Explore Chicago’s Underworld: The Al Capone Daydrinker's Pub Crawl
Difficulty
easy
Duration
2–3 hours
Fitness Level
Basic walking stamina is sufficient; no special fitness level required.
Overview
Experience Chicago like never before with the Al Capone Daydrinker's Pub Crawl. Walk the streets once ruled by gangsters, visit historic bars, and savor Prohibition-inspired drinks on this unique guided tour.
Al Capone Daydrinker's Pub Crawl
3 Hours • For Adults Only
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Adventure Photos
About This Adventure
Experience Chicago's Prohibition history like never before on this exclusive adult-only pub crawl. Visit iconic bars, including Al Capone's secret hideout and Frank Sinatra's favorite spot, while enjoying authentic cocktails. Discover the hidden side of the city in a unique, uncrowded setting that brings the past to life.
Weird Chicago's swankiest tour returns and takes adults (21 and older only) on a Prohibition history pub crawl to some of Chicago's coolest -- and most notorious -- bars! Stops may include the only bar openly operated by Al Capone during Prohibition, complete with secret escape tunnels; the first bar to open after the Great Chicago Fire; Frank Sinatra's favorite hangout; and many others! This is your chance to take an uncrowded look at places too busy to see at night, to see a side of "Hidden Chicago" that few ever get to see, and to start your evening right with some authentic Chicago cocktails!
Duration
3 Hours
Meeting Location
600 NORTH CLARK STREET (Outside of McDonalds)
Adventure Tips
Wear Comfortable Shoes
You'll be walking several blocks between bars; sturdy shoes will keep your feet happy.
Bring ID
You must be 21 or older to participate and purchase alcohol on this crawl.
Stay Hydrated
Between drinks and walking, drinking water will keep you energized throughout the tour.
Pace Yourself
Enjoy each stop responsibly to fully soak in the history and ambiance.
Local Insights
Wildlife
- Pigeons frequent most city parks and streets, adding to the urban atmosphere.
- Sparrows and other small birds common around outdoor patios.
History
Chicago’s Prohibition history runs deep, with Al Capone shaping much of its 1920s crime culture.
Conservation
This tour promotes responsible nightlife and respect for historic preservation in Chicago’s downtown area.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Comfortable Walking Shoes
Essential for navigating city streets comfortably during the crawl.
Valid Photo ID
Necessary to purchase alcoholic drinks and verify age.
Light Jacket or Sweater
Chicago can be breezy in fall evenings, a layer keeps you warm.
fall specific
Reusable Water Bottle
Staying hydrated during the walk is important, especially in warmer months.
summer specific