Weird Chicago Tours invites you into the city's shadows with haunted pub crawls and true crime narratives. Discover Chicago’s Prohibition-era secrets, ghost stories, and historic landmarks with lively guides who bring these stories to life.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; requires some standing and walking during stops.
Wildlife
History
Chicago’s reputation as a Prohibition-era stronghold shaped its architecture and nightlife, with figures like Al Capone influencing culture and crime history.
Conservation
Tours focus on responsible urban tourism by encouraging use of public transportation and minimizing waste during pub and walking stops.
Weird Chicago Tours
Weird Chicago Tours invites you into the city's shadows with haunted pub crawls and true crime narratives. Discover Chicago’s Prohibition-era secrets, ghost stories, and historic landmarks with lively guides who bring these stories to life.
Weird Chicago Tours is a Chicago-based tour operator specializing in dark history, true crime, and Prohibition-era experiences. Featured on The Adventure Collective, Weird Chicago Tours offers themed bus tours and adults-only pub crawls that visit historic crime scenes, speakeasies, and sites linked to notorious figures like Al Capone and H.H. Holmes. The company runs signature experiences including 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.
Tours combine on-bus narration with immersive stops and local cocktails where adult-only events apply. Guides present researched historical facts, documented crime accounts, and archival context to ensure accurate storytelling. Transportation is provided for bus-based routes; speakeasy and pub crawl itineraries visit licensed establishments in established Chicago neighborhoods.
Weird Chicago Tours emphasizes safety and respect for historical sites and neighborhoods while delivering lively, educational entertainment. Booking information, schedules, and age requirements are available on the company’s official booking channels. Group reservations, private events, and themed requests can be arranged through standard booking procedures. Reviews and third-party listings provide social proof and visibility for prospective guests. Whether seeking eerie ghost stories, gangster-era history, or speakeasy culture, Weird Chicago Tours offers focused experiences that highlight Chicago’s complex past with informed guides and curated routes. Guests should check age restrictions, accessibility details, and local COVID policies for each tour before booking to ensure a safe, enjoyable experience and cancellation terms.
Tours Offered
7
Seven themed experiences available
Adults-Focused
Multiple tours
Several experiences restrict to adults
Featured On
The Adventure Collective
Listed by a travel publisher
Tour Lengths
Up to 3 hours
Most routes last around three hours
Reserve limited seats for adults-only pub crawls and curated bus tours — tickets and group booking available through official channels.
Dress for the Weather
You'll spend time outdoors at stops during walking and bus tours, so layer accordingly to stay comfortable.
Use Restrooms Beforeboarding
Plan ahead—the bus tours include only one restroom stop, typically near the pickup point at McDonald's.
Arrive Early for Check-In
Arriving 10-15 minutes before your tour start ensures you get a good seat and time to settle in.
Bring a Portable Charger
Extend your phone's battery life to capture photos and notes throughout the tours without running out of power.
Comfortable walking shoes
Necessary for walking segments during the tours and navigating urban sidewalks.
Layered clothing
Allows quick adjustment to Chicago’s changing weather, especially during outdoor stops.
spring|fall|winter
Small backpack or bag
Handy for carrying water, snacks, and extra layers without hassle.
Portable phone charger
Ensures your phone stays powered for photos, videos, and navigation.