Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

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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.


  • 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


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

Important Information

  • The vehicle used will depend on the size of the group (Mercedes S 550 Sedan, Cadillac Escalade, Mercedes Sprinter, Mini Coach Bus).

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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