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Chicago Prohibition Tour

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    What to Expect
    Start your 3.5-hour Chicago Prohibition tour at Harry Caray's Italian Steakhouse — a vintage downtown bar built in 1872 and decorated with antiques and Americana collectibles that give it a sense of old-time Chicago. Be sure to bring along your government-issued ID and some cash to purchase craft cocktails and signature drinks made by expert bartenders on this adults-only tour.

    Your entertaining guide illuminates the underground world of Chicago’s historic speakeasies used during Prohibition and still in operation today. Learn why the sale of alcohol was banned in the US from 1920 to 1933, and discover Prohibition’s key players. Hear anecdotes about lawbreakers like Al Capone and other Chicago mobsters who became powerful during the dry years.

    A coach shuttles you between four establishments, each with a different character. Pull up a stool at a cocktail lounge in Wicker Park where great blues music pumps from an old jukebox. You'll also enjoy a neighborhood bar that claims to be the oldest and longest-running tavern in the Old Town district.

    Wrap up your Chicago speakeasy tour at Exchequer Pub, a Chicago Loop restaurant where historic photographs and posters line the walls of the decades-old bar.
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    Reviews (135)
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    All reviews drinking tour green door spend an evening knowledgeable guide fun tour different parts excellent tour history lesson lots of fun the bus great job cary tavern participants neighborhoods sites stories
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    1 - 5 of 32 reviews
    Reviewed 5 days ago via mobile

    Although well intentioned, the guide rambles endlessly without taking a breath and frankly it was exhausting listening to her. She is knowledgeable , but her delivery was so loud and nonstop it was bordering obnoxious. The bus had no air and no shocks. Cramped, uncomfortable...More

    Date of experience: August 2019
    Thank Debbi5877
    Reviewed 2 weeks ago

    Our tour guide, Elizabeth, was well versed, friendly and knowledgeable. Tour was jam-packed with historical context and side stories focused on numerous movers and shakers during the prohibition period (drys; gangsters; politicians; etc.). The locations visited were interesting and varied -- Club Lucky being an...More

    Date of experience: August 2019
    Thank Mark D
    Reviewed 4 weeks ago via mobile

    This tour greatly exceeded my expectations. The tour guide was very good and provided a great deal of information about how prohibition came about and how it ended in a very entertaining way. The group were soon chatting to each other once we had our...More

    1  Thank dugyoda
    Reviewed 4 weeks ago via mobile

    This tour took us to places in the city we wouldn’t have visited otherwise and we really enjoyed our tour guide, Elizabeth. The gem of the tour is Club Lucky in Bucktown. What a cool, eclectic bar that served fantastic drinks. The bartender was phenomenal...More

    Date of experience: July 2019
    Thank christym14688
    Reviewed 16 July 2019

    Our tour guide, Elizabeth, was very informative and really knows her history! I feel like I took a semester long course on the Prohibition in 3.5 hours. In my opinion, the history lesson was better than the actual locations that you visit. Do not go...More

    Date of experience: July 2019
    Thank kandiss2014
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    Questions & Answers
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    19 August 2019|
    AnswerShow all 2 answers
    Response from christym14688 | Reviewed this property |
    It does not walk by the bean. You only travel bar to bar in a shuttle, no walking.
    3 July 2019|
    AnswerShow all 2 answers
    Response from CathyC741 | Reviewed this property |
    Check with the tour operator. This is a question for them, not for travelers.
    10 June 2019|
    AnswerShow all 3 answers
    Response from amies480 | Reviewed this property |
    If you arrive at the first place early, it is a good place to eat. You will also have time at the last stop. We had appetizers at the middle stops.
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