Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Looking for a unique way to explore Chicago’s lively past? This private Speakeasy Cocktail VIP Tour offers just that—a chance to step into the secret world of the 1920s, when Chicago’s underground bars buzzed with gangsters, bootleggers, and glittering jazz. It’s a guided journey through some of the city’s most storied venues, with a focus on history, atmosphere, and cocktails that once fueled Chicago’s notorious nightlife.

Two things stand out immediately—first, the thrill of entering hidden speakeasies via secret doors feels like being part of a clandestine club. Second, the tour’s storytelling is engaging, delivered by a youthful local historian who knows how to spin a good tale. The downside? The price tag is hefty at $950 per group, which might seem steep at first glance. But if you’re a history buff, a cocktail enthusiast, or simply after a memorable, private experience, this tour could be worth every penny. It’s best suited for small groups who crave intimacy, storytelling, and a taste of Chicago’s Prohibition-era glamour.

Key Points

• Private, customizable experience with a dedicated local guide
• Access to historic speakeasies through secret passages
• Authentic cocktails inspired by the era, available for purchase
• Transportation in luxury vehicles for comfort and style
• A focus on storytelling and historical context
• Suitable for groups up to 5 people, ages 21 and over

Exploring Chicago’s Prohibition Hidden Gems

The essence of this tour is about more than just drinks; it’s about reliving the secret, rebellious spirit of 1920s Chicago. The tour takes you through three to four working speakeasies, many of which have preserved their original charm—think vintage decor, low lighting, and an air of mystery. Your guide, a young local historian, will lead you through secret entrances and hidden passages, giving you a sense of what it was like to slip into a clandestine bar in the roaring twenties.

One of the most compelling aspects, as noted by previous participants, is the colorful storytelling. You’ll hear about gangsters like Al Capone, bank robbers, and the city’s racketeering scene—stories that bring the past vividly to life. Many reviews highlight that the guides are well-versed, making the experience both entertaining and educational. As one reviewer noted, “We loved the way the guide brought Chicago’s history alive with stories of racketeering and bootlegging, all set to a backdrop of vintage cocktails.”

The ambiance at each stop is carefully maintained, with many venues still in their original condition, adding authenticity to the experience. You’ll have the opportunity to purchase cocktails that might have been ordered by Chicago’s infamous gangsters—this isn’t just about drinking; it’s about tasting a slice of history.

What the Tour Includes and Why It Matters

The tour includes hotel pickup and drop-off within Chicago, making it hassle-free and adding an element of luxury. You’ll travel comfortably in a vehicle ranging from a Mercedes S 550 Sedan to a Mini Coach Bus, depending on your group size. This means no worries about navigating city streets or finding transportation between venues. It also enhances the sense of exclusivity.

For three hours, your guide provides an insider’s perspective on Chicago’s Prohibition era, mixing historical facts with lively storytelling. The tour’s focus is on authentic speakeasies, many of which have been open since the 1920s or meticulously restored. You get to experience as close as possible the clandestine nightlife of almost a century ago.

Regarding beverages, alcohol isn’t included in the price, but you’ll be encouraged to purchase cocktails at each stop. Your guide will suggest drinks that fit the era, adding a flavor of authenticity. Keep in mind that the tour is not suitable for under-21s and those with mobility issues, due to the nature of the venues and transportation involved.

The guide’s expertise and the private setting mean the experience is tailored to your group, making it a more personalized and relaxed way to learn about a fascinating chapter of Chicago history.

A Step-by-Step Look at the Itinerary

Start with a pickup at your hotel or designated location within Chicago city limits. From there, you’ll be chauffeured in a luxurious vehicle, setting a tone of sophistication and comfort. The first stop might be one of Chicago’s historic speakeasies, accessed via a secret entrance that transports you back to the 1920s.

Once inside, you’ll be greeted by vintage decor—think dark wood panels, subdued lighting, and jazz-infused ambiance. Your guide will share stories of how these venues operated during Prohibition, many of which are still functioning businesses. Expect to hear tales of gangsters like Al Capone, bootlegging, and city racketeering that kept Chicago’s underworld bustling.

