Private Speakeasy Pub Crawl in Chicago With Local Historian

Discover Chicago’s captivating Prohibition-era past on a private speakeasy pub crawl led by a local historian. You’ll uncover hidden bars with unmarked doors and authentic 1920s decor, sipping cocktails and listening to jazz as your guide shares fascinating stories of bootlegging and racketeering. This exclusive evening tour promises an unforgettable adventure steeped in history and intrigue. What secrets from the city’s vibrant past will you uncover?

This experience made our article of 8 Top Drinking Tours In Chicago (With Reviews & Prices).

Key Points

• Private evening pub crawl led by a professional historian that offers glimpses into the clandestine world of 1920s Chicago speakeasies.
• Immersive experience with unmarked doors, authentic decor, and captivating stories of bootlegging operations and power struggles during the Prohibition era.
• Encouragement of smart casual attire reminiscent of the 1920s to enhance the historical ambiance, with costumes not required but adding to the adventure.
• Luxury private transportation for comfort and convenience, with pickup available from hotels or venues within the Chicagoland area.
• Knowledgeable tour guides, such as Conor and Kai, who provide a wealth of expertise and dynamic presentations on Chicago’s bootlegging history.

Exploring Chicago’s Speakeasies

Although Chicago is known for its skyscrapers and modern architecture, the city also boasts a rich history of speakeasies from the Prohibition era.

On this private evening pub crawl, guests have the opportunity to discover these hidden gems and learn about the city’s bootlegging past.

Led by a professional historian, the tour takes participants through a series of local establishments, providing a glimpse into the clandestine world of 1920s Chicago.

Led by a professional historian, the tour takes guests through local establishments, providing a glimpse into Chicago’s clandestine 1920s underworld.

From the unmarked doors to the authentic decor, each speakeasy visit offers a unique and immersive experience, transporting guests back in time.

Uncovering the History of Bootlegging and Racketeering

During the Prohibition era, Chicago became a hub for illicit alcohol production and distribution, as bootleggers and racketeers capitalized on the high demand for forbidden drinks.

Mafia leaders like Al Capone built vast criminal empires, bribing public officials and violently eliminating rivals.

Speakeasies, hidden bars that secretly served liquor, sprung up across the city. Patrons risked arrest to enjoy the forbidden pleasures of cocktails, jazz, and revelry.

This private tour delves into this shadowy underworld, as an expert guide shares captivating stories of the era’s bootlegging operations and power struggles.

Guests can imagine themselves transported back in time, experiencing a glimpse of Chicago’s notorious past.

Dress Code and Attire for the 1920s Experience

To enhance the immersive 1920s speakeasy experience, the tour encourages guests to dress in smart casual attire reminiscent of the era.

This can include stylish suits, dresses, or even period-inspired accessories like fedoras, suspenders, or beaded necklaces.

The dress code is intended to help participants fully enjoy the historical ambiance.

While costumes aren’t required, the tour organizers believe that dressing up adds to the overall sense of adventure and discovery.

This attention to detail helps bring the Prohibition-era settings to life, creating a more authentic and memorable experience for all.

Luxury Transportation and Pickup Locations

The private speakeasy pub crawl in Chicago includes luxury private transportation to ensure a comfortable and convenient experience for participants.

Pickup is available from hotels or venues within the Chicagoland area. Guests must specify their desired pickup location at the time of booking.

Pickup is available from hotels or venues within the Chicagoland area. Guests must specify their desired pickup location at the time of booking.

The tour is wheelchair accessible and near public transportation, catering to a range of accessibility needs.

With seamless transportation and a knowledgeable guide leading the way, guests can enjoy the Roaring Twenties atmosphere without worrying about navigating the city on their own.

Knowledgeable Tour Guides and Their Expertise

As the core of the private speakeasy pub crawl, the professional historian tour guides bring a wealth of knowledge and engaging storytelling to the experience.

Conor and Kai, the two most popular guides, captivate guests with their expertise on Chicago’s bootlegging history and the city’s notorious gangsters.

They take participants on a journey through the 1920s, revealing the hidden locations of former speakeasies and sharing tales of racketeering and illicit activities.

With their dynamic presentations, the guides ensure the pub crawl is both informative and memorable, leaving guests with a deeper appreciation for Chicago’s Prohibition-era past.

Complimentary Amenities and Inclusions

Along With the knowledgeable tour guides, the private speakeasy pub crawl in Chicago offers a range of complimentary amenities and inclusions to enhance the overall experience.

Guests receive luxury private transportation with hotel/port pickup and drop-off, ensuring a seamless journey. Bottled water is provided throughout the tour, keeping guests hydrated.

The tour also guarantees skipping long lines, maximizing the time spent at the hidden speakeasies and local establishments. While alcoholic drinks are available for purchase, they aren’t included in the tour price, allowing guests to explore the city’s historic cocktail scene at their own pace.

Positive Reviews and Memorable Experiences

Numerous reviewers have highlighted the knowledgeable tour guides and unique venues that make the private speakeasy pub crawl in Chicago a truly memorable experience.

Many praise the expertise and engaging storytelling of guides Conor and Kai, who bring the city’s bootlegging and racketeering history to life. Guests rave about the hidden speakeasies and local establishments visited, describing the experience as "one-of-a-kind."

However, some note the tour’s high cost at $330 per person, with alcoholic drinks not included.

Booking and Additional Information

When booking the private speakeasy pub crawl in Chicago, guests can expect a streamlined process. Confirmation is provided at the time of booking, and visitors can arrange pickup from their hotel or a nearby venue within the Chicagoland area.

The tour is wheelchair accessible and located near public transportation for convenience. While the cost of the tour is $330 per person, it includes a professional historian guide, private transportation, and bottled water.

Guests should be aware of the minimum drinking age of 21 and plan to dress in smart casual attire. The booking experience is efficient and tailored to each group’s needs.

The Sum Up

Discover the captivating history of Chicago’s Prohibition-era speakeasies on this exclusive private tour. Led by a local historian, you’ll unlock the secrets of bootlegging and racketeering as you sip on authentic cocktails and learn about the vibrant 1920s atmosphere. This unforgettable experience promises an adventure steeped in history, making it a must-do for any visitor to the Windy City.