Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

Thinking about stepping back into the roaring twenties, but with a modern twist? For just $48 per person, you can learn about Chicago’s clandestine drinking scene from the Prohibition era. Whether you prefer a downtown walking tour or a bus tour exploring neighborhoods like Lincoln Park and Wicker Park, both options promise a lively mix of history, architecture, and cocktails. Lasting around 3 to 4 hours, these tours are perfect for curious travelers eager to see the city through a different lens—one filled with gangsters, politicos, and secret speakeasies.

What we love about this experience? First, the expert guides like Jonathon, who bring the era to life with engaging storytelling and genuine passion. Second, the chance to visit authentic historic bars, some with stunning interiors and fascinating backstories. A possible consideration? The tour may involve some walking or bus rides in less-than-pleasant weather, so planning for rain or snow is wise. Overall, if you’re someone who appreciates history with a side of fun and enjoys a drink or two along the way, this tour will hit the spot.

This experience is perfect for history buffs, nightlife enthusiasts, or anyone curious about Chicago’s infamous past. Since the tours are adults-only and include adult themes, it’s most suitable for those over 21 who enjoy lively storytelling and a good cocktail.

Key Points

• Authentic Historic Venues: You visit 3 or 4 iconic speakeasies, each with its own unique story and atmosphere.
• Expert Guides: Guides like Jonathon are praised for their knowledge, storytelling style, and engaging personalities.
• Flexible Options: Choose between a downtown walking tour or a bus tour exploring neighborhoods outside the Loop.
• Adult Experience: No minors; expect adult themes and language, making it a lively, mature outing.
• Drinks for Purchase: You can buy drinks at each stop, with recommendations from your guide to match the era.
• Weather-Ready: Tours run rain, snow, or shine—so dress accordingly to enjoy every moment.

You can check availability for your dates here:

The Charm of Chicago’s Prohibition History

Stepping into this tour, we’re transported to a time when alcohol was illegal, yet everyone from gangsters to high society found ways to indulge. The allure lies in the secretive nature of speakeasies, hidden behind unassuming doors, and the stories behind them that our guides unravel with enthusiasm. This isn’t just a bar crawl; it’s a narrative about Chicago’s mobsters, politicians, and cultural shifts during the Prohibition years.

Many reviews highlight how guides like Jonathon add a layer of authenticity through storytelling that feels more like a lively chat than a lecture. As one reviewer puts it, “He has a nice storytelling way to tell about the prohibition in general but specifically in Chicago.” Expect to hear about notorious gangsters like Al Capone, hotels and bars that once hosted illegal bottles, and the social upheaval that led to Chicago’s reputation as a hub of booze and crime.

Itinerary Breakdown: What You’ll Actually See and Do

The Downtown Walking Tour Option

This option focuses on the Loop and River North areas, places with a dense concentration of historic venues. It’s less than a mile of walking, making it accessible, but still packed with small, fascinating stops. Here, you’ll get up-close views of some of Chicago’s iconic buildings, along with doorways that once hid speakeasies. The guide takes care to explain how alcohol flowed through Chicago’s streets, from the gangster hangouts to establishments that catered to the city’s elite, sometimes requiring fancy jackets for entry.

Reviews rave about how guides like Jonathon bring the past to life with photos, and some stops include access to legendary places like Harry Caray’s, adding a visual and tangible element to history. You’ll learn about the struggles and clever tricks used by bartenders and patrons to bypass the law, as well as how Chicago’s architecture played a role in hiding clandestine activities.

The Neighborhood Bus Tour

If you prefer to sit back and let the city come to you, the bus option is a solid choice. It covers four neighborhoods—Gold Coast, Lincoln Park, Wicker Park, and River North—each with their own history of speakeasies and celebrity hangouts. The bus visits historic establishments, some of which have kept their original charm, while others have been modernized into vibrant bars.

This tour is praised for its insightful commentary, with guides explaining the full scope of Prohibition’s impact on Chicago’s development. It’s a chance to see more of the city’s diverse neighborhoods—from posh districts to bohemian enclaves—all while comfortably enjoying the ride.

