Explore Chicago's Dark History — Ghosts, Gangsters & Speakeasies

Weird Chicago Tours: Chicago ghost tours, true crime, and Prohibition experiences

Weird Chicago Tours runs themed bus tours and adults-only pub crawls across Chicago, Illinois. The operator focuses on dark history, gangster-era stories, H.H. Holmes lore, speakeasy culture, and immersive haunted tours. Signature trips include the Al Capone Daydrinker's Pub Crawl, Haunted History Bus Tour, Roaring 20’s Speakeasy Tour, Devil & The White City Tour, Red Light District Pub Crawl, Blood, Guns & Valentines Tour, and the True Crime and Mystery Tour.

What to expect

Guests can expect on-bus narration, researched storytelling, stops at historic sites, and curated visits to licensed bars on applicable pub crawls. Many experiences are adults-only where noted; the Devil & The White City Tour focuses on H.H. Holmes and the 1893 World’s Columbian Exposition. The Haunted History Bus Tour emphasizes firsthand accounts and local legends, while the Al Capone Daydrinker's Pub Crawl highlights Prohibition-era history and notable gangster locations.

Tours at a glance

• Al Capone Daydrinker's Pub Crawl — Experience Chicago's Prohibition history on an adults-only pub crawl that visits iconic bars, Al Capone's secret hideout, and Frank Sinatra's favorite spot while enjoying authentic cocktails.
• Haunted History Bus Tour — An immersive ghost tour that travels beyond drive-by narration to explore Chicago's haunted history, eerie tales, and gangster-era mysteries up close.
• Roaring 20’s Speakeasy Tour — Step back into the Roaring 20s on an adults-only speakeasy tour, visiting hidden gangster sites, speakeasies, and crime scenes with on- and off-bus exploration.
• Devil & The White City Tour — A three-hour historical tour focusing on H.H. Holmes, the infamous 'Murder Castle,' and the 1893 World's Columbian Exposition with documented context.
• Red Light District Pub Crawl — Adults-only exploration of Chicago's notorious districts, madams, and scandals blending narrated bus segments with stops at historic nightlife locations.
• Blood, Guns & Valentines Tour — A 3-hour gangster tour examining Prohibition-era crime scenes and public enemies with immersive stops and documented historical commentary.
• True Crime and Mystery Tour — A daring three-hour tour that uncovers death sites, crime scenes, and Chicago’s most notorious criminal cases for guests seeking in-depth true crime history.

Why choose Weird Chicago Tours

Weird Chicago Tours uses researched narratives and local guides familiar with Chicago neighborhoods and historic records. Tours combine education and entertainment with on-bus storytelling, archival details, and accessible stops. Adult-only pub crawls partner with licensed bars; bus routes include transportation and multiple narrated stops. Guides cite documented sources and historical records where appropriate, and tours are designed to respect neighborhoods and safety.

Booking and practical info

Reservations are available through official booking channels and third-party platforms. Guests should review age restrictions, start times, meeting locations, and cancellation policies before purchasing tickets. Private groups and custom tours can be requested via standard booking procedures. Accessibility varies by route; check specifics for each tour.

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Book a tour to explore Chicago's haunted history, Prohibition-era secrets, and true crime landmarks with experienced local guides. Tickets are limited for adults-only events; advance booking is recommended. For group rates or private experiences contact official booking channels.

Weird Chicago Tours appears in listings like The Adventure Collective and maintains visibility through third-party reviews and publisher features. Prospective guests should read review excerpts and venue notes before attending. The operator emphasizes respectful storytelling and avoids sensationalizing victims while presenting documented historical context. Visitors planning to attend should follow posted venue policies, respect neighborhoods, and arrive on time to fully experience narrated stops and curated routes. Check accessibility details online.