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Private Speakeasy Pub Crawl in Chicago with Local Historian

icon 3 hours Mobile ticket Free Cancellation
Tickets from € 859.80

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Our Prohibition Era Speakeasy Pub Crawl is filled with cocktails and a perfect venue for bachelor or bachelorette parties, corporate events, or just a fun night out on the town to celebrate life and your friends. Hosted by a local historian, the tour makes stops at: • Al Capone’s neighborhood • Old Chicago bars • Prohibition era establishments  We transport you back in time to the 1920s, entering our venues through secret openings that really shed light on what the city was like 100-years ago. Relive the glamour of this time period while listening to stories of the rampant racketeering and bootlegging. If you’re really feeling up to it, dress the part, too.
  • Bottled water
  • Professional Historian Tour Guide
  • Guaranteed to skip the long lines
  • Luxury Private Transportation
  • Hotel/port pickup and drop-off
  • Alcoholic drinks (available to purchase)
Departure Point

Traveler pickup is offered

We can pick you up from your hotel or any other venue within the Chicagoland area. Please specify when booking.

  • Wheelchair accessible
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Minimum drinking age is 21 years
  • Dress code is smart casual
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
mirandagX7083FL
12 Aug 2024
The tour guide was so knowledgeable and friendly!! All the bars we visited were excellent. I wanted to do a pub crawl while in Chicago, and I am so glad I chose this one. Highly recommend!
jordanaN1711YW
03 Aug 2024
Perfect way to celebrate my birthday! Went to new pubs that are definitely gonna be my new favorite places to frequent. And the tour guide gave us so much fascinating historical context.
Anna_C
20 Feb 2023
I booked this speakeasy tour for a joint bachelor / bachelorette party I was hosting and it was wonderful! Our tour guide, Conor, picked great places to accommodate our group of 16. He and our driver, Melvin, showed up 15 minutes early and kept us on track all day, they even made sure we could get a group photo with a good view of the city. Conor made the whole experience very easy and memorable.
This tour in Chicago is organized by Chicago Tours

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We always double-check the availability with our local partners for each booking. Even though this is usually a swift process, it can take up to 24 hours. Once this process is completed you will receive your voucher or ticket by email. If our local partner is not able to confirm your booking we will offer you the best possible alternative. If the new date and/or time doesn’t fit your itinerary, we will reimburse the full amount paid.
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