Across the next stops, you’ll explore different venues, each with its own unique charm and history. Some venues might have original furnishings and decor, providing an immersive experience. The guide might recommend specific cocktails—probably classics like gin rickeys or whiskey sours—and tell you about the drinks ordered by notorious gangsters.

The tour concludes with a drop-off back at your hotel. Throughout, you’ll have had the chance to enjoy four or more speakeasies, each offering a different glimpse into Chicago’s secretive past.

Authenticity and Experience Based on Reviews

Six reviews give this tour a perfect 5-star rating, reflecting broad satisfaction. Participants consistently praise the knowledge and enthusiasm of the guide, with one saying, “The stories really brought the city’s past to life.” Others mention the authentic decor and the thrill of secret entrances—”It felt like being an insider,” one review states.

Several reviewers note the value of the private experience, making it ideal for couples, small groups of friends, or history enthusiasts. While the cost is above average for a city tour, many feel the personalized attention, exclusive access, and high-quality transportation justify the price.

Some comments indicate that the cocktail options are worth exploring, and it’s fun to see how the drinks reflect the era’s style. The tour’s focus on storytelling creates a lively, engaging atmosphere that leaves participants with a deeper appreciation of Chicago’s colorful past.

Why This Tour Is a Great Choice

This private speakeasy tour offers a unique blend of history, culture, and leisure. It’s ideal for those who want an intimate, tailored experience that combines storytelling with the thrill of secret doors and vintage cocktails. The three-hour duration strikes a good balance—long enough to soak in the atmosphere without feeling rushed.

It’s particularly good for history buffs, cocktail lovers, or anyone interested in Chicago’s underworld tales. The luxury transportation adds a touch of class, making it suitable for a special occasion or a memorable night out. Since the experience is private, you won’t be lost in a large crowd; instead, you’ll have the guide’s full attention.

However, travelers should note that the price might be steep for some, and the tour isn’t designed for those with mobility issues or under 21. But for those who can indulge, it promises an evening packed with stories, style, and secrets that have lasted nearly a century.

Final Thoughts

This Chicago Private Speakeasy Cocktail VIP Tour offers a rare opportunity to experience the city’s underground nightlife with an expert guide in a private setting. Its combination of authentic venues, engaging storytelling, and luxurious transport makes it stand out for those looking for a sophisticated, immersive experience.

While the cost may seem high, the personalized nature and access to historic speakeasies justify the expense for many. It’s perfect for couples celebrating something special, small groups of friends, or anyone eager to learn about Chicago’s notorious Prohibition era in style.

If you’re after a memorable, insider experience that blends history, glamour, and a bit of mischief, this tour delivers exactly that—rich stories, vintage vibes, and a night to remember.

FAQ

Is this tour suitable for people with mobility issues?
No, because the venues and transportation may not be accessible for those with mobility impairments.

Can I purchase drinks during the tour?
Yes, alcoholic beverages are available for purchase at each speakeasy stop, but they are not included in the tour price.

What is the minimum age requirement?
You must be 21 or older to participate, as alcohol is involved.

How long does the tour last?
The tour lasts approximately three hours, with checkable starting times depending on availability.

What transportation is used?
Depending on group size, you’ll be chauffeured in a luxury vehicle like a Mercedes S 550 Sedan, Cadillac Escalade, Mercedes Sprinter, or Mini Coach Bus.

Is the tour private?
Yes, it’s designed for your private group, up to five people.

What should I bring?
Bring a passport or ID card, and a driver’s license for verification.

Can I cancel?
Yes, you can cancel up to 24 hours in advance for a full refund.

How is the tour culturally immersive?
It combines historical stories with authentic venues and vintage cocktails, giving a true taste of Chicago’s Prohibition nightlife.

This private speakeasy tour is a fantastic way to combine history, craft cocktails, and a touch of adventure. For those interested in Chicago’s hidden past and craving a unique experience, it promises a night full of stories, style, and a little secretive fun.