Chicago Loop Prohibition Tour: Discover Hidden Speakeasies and History
Step into Chicago's underground drinking scene with the Sip Happens: Chicago Loop Prohibition Tour. This app-guided walking experience takes you through hidden speakeasies and secret bars, revealing the city's lively Prohibition-era nightlife. Learn about notorious figures like Al Capone while exploring some of Chicago’s most intriguing hidden spots.
As you stroll through the Loop, you'll uncover stories of gangsters, bootleggers, and the city’s rich history during Prohibition. The tour offers a perfect blend of fascinating tales and vibrant cocktail culture, making it a memorable night out for history buffs and cocktail lovers alike.
Most stops offer the option to purchase drinks and food—recommendations are provided, but you’re free to skip or indulge as you wish. The tour is private, lasts around 1.5 to 2 hours, and is suitable for adults 21 and over. Accessibility options ensure everyone can enjoy this unique Chicago experience.
Frequently asked questions
How long does the Sip Happens: Chicago Loop Prohibition Tour last?
The tour lasts approximately 1.5 to 2 hours.
Are drinks included in the tour?
No, food and drinks are not included. You can purchase beverages and snacks at most stops, with recommendations provided.
Is the tour suitable for all ages?
The tour is designed for adults aged 21 and over. It’s wheelchair accessible, and transportation options are also accessible.
Can I join the tour at any time?
Yes, you can start the tour from any location. The app will guide you to the first stop, and you can press 'Start to Play' whenever you're ready.
Is this a private tour?
Yes, the Sip Happens: Chicago Loop Prohibition Tour is a private experience for your group.
What if I need to cancel?
You can cancel for a full refund if you do so at least 24 hours before the scheduled start time. Cancellations made less than 24 hours in advance are non-refundable.
Free cancellation
Cancel at least 24 hours before the scheduled start for a full refund.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 1.5 hours – 2 hours
Check availability to see start times.
Guided experience
English
Key facts
What's included
Included
- Access to the Sip Happens: Chicago Loop Prohibition Tour
Not included
- Food and drinks are NOT included and must be purchased at each stop. Beverage recommendations are provided but optional.
Itinerary
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Stop 1
Pass through the Palmer House Lobby on your way to the Potter Bar Speakeasy. Admire the ceiling frescos and art collection as you walk!
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Stop 2
Visit Calder's Flamingo while learning about Capone's trial, in the space where the federal courthouse once stood.
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Stop 3
See the western edge of Millennium Park as you move between stops.
Meeting point & pickup
Meet at the starting point
The Crown Fountain in Millennium Park is a convenient meeting spot, across from the Chicago Athletic Association. You can also start from any location—the app will guide you to the first stop. Simply press 'Start to Play' and follow the directions.
Open in Google MapsCancellation & confirmation
Free cancellation
Cancel at least 24 hours before the scheduled start for a full refund.
- 100% refund if canceled at least 1 day in advance
- No refund if canceled less than 24 hours before
Instant confirmation
Your booking is confirmed immediately after checkout.
From $5.00 per person
- Free cancellation
- Secure checkout with our booking partner