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The Speakeasies Itself: Atmosphere and Drinks

Each venue brings a different vibe—some are glamorous hotel bars, others are cozy, dimly lit hideouts. The guides often recommend drinks that reflect the era, such as classic cocktails like the Old Fashioned or Gin Rickey, which you can buy for a few dollars at each stop. Many reviews highlight that the drinks are available for purchase, but the true value lies in the ambiance and storytelling.

One reviewer notes, “We enjoyed the whole 3 hours very much and would definitely do it again. Highly recommend!!” Others appreciated how the venues preserve the old-time atmosphere with vintage decor, making you feel like you’ve stepped into a different era. Some stops even have beautiful interiors or historic significance, adding depth to your experience.

The Guides: The Heart of the Tour

Time and again, reviews praise the guides—particularly Jonathon—for their knowledge, humor, and approachable style. One reviewer states, “Jonathon was excellent as our guide. Super knowledgeable and enthusiastic about the subject matter.” He keeps the group engaged with fascinating stories, photos, and local insights. Some mention the language used—adult themes and adult language are part of the experience—so it’s clear this isn’t a family-friendly tour but a lively adult adventure.

Many travelers find that these guides make the history accessible and fun, transforming what might seem like a dry topic into a lively, memorable journey. Their passion for Chicago’s history shines through, making the experience more than just a visit to bars—it’s a storytelling journey into the city’s clandestine past.

Pricing and Value: What You’re Getting for $48

At $48, this tour offers great value considering it includes guidance, visits to multiple venues, and a deep dive into Chicago’s Prohibition past. When you consider the cost of drinks, transportation (if on the bus), and guided insight, it’s an efficient way to combine history, entertainment, and a taste of Chicago’s vibrant nightlife.

Some reviews suggest that adding drink specials could enhance the experience, especially given the ticket price, but most agree the storytelling and atmosphere justify the cost. It’s also flexible—cancel for free up to 24 hours in advance—so travelers can secure their spot with confidence.

This experience suits adults who enjoy history, storytelling, and a lively atmosphere. If you’re interested in mobsters, Prohibition antics, or Chicago’s hidden past, you’ll find plenty to love. It’s ideal for nightlife lovers, history buffs, or groups seeking a fun, educational outing. Those who prefer quiet, family-friendly tours might want to look elsewhere, but for a mature, engaging experience with a side of cocktails, this tour hits the mark.

For anyone wanting to combine Chicago’s vibrant history with a fun night out, this speakeasy tour offers a compelling mix. You’ll walk away with a deeper understanding of the city’s Prohibition years, along with some fantastic stories and drinks. The guides’ enthusiasm and the historic venues create a memorable experience that appeals to both history enthusiasts and nightlife explorers.

While it’s not a silent museum visit—expect adult themes, lively language, and spirited storytelling—it’s exactly this energy that makes it such a unique way to experience Chicago. Better yet, the small group size ensures a personal experience, and the flexible options mean you can tailor your adventure to your interests.

If you’re in Chicago and curious about the city’s illicit past, or simply looking for a fun, authentic evening out, this speakeasy tour is a top choice.

Is this tour suitable for minors?
No, the tour is for adults over 21 due to adult themes and language.

Can I buy drinks at the speakeasies?
Yes, drinks are available for purchase at each venue, with some recommendations from guides.

How long does the tour last?
It runs approximately 3 to 4 hours, usually in the afternoon.

What should I bring?
Bring a valid ID or passport, and cash or credit card to purchase drinks or tips.

Is the tour accessible if I have mobility issues?
The walking tour covers less than a mile, but some venues might have stairs or limited accessibility. The bus tour is more accommodating in that regard.

What’s the difference between the walking and bus options?
The walking tour offers a more intimate, close-up experience in downtown, while the bus tour covers larger neighborhoods comfortably from a seat.

Do I need to book in advance?
Yes, reservations are recommended. You can cancel free up to 24 hours in advance if plans change.

What if the weather’s bad?
The tours run rain, snow, or shine. Dress appropriately for the weather, especially if choosing the walking option.

Whether you’re a history nerd, a cocktail lover, or just looking for a memorable night out in Chicago, this Prohibition Speakeasies tour offers a well-balanced and engaging experience. Get ready to hear stories you never knew and visit hidden gems that make Chicago’s past come alive.

You can check availability for your dates here: