Private Speakeasy Pub Crawl in Chicago with Local Historian

A Closer Look at Chicago’s Secret Spirit of the 1920s

Imagine strolling through the streets of Chicago at night, stepping through secret entrances into hidden bars that once served gangsters like Al Capone and bootleggers during Prohibition. That’s exactly what this Private Speakeasy Pub Crawl offers: a chance to explore Chicago’s underground drinking scene with a knowledgeable local historian guiding you through history, stories, and authentic venues. The experience promises a fun, intimate night out that combines history, architecture, and craft cocktails — all in a private, customizable setting.

One of the biggest highlights we love is the personalized approach. With a private guide, you’ll get tailored insights and the chance to ask questions about Chicago’s notorious past. Plus, the inclusion of hotel pickup and drop-off makes logistics smooth, letting you focus solely on the fun. However, it’s worth noting that drinks are not included in the price, which can add up, especially if you’re planning to indulge in several prohibition-era cocktails.

This tour is perfect if you’re a history buff, a fan of craft cocktails, or someone looking for a unique night out that offers more than just another bar crawl. It’s also great if you want an intimate experience rather than a crowded group, and the option to dress up or wear period attire makes it even more memorable.

Key Points

• Private and personalized experience with a knowledgeable historian guide
• Visit authentic, historic speakeasies still operating today
• Includes luxury transportation with hotel pickup and drop-off
• Learn intriguing stories of Chicago’s gangster era and bootlegging
• Enjoy the ambiance of secret entrances and vintage decor
• Cost does not include drinks, so budget accordingly

The Detailed Experience: What to Expect

From the moment you book, this tour emphasizes the exclusivity and intimacy of a private experience. Priced at $101 per person for approximately three hours, it offers a comprehensive look into Chicago’s Prohibition-era nightlife. You’ll be picked up from your hotel in a luxury private vehicle, which takes away any worries about transportation and allows you to settle in comfortably. Being picked up and dropped off at your accommodation is a thoughtful touch, especially after a night of cocktails and stories.

The Itinerary: Inside Chicago’s Hidden Bars

Your journey begins with the guide, a professional historian, sharing insights into Chicago’s notorious gangster past. As you arrive at each venue, you’ll enter via secret entrances—something that adds a layer of thrill to the experience. Many of these bars are preserved in original condition, giving you a genuine glimpse of the 1920s atmosphere.

One of the key venues mentioned is The South-side, famously loved by Al Capone himself. Here, you might have the chance to order a prohibition-era cocktail — though drinks are purchased separately. The guide will recommend classic cocktails like the Mint Julep or the Sidecar, based on the history of what gangsters used to order, enhancing the feeling of stepping back in time.

Atmosphere and Decor

Expect vintage furnishings, period-specific decor, and a secretive ambiance that transports you to the era of gangsters, bootleggers, and speakeasies. Some venues might even have live jazz or blues, adding to that authentic 1920s vibe. If you choose to dress up in period clothing, it’ll only heighten the sense of being part of a bygone era, and reviewers mention that costumes rented from local shops can attract a lot of attention.

Stories and Insider Facts

What makes this tour particularly special are the stories the guide shares. From tales of racketeering to notorious Chicago gangsters, you’ll learn details you won’t find in a history book. Reviewers have appreciated guides like Conor and Stefan, who are praised for their wealth of knowledge and engaging storytelling. One reviewer pointed out that Stefan made “the whole experience very easy and memorable,” and another highlighted that their guide, Kai, knew “almost everything about the city.”

The Venues

While each stop varies, the focus remains on venues that have stood the test of time, often with original interiors. Besides The South-side, other bars in the area are still operating as speakeasies and retain their hidden entrances. This adds to the thrill, especially when entering through a disguised door or a nondescript alleyway.

The Value: Is It Worth the Price?

At $101, this private tour balances cost and experience well, especially considering the private transportation and tailored guidance. Reviewers mention that the tour skips long lines—a significant advantage in busy Chicago nightlife—and the private setting allows for more personalized interaction with the guide. While drinks are separately purchased, the guide’s recommendations for cocktails can enhance the experience, making each sip feel like a historic homage.

One reviewer found the price a bit steep, noting that at $330 per person, it might seem expensive without drinks included. However, considering the private transportation, personalized service, and exclusive access, many feel it offers solid value for a special night out.

Who Would Love This Tour?

This experience is perfect for history enthusiasts, anyone interested in Chicago’s gangster past, or those celebrating a special occasion like a bachelor/bachelorette party. It’s also suitable for travelers who prefer a more intimate, customized experience rather than a crowded bar crawl. The option to dress in period clothing adds a fun element for those wanting to go all out.

Final Thoughts: Who Is This Tour Best For?

If you’re looking for a unique, immersive journey into Chicago’s past, this speakeasy pub crawl is a fantastic choice. It provides a good blend of history, ambiance, and storytelling, making it more than just a night of drinking. The private aspect and hotel pickup make it especially appealing for travelers who want a hassle-free, personalized experience.

For those who love vintage decor, intriguing stories, and hidden bars, this tour delivers on all fronts. However, if budget is a concern and you prefer included drinks, you might want to consider whether this format matches your expectations. Still, many reviewers say the knowledgeable guides and authentic venues make it a memorable night worth the cost.

In summary, this tour caters well to those wanting an engaging, stylish, and historical night out in Chicago, with the convenience of private transportation and an expert guide leading the way.

Frequently Asked Questions

Is transportation included in the tour? Yes, the tour features luxury private transportation with hotel pickup and drop-off, making the experience seamless and comfortable.

Are drinks included in the tour price? No, the tour does not include drinks; they are available for purchase at each venue separately.

What is the dress code? The recommended dress code is smart casual. However, guests are encouraged to wear period costumes if they wish, adding to the fun and authenticity.

How long is the tour? The tour lasts approximately 3 hours, providing plenty of time to explore several venues and hear stories from your guide.

What is the minimum age for participants? The minimum age to participate is 21 years, aligning with legal drinking age requirements.

Can I cancel the tour? Yes, cancellations are free if made at least 24 hours in advance. Within 24 hours, the booking is non-refundable.

Is this tour suitable for all travelers? Most travelers can participate, but those with mobility issues should confirm accessibility details beforehand.

What kind of guides lead the tour? A professional historian guides the experience, offering detailed insights into Chicago’s gangster and speakeasy history.

Can I wear period clothing? Yes, you are welcome to wear period attire or fancy casual outfits to enhance the experience. Renting costumes from local shops is also an option.

Final Word

This Private Speakeasy Pub Crawl in Chicago offers an engaging blend of history, exclusivity, and fun. It’s well-suited for couples, groups celebrating special occasions, or solo travelers eager to uncover Chicago’s clandestine past. With knowledgeable guides, unique venues, and the option to dress up, it promises a memorable night that’s both educational and entertaining. Whether you’re a history buff or simply looking for a different kind of night out, this tour stands out for its authenticity and personalized touch.