Private tour

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

From US$ 950 per group up to 5

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.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Covid-19 precautions
Special health and safety measures are in place. Check your activity voucher once you book for full details.
Duration 3 hours
Check availability to see starting times.
Skip the line through express security check
Live tour guide
English, Chinese
Pickup included
Your chauffeur and guide will pick you and your group up anywhere within the Chicago city limits
Private group


  • 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
Full 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.
  • 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
Not suitable for
  • People with mobility impairments
  • People under 21 years

Select participants and date



Important information

What to bring

  • Passport or ID card
  • Driver's license

Not allowed

  • Sleeveless shirts

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).
Customer reviews

Overall rating

5 /5

based on 3 reviews

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Star rating:

Kai was an excellent guide for our activity last night. She had so much knowledge of Chicago history and when we requested more of history/ gangster knowledge vs just the speak easy stops, she made a significant pivot to make our activity specific to our requests. Would highly recommend this tour and Kai!

November 8, 2021

Great tour guide and very fun experience.

March 9, 2022

April 4, 2022

Product ID: 289555