Private Speakeasy Pub Crawl In Chicago With Local Historian

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Tour Information

Key Details

  • Mobile Voucher Accepted
  • Hotel pickup Available
  • Duration: 3 Hrs
  • Language:
  • Departure Time :
    4:00 PM
  • Departure Details :
    Traveler pickup is offered
    We can pick you up from your hotel or any other venue within the Chicagoland area. Please specify when booking.
  • Cancellation Policy :
    This activity is non-refundable Tours booked using discount coupon codes will be non refundable.


O|hare international airportur 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 Capones 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 youre really feeling up to it, dress the part, too.

Know More about this tour

Well visit O|hare international airportld bars O|hare international airportf Chicago, many preserved in original condition, that were open during prohibition in the 1920s. Enter by way of the secret entrance and enjoy one of the same cocktails ordered by the infamous Chicago gangsters & bank robbers at these venues nearly a century ago. Al Capones personal favorite was The South-side. Relive the glamour of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era. This tour will visit several of these historic venues still in operation as speakeasies today in and around the Chicagoland area. The tour guide will tell the history behind and make recommendations for prohibition era cocktails, but the price of food and/or drinks is not included in the price of the tour. Dress is fancy casual or For fun, you are welcome to wear period clothing like your Guide.


Professional Historian Tour Guide

Luxury Private Transportation

Bottled water

Hotel/port pickup and drop-off

Guaranteed to skip the long lines

Guaranteed to skip the lines


Alcoholic drinks (available to purchase)

Additional Info

Confirmation will be received at time of booking

Wheelchair accessible

Minimum drinking age is 21 years

Dress code is smart casual

Near public transportation

Most travelers can participate

This is a private tour/activity. Only your group will participate

Face masks required for guides in public areas

Social distancing enforced throughout experience

Regular temperature checks for staff

Contactless payments for gratuities and add-ons

Traveler Reviews

  • 09-May-2022

    We had an amazing time and learned so much. Definitely a night to remember! The Untitled was my favorite place that we went to.

  • 01-Oct-2021

    At $330/person I was surprised that the operator/guide did not provide the drinks at the bars. He was very knowledgeable about the city and we had a great time. It was just too expensive.

  • 15-Sep-2021

    Stefan was an excellent Guide with lots of historic knowledge. The venues were interesting and not something we would have been able to find on our own.

  • 03-Sep-2021

    Our tour guide, Kai, was an amazing wealth of knowledge! I don’t think there was anything about this city that she didn’t know! We rented 1920’s costumes from Chicago Costumes and got a lot of attention which made it even more fun! The pubs we went to had awesome history and were very cool… and the bus was amazing… definitely a high end limo tour! We would definitely recommend this tour!