Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Tucked away behind unassuming facades, Chicago’s prohibition-era speakeasies hold a captivating history just waiting to be uncovered. For those seeking an immersive journey into the city’s storied past, the 3-hour private speakeasy cocktail VIP tour offers a unique opportunity to step back in time. Guests can expect an exclusive experience, exploring hidden gems, sipping on classic cocktails, and uncovering the tales of notorious gangsters that once roamed the streets. What secrets lie waiting to be discovered?

This experience made our article of Our Picks For The 3 Best 3 Hour Tours In Chicago.

Key Points

• A 3-hour private speakeasy cocktail tour in Chicago that visits 3-4 working speakeasies with secret passages for up to 5 people at a cost of $950.
• Participants can enjoy classic cocktails similar to those from the Prohibition Era and hear stories of notorious gangsters and bank robbers.
• The tour includes luxury transportation such as a Mercedes S 550 Sedan or Cadillac Escalade, and gratuities for the chauffeur and guide are included.
• Guests must be 21 years of age or older, have a valid ID or passport, and follow a smart casual dress code.
• The tour may not be suitable for individuals with mobility impairments, and cash is recommended for purchasing drinks at the speakeasies.

You can check availability for your dates here:

Tour Overview

This 3-hour private speakeasy cocktail tour in Chicago takes participants on a captivating journey through the city’s Prohibition-era history.

Priced at $950 for up to 5 people, the tour includes pickup within the city limits and the option to book and pay later.

Guests will visit 3-4 working speakeasies, entering through secret passages and hearing stories of infamous gangsters.

Luxury transportation, such as a Mercedes S 550 Sedan or Cadillac Escalade, is provided based on group size.

Participants can purchase cocktails similar to those ordered by figures from the 1920s, and gratuities for the chauffeur and guide are included.

Experience Highlights

The tour takes guests on a captivating journey through Chicago’s Prohibition-era history.

Visitors will:

• Enter hidden speakeasies through secret passages, just as patrons did in the 1920s

• Hear thrilling tales of notorious gangsters and bank robbers who frequented these establishments

• Enjoy classic cocktails similar to those ordered by infamous figures of the era

• Travel in luxury transportation, such as a Mercedes S 550 Sedan or Cadillac Escalade

• Receive drink recommendations from the knowledgeable guide to enhance the authentic speakeasy experience.

Tour Details

On the tour, participants can expect to visit 3-4 working speakeasies during the 3-hour experience.

The transportation provided will be a vehicle type suited to the group size, ranging from a Mercedes S 550 Sedan for smaller groups to a Cadillac Escalade for larger ones.

Participants will be transported in a vehicle tailored to group size, from a Mercedes S 550 to a Cadillac Escalade.

While alcohol is available for purchase at the venues, the guide will provide drink recommendations reflective of the Prohibition Era.

Gratuities for both the chauffeur and tour guide are included in the tour price, ensuring a seamless and enjoyable experience throughout.

Prohibition-Era Speakeasies

Although the roaring 1920s saw the national prohibition of alcohol in the United States, enterprising Chicago entrepreneurs found ways to secretly serve thirsty patrons during this era.

Visitors on the Chicago Speakeasy Cocktail Tour will discover:

• Hidden entrances concealed behind bookshelves, phone booths, or other discreet passageways

• Exclusive clubs where only members and their guests were allowed

• Ornate interiors with lush decor, creating an atmosphere of forbidden luxury

• Stories of infamous gangsters and bootleggers who frequented these clandestine establishments

• Cocktails inspired by the era, recreating the flavors enjoyed by the notorious figures of the Prohibition.

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Gangsters and Bank Robbers

Infamous Chicago gangsters and bank robbers frequented the city’s secret speakeasies during the Prohibition era.

Al Capone, one of the most notorious criminals of the time, was known to visit the speakeasies to enjoy illicit cocktails.

