Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Exploring Chicago’s Speakeasy Scene: A Closer Look at the Private VIP Tour

Imagine stepping back into the roaring 1920s, where Chicago’s streets buzzed with gangsters, bootleggers, and secret bars known as speakeasies. That’s exactly what this 3-hour private speakeasy cocktail VIP tour promises—an intimate, personalized journey into a time when Prohibition kept alcohol hidden but the nightlife thriving. If you’re a history buff or just someone curious about Chicago’s underground scenes, this tour could be a memorable addition to your visit.

What really caught our eye are the private group setting and the chance to visit historic venues through secret entrances—it’s like being part of a clandestine club. Plus, the fact that you’re chauffeured around in a luxury vehicle makes the experience feel exclusive and comfortable. On the flip side, one thing to keep in mind is that alcohol isn’t included, so you’ll need to be prepared to buy your drinks at each stop. This tour hits the sweet spot for those who love a mix of history, a touch of glamour, and a laid-back, private vibe—perfect for couples, friends, or small groups seeking a unique night out.

Key Points

• Private and personalized experience tailored to your group size and interests
• Historic speakeasies with original features and secret entrances
• Knowledgeable guides who share colorful stories about Chicago’s Prohibition era
• Luxury transportation for a comfortable, stylish ride around the city
• Flexible booking options with free cancellation up to 24 hours in advance
• Cost includes hotel pickup, drop-off, and chauffeur gratuity, with drinks available for purchase

You can check availability for your dates here:

Introduction to the Experience

If you’ve ever wondered what it was like during Chicago’s Prohibition era, this private speakeasy tour offers a taste of that clandestine nightlife. Though we haven’t taken this exact trip ourselves, what stands out is how it combines history with entertainment and a touch of luxury. It’s a chance to visit several venues that have been open since the 1920s, many of which look as if they’ve been frozen in time, preserving their original charm.

Two things we love about this tour are the expert guides—who are young local historians with a knack for storytelling—and the private group setup that ensures a relaxed, tailored experience. We also appreciate that transportation is luxury-grade, meaning you travel in style and comfort, not cramped buses or shared rides. However, a small consideration is that alcohol isn’t included, so you’ll want to budget for drinks at each speakeasy stop.

This experience would suit history enthusiasts, couples, friends, or small groups looking for a fun, immersive night out. It’s ideal for those who enjoy a mix of storytelling, discovering hidden venues, and sampling cocktails with a bit of historical flair.

What’s Included and What to Expect

This tour is designed to offer a comprehensive, immersive experience that balances history, ambiance, and comfort. Over three hours, you’ll visit three to four well-preserved Chicago speakeasies, each with its own character and secrets. Your guide, a passionate and knowledgeable local, will take you through secret entrances—think hidden doors and clandestine passages—that lead you into these historic venues.

As you arrive at each stop, your guide will share stories of the rampant racketeering, gangsters, and bootlegging that made 1920s Chicago infamous. Expect to hear about infamous figures and some of the colorful personalities behind the prohibition-lit scenes. The venues themselves often retain original features, giving you the feeling of stepping back in time.

Drinks are available for purchase at each stop—your guide will suggest kind of cocktails that gangsters or bank robbers might have ordered, adding an extra layer of authenticity and fun. It’s worth noting that the tour includes hotel pickup and drop-off within Chicago, so the transportation aspect is seamless, allowing you to relax and enjoy the ride without the hassle of navigating city streets.

The Journey Through Chicago’s Prohibition Era

First Stop: Historic Speakeasies

Your journey begins with entry into one of Chicago’s historic speakeasies, many of which have been lovingly preserved to look as they did nearly a century ago. These venues often feature vintage decor, dim lighting, and an ambiance that transports you back in time. The secret entrances add a fun, almost treasure-hunt element to the tour, as your guide leads you through concealed doors and hidden hallways.

More Great Tours Nearby

Second and Third Stops: Authentic and Atmospheric

The other venues are just as captivating, each with its own story and vibe. Some of these spots have served locals and famous gangsters for decades, and many are still operating as functioning bars. The preservation of original features means you can expect vintage fixtures, neon signs, and perhaps even old photographs on the walls. These settings make for great photo opportunities and memorable moments.

