most participants.

What makes this tour different from other Chicago attractions?
This tour emphasizes the underground speakeasy culture, gangster stories, and historic bars, providing a unique blend of education and adult entertainment unavailable in standard city tours.

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