Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

Exploring Chicago’s Prohibition Speakeasies: A Guide to the Best Tours

If you’re visiting Chicago and have a penchant for history, nightlife, or just good stories, a Prohibition Speakeasies tour offers a fascinating glimpse into the city’s secretive, illicit past. Whether you prefer to walk through downtown streets or hop on a bus to explore neighborhoods, these tours promise to transport you back to the roaring twenties, when Chicago was alive with gangsters, politicians, and clandestine bars.

What we find especially appealing about these tours is how they balance storytelling with authentic visits to some of the city’s most iconic speakeasies. Plus, they come with the fun bonus of offering drink recommendations so you can experience a taste of the era firsthand. A possible concern might be that the tours are primarily adult-themed, with adult language and themes, which isn’t suitable for under-21 travelers.

This experience is ideal for history buffs, nightlife enthusiasts, or anyone curious about Chicago’s notorious past. If you love immersive, guided stories with a mix of walking and drinking, this tour could be a highlight of your visit.

Key Points

• Choice of Experience: Select between an engaging Downtown walking tour or a comprehensive neighborhood bus tour.
• Authentic Visits: Explore 3 or 4 historic speakeasies known for their ties to Prohibition-era crime and high society.
• Expert Guides: Knowledgeable guides, like Jonathan, deliver entertaining and well-researched stories that bring the era to life.
• Flexible Duration: Tours last around 3 to 4 hours, fitting well into a day of sightseeing.
• Adult Focus: These are adults-only tours with adult themes and language.
• Value for Money: For around $48, you receive a guided experience with entry to multiple iconic bars and insightful commentary.

The Itinerary: What You Can Expect

Choosing your experience largely depends on your style. The Downtown Walking Tour, called Hidden in Plain Sight, is perfect if you want an intimate, close-up exploration of Chicago’s streets. It covers less than a mile but offers plenty of historical stories about how alcohol flowed through the city’s alleyways and upscale establishments during Prohibition. With a small group, you’ll visit three iconic speakeasies in the Loop and River North neighborhoods, places that once served gangsters like Al Capone and high-society Chicagoans.

On the other hand, the bus tour takes you on a broader journey through neighborhoods like Lincoln Park, Wicker Park, and the Gold Coast. It’s ideal if you want to see more of the city’s historic districts and learn about the full scope of Prohibition’s impact beyond just downtown. Visiting four different speakeasies, the guide shares stories of Chicago’s criminal underworld alongside the city’s elite, making for an engaging mix of history and modern-day bar culture.

What makes each stop special? Many of these venues are historic establishments with their own unique stories—some are beautifully restored hotels, others are tucked-away bars with decades of secrets. Reviewers have raved about how guides like Jonathan make the stories come alive, weaving humor, detailed facts, and personal anecdotes that keep everyone engaged.

Expect to purchase drinks at each speakeasy—recommendations are provided, so you get a sense of what the era’s authentic cocktails would have been. With prices varying, the experience offers good value, especially considering the number of locations visited and the insight gained.

Authentic Experiences at Historic Speakeasies

Each speakeasy has its charm and history. Some might have been frequented by gangsters, while others catered to Chicago’s high society. Many of the venues are stunning in their architecture and ambiance, often featuring vintage decor and dim lighting to evoke the era. As one reviewer pointed out, “The places he took us were superb,” and the bars themselves could be considered part of the tour’s appeal.

The guides are a highlight. One reviewer describes Jonathan as “a very smart and well-versed guide,” who makes the stories accessible and fun. This is crucial, as the history of Prohibition is complex, often filled with colorful characters and dramatic events. You’ll learn about the “how” and “why” behind Chicago’s infamous reputation, but also enjoy the lighter side—like the secret language, hidden entrances, and clever disguises used to keep the booze flowing.

The small group size (no larger than 20 people) ensures a more personal experience. Reviewers appreciated how guides, especially Jonathan, kept the atmosphere lively, answered questions, and encouraged interaction. Whether you’re traveling solo or with a group, this intimacy makes it easier to connect and absorb the stories.

Price, Duration, and Overall Value

At $48 per person, this tour offers significant value considering the number of locations, the storytelling, and the access to historic venues. For the price, you get a professional guide, entry to 3 or 4 speakeasies, and the chance to learn about a fascinating period in Chicago’s history.

The duration of around 3 to 4 hours is reasonable, providing a good balance of sightseeing, storytelling, and socializing. Whether you opt for the walking or bus version, you’ll find that the pacing is well-managed, keeping everyone engaged without feeling rushed.

While there’s no included food or drink, the opportunity to purchase cocktails or mocktails at each stop adds a fun touch. Reviewers frequently mention how guides give suggestions for drinks that represent the era—making the experience feel authentic and immersive.

Note: The tours run rain or shine, and group sizes are intentionally kept small for intimacy and safety. You’ll need to bring cash or cards for additional purchases and ID to verify your age, as these are adult-only tours.

Why This Tour Works Well

Many reviewers have praised the knowledgeable guides and the engaging storytelling. For example, one said, “Jonathan was funny and very informative,” adding that he “knew the prohibition events very well.” Others lauded the way the venues were carefully selected—not just for their historic importance but for their ambiance and storytelling potential.

The tour isn’t just about seeing bars; it’s about understanding how Chicago’s past shaped its reputation as a city of gangsters and secret societies. For those interested in history with a lively twist, this tour hits the mark.

The small group size and personalized approach mean you can ask questions freely and get more nuanced details, which broadens your understanding of the era beyond surface stories.

Who Should Consider This Experience?

This tour is perfect if you enjoy history, architecture, or nightlife and prefer a casual, engaging way to learn about Chicago’s Prohibition days. It’s especially suited for adults and those comfortable with adult themes and language.

If you’re a solo traveler, couple, or small group looking for a fun mix of storytelling, sightseeing, and drinks, this experience will likely be a highlight. It’s also a good choice for visitors who want a more authentic, behind-the-scenes look at historic Chicago bars that are often missed by travelers.

The Sum Up

The Chicago Prohibition Speakeasies tour offers an insightful, entertaining window into the city’s clandestine past. With knowledgeable guides, visits to iconic historic bars, and options for walking or bus travel, it provides flexibility for different preferences. The experience balances storytelling with opportunities to purchase authentic era-inspired drinks, offering real value for the price.

If you’re curious about the stories behind Chicago’s gangster legends, enjoy exploring vintage venues, or just want an engaging way to spend a few hours, this tour checks all the boxes. It’s a fun, educational, and surprisingly immersive look at a colorful chapter of Chicago’s history.

FAQ

Is this tour suitable for minors?
No, this tour is adults-only due to adult themes, language, and drinking.

How long does the tour last?
The tour generally runs for 3 to 4 hours, depending on the option chosen and group pace.

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

What’s included in the tour?
Entry to 3 or 4 speakeasies, a professional guide (and driver for the bus tour), and the experience of learning about Chicago’s Prohibition era.

Are there any dress codes?
No specific dress code, but comfortable shoes are recommended since walking or bus travel is involved.

Is this a walking or bus tour?
You can choose between a Downtown walking tour or a neighborhood bus tour, depending on your preference.

What should I bring?
Bring ID, cash or credit card for additional purchases, and weather-appropriate clothing.

What is the group size?
Tour groups are limited to 20 people for a more personal experience.

How do I book?
Reservations can be made online; tours are flexible, with options to reserve now and pay later.

What if I need to cancel?
Cancellations are free if made 24 hours in advance, offering flexibility if your plans change.