Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

Traveling through Chicago’s lively streets, you might stumble upon some intriguing corners of the city’s Prohibition history. This tour offers a chance to step back into an era when booze flowed clandestinely, and gangsters and high society mingled in secret.

Whether you prefer the intimacy of a walking tour in downtown or the comfort of a bus tour across neighborhoods, this experience delivers a fun, informative glimpse into Chicago’s spirited past.

What we love about this tour are the knowledgeable guides who weave stories with humor and authenticity, and the chance to visit iconic speakeasies that still exude the glamour and grit of the 1920s. A potential consideration is the adult-only nature of the tour, which might not suit travelers with children or those looking for family-friendly activities.

This experience is perfect for history buffs, curious travelers wanting to see Chicago through a different lens, or anyone keen on sampling classic cocktails while learning about the city’s notorious past. If you enjoy stories of gangsters, secret bars, and a lively atmosphere, this tour hits the right notes.

This experience made our article of Chicago’s 15 Top Walking Tours.

Key Points

• Two tour options: Downtown walking or neighborhood bus tour, catering to different preferences.
• Visit 3 or 4 speakeasies: Each with its own unique vibe and history.
• Learn about Chicago’s Prohibition past: From gangsters to high society, the stories are vivid and engaging.
• Enjoy adult beverages: With recommendations at each stop, you can indulge responsibly in period-appropriate drinks.
• Small group feel: Tours are capped at 20 people, making for a more personal experience.
• Ideal for adults: The tour includes adult themes and language, making it unsuitable for minors.

You can check availability for your dates here:

An In-Depth Look at the Experience

Choosing Your Style: Walking or Bus Tour

The experience offers two distinct ways to explore Chicago’s Prohibition past. The Hidden in Plain Sight Downtown Walking Tour takes you through Chicago’s Loop and River North, covering less than a mile but packed with stories and sights. If you prefer a more relaxed ride, the Original Chicago Prohibition Bus Tour whisks you across neighborhoods like Gold Coast, Lincoln Park, and Wicker Park, stopping at historic bars along the route.

Both options share core elements: stops at 3 or 4 speakeasies, insights into the era from your guide, and opportunities to buy adult drinks. The main difference lies in the pace and scenery—walking immerses you in the city’s streets, while the bus offers a broader view of neighborhoods.

The Stops and Their Significance

On the walking tour, you’ll get close-up looks at iconic establishments in downtown Chicago. These venues aren’t just bars—they’re portals to a time when booze was illegal, and everyone from gangsters to the city’s elite had secret spots to unwind. Reviewers have noted how the guide’s storytelling style brings these places alive, with some mentioning access to historic sites like Harry Caray’s premises.

The bus tour, meanwhile, explores a richer tapestry of Chicago’s neighborhoods. Visiting districts like Wicker Park and Lincoln Park, you’ll see how Prohibition influenced different parts of the city and visit establishments that retain the charm of the era. Travelers have appreciated the balanced mix of history and adult fun, as well as the opportunity to see neighborhoods they might not explore on their own.

The Guides and Their Role

Across reviews, the guides shine as the tour’s highlight. Described as knowledgeable, engaging, and personable, they have a knack for storytelling that makes history memorable. One reviewer exclaimed, “Jonathan was excellent—super knowledgeable and enthusiastic,” emphasizing how the guide’s passion elevates the experience.

The guides also help you navigate the adult themes and adult language—they keep the tone authentic without crossing into inappropriate territory. This makes the tour both educational and entertaining, with a few colorful stories along the way.

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The Speakeasies Themselves

Each stop is carefully chosen for its historical significance and ambiance. Expect to visit venues that range from hidden gems to luxurious hotels, all steeped in the Prohibition aesthetic. Reviewers mention the stunning interiors and great drinks, which are available for purchase at each location, with some guides providing recommendations for classic cocktails like gin rickeys or whiskey sours.

One traveler remarked, “The bars we visited had great drinks and fascinating history,” underscoring that this isn’t just a sightseeing tour but also a chance to indulge and experience the era firsthand.

Duration, Group Size, and Value

The tour lasts about 3 to 4 hours, making it an efficient way to experience Chicago’s Prohibition history without feeling rushed. With a maximum group size of 20, it maintains an intimate atmosphere, allowing plenty of opportunity for questions and interaction.

At $48 per person, the tour offers solid value—you’re not just paying for transportation and entry but for a memorable story-rich experience with expert guidance. When you consider the cost of individual drinks, the access to historic sites, and the knowledgeable narration, it’s clear that this tour provides good bang for your buck.

What the Reviews Say

Authentic feedback highlights consistently high praise. Many travelers emphasize the expertise and enthusiasm of the guides. One reviewer wrote, “Jonathan was super knowledgeable and enthusiastic,” while another appreciated the “dry humor and captivating storytelling.”

Multiple reviews mention how the tour brings Chicago’s history to life, with some noting special access to historic locations like Harry Caray’s premises. Drinks and tapas are mentioned positively, with visitors enjoying the relaxed, fun atmosphere.

Some critics pointed out that the adult language used by guides might not be suitable for everyone, but overall, the reviews strongly favor the informative and entertaining nature of the tour.

Practical Tips Based on Reviews

• Bring cash or credit cards for drinks and tips.
• Dress comfortably; walking is less than a mile if you choose the downtown tour.
• Prepare for rain or shine, as tours operate in all weather conditions.
• Remember that this is an adults-only experience—no minors allowed.
• If you’re a history buff or curious about Chicago’s gangster past, this tour will satisfy that curiosity with vivid stories and stunning venues.

Final Thoughts: Who’s This Tour For?

This tour is ideally suited for adults who enjoy stories of gangsters, secret bars, and a lively, authentic atmosphere. It’s perfect for those looking to combine a bit of history with a social experience—with drinks, good conversation, and lots of fascinating tales.

If you’re visiting Chicago and want a fun, engaging way to learn about the city’s Prohibition era without spending a fortune, this tour offers a great mix of entertainment and education. The small group format ensures a personalized feel, and the guides’ storytelling keeps things lively.

Travelers who value authentic venues and appreciate knowledgeable guides will find this experience worthwhile. However, if you prefer a more family-friendly or kid-oriented activity, this isn’t the right fit. It’s adult-oriented, spirited, and designed for those ready to embrace Chicago’s lively past.

FAQ

Is this tour suitable for children?
No, this is an adults-only tour due to adult themes and language, and participants must be 21 or older.

What’s included in the tour price?
You get access to 3 or 4 speakeasies, a professional guide (and driver if on the bus tour), and the stories that bring these places to life. Drinks are available for purchase.

Can I buy drinks at the speakeasies?
Yes, you can purchase adult beverages at each stop, with the guide providing recommendations on what to order.

How long does the tour last?
Expect it to run between 3 and 4 hours, usually in the afternoon.

Is the walking tour long or strenuous?
The downtown walking tour covers less than a mile, so it’s suitable for most fitness levels and requires only a light amount of walking.

What should I bring?
Bring your passport or ID, cash or credit card for drinks, and dress comfortably for the weather, as tours operate rain or shine.

To sum it up, this Chicago speakeasy tour offers a lively, well-informed peek into the city’s past. It’s a fantastic choice for those wanting to combine history, fun, and adult beverages in a friendly environment. Whether on foot or by bus, you’ll leave with a better understanding of Chicago’s notorious Prohibition days—and perhaps a great story or two to tell back home.

You can check availability for your dates here: More Great Tours Nearby