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    5. /Chicago Prohibition Walking Speakeasy Tour
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    Chicago Prohibition Walking Speakeasy Tour

    Explore Chicago's Prohibition era through stories of class, nightlife, and rebellion

    4.8 stars• 88 reviews
    From$47/ personincl. taxes and fees

    Duration

    2 hours and 30 minutes

    Highlights

    Step into Chicago's Prohibition era through the contrasting worlds of gangsters and high society. Explore how class divisions shaped the city's drinking culture.

    • Trace Prohibition-era stories beyond the usual gangster tales
    • Compare "down and dirty" nightlife with venues where jackets were required
    • Discover how social class influenced Chicago's drinking culture
    • Explore the contrasting sides of the city's scofflaw lifestyle

    Important details

    • Ages 21+ only
    • Arrive on time, as the tour cannot wait for late arrivals
    • Expect customary gratuities of 15%-20% for guides and restaurant and bar servers

    Cancellation Policy

    All sales are final. With 48 hours' notice, you can reschedule.

    FAQs

    Arrive on time. The tour leaves promptly and cannot wait for late arrivals, and refunds are not available.

    Gratuities for guides and the restaurant and bar servers are customary. Expect 15%–20%.

    Meeting details

    Exchequer, 226 S Wabash Ave, Chicago, IL 60604

    Experience provided by Chicago Prohibition Tours

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #BFQAS4

    Person

    $47.70

    Ages 21+

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    What people are saying

    Review 1 of 5
    5/5

    My wife, her parents and sister, and I joined Jonathan on the Original Chicago Prohibition Tour on a Saturday afternoon in early June. We visited four bars/restaurants, all via bus, learned a lot of history, and had some fun drinks along the way. It was a great tour with balanced pacing at each location, but Jonathan made the tour truly fun. Highly recommended!

    Photo of Jason Karuza

    Jason Karuza

    June 13, 2026

    Review 1 of 1
    5/5

    My wife, her parents and sister, and I joined Jonathan on the Original Chicago Prohibition Tour on a Saturday afternoon in early June. We visited four bars/restaurants, all via bus, learned a lot of history, and had some fun drinks along the way. It was a great tour with balanced pacing at each location, but Jonathan made the tour truly fun. Highly recommended!

    Photo of Jason Karuza

    Jason Karuza

    June 13, 2026

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