Other infamous figures like John Dillinger and "Baby Face" Nelson also patronized these hidden establishments, seeking refuge from law enforcement.

The speakeasies offered a haven for these outlaws, allowing them to mingle with Chicago’s elite while avoiding detection.

Guests on the speakeasy tour will learn about the fascinating history and colorful characters that made these secret bars such an integral part of the city’s past.

Cocktail Recommendations

While visiting the historic speakeasies, guests can expect to enjoy classic cocktails similar to those ordered by notorious Prohibition-era figures.

Guests can savor classic cocktails enjoyed by notorious Prohibition-era figures at historic speakeasies.

The tour guide will provide personalized drink recommendations, tailoring the experience to each guest’s preferences.

Popular choices may include:

• The Boulevardier – a whiskey-based cocktail favored by gangster Al Capone

• The Sidecar – a brandy-based drink enjoyed by bank robber John Dillinger

• The Bee’s Knees – a gin-based cocktail with honey, a favorite of jazz singer Billie Holiday

• The Negroni – a classic Italian aperitif loved by legendary architect Frank Lloyd Wright

• The Old Fashioned – a timeless whiskey cocktail, popular with notorious gangster Lucky Luciano.

Transportation and Accommodations

For the Chicago Speakeasy Cocktail Tour, the transportation and accommodations are tailored to ensure a seamless and comfortable experience.

Guests are transported in luxury vehicles, such as a Mercedes S 550 Sedan or a Cadillac Escalade, depending on the group size. These high-end vehicles provide a comfortable and stylish ride to the historic speakeasies.

The tour also includes the chauffeur and tour guide gratuity, ensuring a hassle-free experience.

While individuals with mobility impairments may not be suitable for this tour, guests are required to bring a valid ID or passport for identification purposes.

Important Considerations

Although this tour may not be suitable for individuals with mobility impairments, the organizers have ensured that participants must bring a valid ID or passport for identification purposes.

The organizers have ensured that participants must bring a valid ID or passport for identification purposes, though the tour may not be suitable for those with mobility issues.

Plus, the tour is restricted to those 21 years of age and older, as guests will be enjoying alcoholic beverages at the various speakeasy stops.

The dress code is smart casual, with no sleeveless shirts allowed.

Participants are encouraged to bring the following items:

• Passport or valid ID card

• Driver’s license

• Cash for purchasing drinks

• Camera (optional)

• Comfortable walking shoes

Frequently Asked Questions

Are Children Allowed on the Tour?

The tour is not suitable for participants under 21 years old, as it involves visits to speakeasies where alcohol is served. Children are not allowed on this tour.

Can I Bring My Own Alcohol?

No, participants cannot bring their own alcohol on the tour. The tour includes cocktails at the speakeasies, but all alcohol must be purchased directly from the venues. Bringing outside alcohol is not permitted.

How Much Time Is Spent at Each Speakeasy?

The tour typically spends around 45-60 minutes at each of the 3-4 speakeasies visited, allowing guests ample time to explore the historic venues, enjoy cocktails, and learn about the Prohibition-era stories from the knowledgeable guide.

Is There a Dress Code for the Tour?

The tour has a dress code – no sleeveless shirts are allowed. Participants should bring a passport or ID card, and a driver’s license, as these may be required at the speakeasies.

Can I Customize the Tour Itinerary?

The tour itinerary is pre-set and can’t be customized. However, the organizers may be able to accommodate special requests or needs. It’s best to inquire about any customization options when booking the tour.

The Sum Up

This exclusive Chicago speakeasy cocktail tour offers a unique glimpse into the city’s Prohibition-era past. Guests will explore hidden speakeasies, enjoy classic cocktails, and learn captivating stories from knowledgeable guides – all while being transported in luxury. It’s an unforgettable experience for cocktail enthusiasts seeking an immersive adventure through Chicago’s clandestine drinking culture.

You can check availability for your dates here: