Instant
Confirmation
Mobile
Tickets
No
Booking Fee

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

From
$950.00 /group
Info &
Reviews
Check
Availability

About the activity

Travel back in time to the 1920s, when Chicago was a Prohibition Era hub for lively speakeasies. Your guide, a young, local historian, will lead you through secret entrances to speakeasies once frequented by bank robbers and Chicago gangsters.

  • Free cancellation
    Cancel up to 24 hours in advance for a full refund.
  • Instant confirmation & Mobile tickets
    Receive your ticket right away. Use your phone or print your voucher.
  • Skip the line
    Get priority entry.
  • Private tour
    Avoid crowds with an exclusive experience.
  • Free pickup
    A complimentary hotel pick-up service is offered.
  • Live guiding
    Chinese, English
  • Duration
    3 hours
  • Includes
    • Hotel pickup and drop-off within Chicago city limits
    • 3-hour guided tour with historian
    • Entry to 3-4 working Chicago speakeasies
    • Luxury transportation
    • Chauffeur gratuity
    • Alcoholic beverages (available for purchase)
    • Tour guide gratuity
Highlights & Description

Highlights

  • Enter historic speakeasies via secret passages
  • Hear the colorful stories behind Chicago’s Prohibition Era past
  • Travel around the city in style with a well-versed young guide

Description

Spend an evening visiting the Chicago speakeasies that have been open since the Prohibition Era in the 1920s, many preserved in their original conditions. With your own private group, enter by way of secret entrances and enjoy the same cocktails ordered by infamous Chicago gangsters and bank robbers at these venues nearly a century ago. Relive the glamor of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era.  

Alcohol is available for purchase at the three to four different speakeasy stops. Your private tour guide will make Prohibition Era drink recommendations and tell you the stories behind them. Travel around with your young, professional guide and be chauffeured in luxury transportation, ranging from a luxury SUV to a full-sized luxury motor coach.

Good to know before you go
  • The vehicle used will depend on the size of the group (Mercedes S 550 Sedan, Cadillac Escalade, Mercedes Sprinter, Mini Coach Bus).
Meeting point

Reviews & Ratings

Top 5 Similar Activities in Chicago

See all similar activities

Frequently Asked Questions

1. What is the cancellation policy for this activity?
Cancel up to 24 hours in advance for a full refund.
2. When will I receive the confirmation of my booking?
You will receive an email notification right after your successful payment. If you don't see it in your inbox, check your spam or junk mail folder. When the payment is completed you have the option to download your ticket directly.
3. What does the 'skip the line' ticket mean?
'Skip the line' tickets provide the fastest possible entry with no or very little queuing.
4. What is a private tour?
Private tours offer more advantages and benefits than regular tours. You will have your own private guide for the duration of the tour. You can also customize the itinerary to your specific interests and needs.
5. What is a free pickup?
When a tour company offers free pickup, it means that they will pick you up from your hotel or other designated location at no charge. When making a reservation, you can specify your pickup location.
6. Are mobile tickets enough or do I have to print them?
Tickets don't need to be printed. You can show your ticket from your smartphone as a PDF.
  • Participant
    0-99 years
April 2026
Mon Tue Wed Thu Fri Sat Sun
Check availability