The Stories That Make It Special

What sets this tour apart is the narrative your guide provides. As one reviewer pointed out, guides like Kai are knewledgable and flexible, tailoring the experience based on what you’re interested in. Whether you want to hear more about the gangster legends or the day-to-day life in a speakeasy, your guide will pivot accordingly. As Maryann shared, “Alan, our host, was knowledgeable, kind and funny. He took us to great spots and made everything so fun.”

The Transportation and Comfort Factor

The luxury transportation is a definite highlight. Depending on your group size, you might be riding in a sleek Mercedes S 550 Sedan, a Cadillac Escalade, or a Mini Coach Bus—whichever fits your group comfortably. This isn’t just about style; it’s also practical, ensuring you’re not navigating unfamiliar streets after a few drinks. The hotel pickup and drop-off make it convenient, especially if you’re staying downtown or close to the city center.

The tour’s duration of three hours strikes a good balance—enough time to visit multiple venues, listen to stories, and enjoy a couple of drinks without it dragging on too long. Plus, the fact that you can cancel up to 24 hours in advance for a full refund adds a nice layer of flexibility, especially if your plans are still a bit fluid.

Price and Value

At $950 per group of up to five people, this tour is certainly on the higher end, but considering the private setting, luxury transport, and personalized experience, it offers good value—especially for a special night out. The experience isn’t just about the drinks, but about accessing historic venues that are otherwise hard to visit and listening to compelling stories from a guide who knows the city inside out.

Keep in mind: alcohol isn’t included. You’ll purchase your drinks, which can add to the overall cost, but also gives you the freedom to choose what you want to sip. The tour’s private nature and inclusion of hotel pickup and drop-off mean you’re paying for comfort, exclusivity, and a curated experience.

Who Will Love This Tour

This experience is particularly well-suited for adults who enjoy history, storytelling, and boutique experiences. It’s ideal for small groups or couples looking for a unique, intimate night out. If you’re a fan of Chicago’s gangster lore or vintage aesthetics, this tour will speak to you. It’s also great for those who prefer private, flexible tours over crowded group excursions.

However, it’s not suitable for people with mobility impairments or anyone under 21, as alcohol consumption is involved and some venues may have stairs or uneven flooring.

Final Thoughts

For anyone wanting to explore Chicago’s Prohibition past in a personal, stylish, and relaxed way, this private speakeasy tour checks a lot of boxes. The combination of expert guides, secret entrances, and luxury transportation makes it stand out from typical bar-hopping or group tours. It’s a great way to get a behind-the-scenes look at a fascinating era, all while enjoying a night out in comfort.

If you’re looking for a well-organized, engaging, and exclusive experience that balances storytelling with fun, this tour is definitely worth considering. It’s especially good for those who value quality over quantity and enjoy a bit of history with their cocktails.

FAQ

Is this tour private?
Yes, it’s designed for private groups of up to five people, making it a personalized experience.

Are drinks included?
No, alcoholic beverages are available for purchase at each speakeasy. The tour includes recommendations and stories about the drinks ordered during Prohibition.

What is the duration of the tour?
It lasts approximately 3 hours, including hotel pickup and drop-off.

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

Is there a minimum age requirement?
Yes, the tour is not suitable for travelers under 21 years old.

Can I cancel the tour?
Yes, you can cancel free of charge up to 24 hours before the scheduled start.

What should I bring?
Bring your ID or passport and driver’s license. Sleeveless shirts are not allowed.

Is the tour accessible for people with mobility issues?
No, this tour isn’t suitable for those with mobility impairments.

Are there guides who speak Chinese?
Yes, the tour offers English and Chinese language guides.

In the end, if you’re after an engaging, history-rich night in Chicago with a touch of luxury, this private speakeasy tour offers a well-crafted experience that balances storytelling, style, and exclusivity. It’s not just about drinking; it’s about stepping into a hidden world that once thrived in the shadows of the city.

You can check availability for your dates here: