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Duration: 3 hours


Step into the roaring '20s in Chicago with an entertaining Prohibition walking tour. Explore the hidden speakeasies, uncover juicy stories, and discover how Chicagoans enjoyed their secret sips. Join the adventure, mix history with entertainment, and sip a cocktail or two along the way!

🕵️‍♂️ Dive into Chicago's Prohibition-era history and relive the city's secret tales

🥂 Experience the thrill of sipping cocktails in hidden, authentic speakeasies

🎭 Engage with knowledgeable and lively guides who'll make history come to life

🍸 Savor handcrafted cocktails that capture the essence of the Prohibition era


When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Monday, Wednesday, Thursday, and Friday 3:00pm

Practical information

Any restrictions to participate?

  • Age: 21+
  • Physical limitations: Need to be able to walk 1 mile.

Who can you accommodate for?

  • Children: This is not an experience for children.
  • Individuals with disabilities: This tour is wheelchair accessible and service animals are allowed.
  • Pets: Sorry, no pets allowed.

What to expect on the day of the experience?

  • Duration: 3 hours. The tour may go longer based on participant engagement throughout the tour.
  • What’s included: 
    • Fully narrated walking tour
    • Visit 3 speakeasies
    • Food and drinks are not included on the tour, but available for purchase.


  • Who will be present: Your guide and up to 16 total participants.
  • Spectators: No spectators are allowed, everyone must have a reservation.
  • Photo/ video: Photos are encouraged!

How to prepare?

  • Weather dependency: Rain or shine, the tour will be running.
  • Arrival: Plan to arrive 10-15 minutes in advance
  • Parking: Public transportation is encouraged. Like any major city, parking is at a premium. There are lots available nearby, but rates change and you are encouraged to research this if you intend to drive. If you are driving, know your limits and be safe.
  • What to wear: Comfortable shoes and clothing appropriate for weather conditions.
  • What to bring: 
    • A government issued ID for proof that you are at least 21 years of age.
    • Gratuity for your guide, driver and bartenders are customary and appreciated if you enjoy the tour. Suggested gratuity is $10 each for your guide and driver. Tip the bartenders as you normally would outside of a tour setting.


  • Restrooms: Restrooms are available at most tour stops.


Full description

Take a captivating journey back in time to Chicago's Prohibition era, where hidden secrets and speakeasies ruled the city's streets. This immersive walking tour peels back the curtain on the world of "Scofflaws" who defied the law to savor their beloved libations. Follow a guide as they lead you through the city, recounting tales of notorious gangsters and high society elites who frequented these iconic venues, both the "down and dirty" hangouts and the "jackets required" establishments.

Explore the fascinating history of a bygone era when alcohol flowed through the city's veins, and discover how things have changed and yet remained eerily similar. Unearth hidden gems that are right in plain sight as you journey to three unique speakeasies. It's a blend of history, entertainment, and the thrill of uncovering secrets from a time when the city was alive with clandestine activities. This is your chance to step into the Roaring Twenties, savor the mystery, and experience the enduring allure of Prohibition in Chicago!

Returns, exchanges and cancellation

Unused Experience Vouchers can be returned within 30 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 48 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 48 hours in advance means losing the value of your experience.

Duration: 3 hours
Regular price $44
$44 Regular price $47 Sale price
You save $3

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