Weird Chicago Tours: Haunted & Historical Pub Crawls in Chicago

Chicago’s streets pulse with stories that go beyond the usual landmarks and lakefront blues. Weird Chicago Tours offers a distinctive way to experience the city’s darker chapters and spirited undercurrents through immersive themed pub crawls and historical bus and walking tours. Centered in downtown Chicago, this collection of adventures threads together crime, hauntings, and Prohibition-era secrets—the perfect fit for visitors eager to engage with the city's raw, authentic character.

The city itself, steeped in 20th-century notoriety, is the stage for tours like the Al Capone Daydrinker's Pub Crawl and the Roaring 20’s Speakeasy Tour. These journeys take riders and walkers alike through iconic neighborhoods where Prohibition-era gangsters, illicit speakeasies, and the legendary Chicago Outfit once thrived. On the Haunted History Bus or Downtown Walking Tours, the chilling echoes of spirits and unsolved mysteries are voiced by guides who blend facts, storytelling, and humor to captivate audiences. Stops like the Congress Hotel or Hyde Park ramp up the suspense with tales tied to historical landmarks and eerie events.

What sets Weird Chicago Tours apart is its balance of education and entertainment. Tour guides such as Eric and Kevin bring energy and local knowledge, often involving visitors with reenactments or heartwarming stories that humanize this city’s notorious past. Whether it’s the mysterious Devil in the White City narrative or the pulsating vibe inside a historic brewery, these trips transform Chicago’s streets into open-air theaters of crime, history, and folklore.

Perfect for both longtime locals and first-time visitors, these tours respond to curiosity about Chicago’s grittier side while delivering a social, engaging atmosphere. Practical details like weather readiness and knowing the locations of restrooms are emphasized, ensuring every rider stays comfortable. If you’re drawn to true crime, ghost stories, or the underbelly of America’s gangster era, Weird Chicago Tours offers a distinct gateway into a side of Chicago few get to see. It’s more than a night out—it’s a dive into the city’s compelling shadows and secrets.