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Discover Chicago’s dark past and hidden stories on this 2-hour Lincoln Park tour, exploring gangsters, ghost stories, and legendary landmarks.

Taking a walk through Chicago’s Lincoln Park neighborhood offers more than just scenic parks and bustling streets. This 2-hour guided tour promises a journey into the city’s darker, more mysterious side, touching on crime, legends, and hidden histories. While some may find it a bit uneven or broad in scope, it’s a solid choice for those curious about Chicago’s Prohibition era and its notorious gangsters.
What makes this experience worth considering? First, the knowledgeable guides are frequently praised for their storytelling ability — they bring Chicago’s gritty past to life. Second, the tour covers a surprisingly wide range of sites, from historic theaters to famous crime scenes, making it a compact but diverse experience. On the flip side, some travelers feel the pace could be quicker and the focus more centered on Lincoln Park itself rather than broader Chicago history.
This tour is ideal for visitors who enjoy storytelling, local legends, and quick historical snippets. If your schedule is tight but you want a taste of Chicago’s gangster era and ghostly stories, this could be a good fit. However, if you prefer more in-depth exploration or a more focused neighborhood tour, you might want to consider other options.

Looking for more options in Chicago? Here are some other experiences worth considering.

We start near DePaul University, a campus shrouded in ghost stories and urban legends. Tales of ghostly sightings in dorms and rumors of hidden tunnels used during Prohibition set an eerie tone. While admission is free, this stop is more about setting the scene for the dark history ahead. The stories here bring to life the university’s long-standing myths, giving a flavor of Chicago’s secretive past.
Next, we visit the Biograph Theatre, a site forever linked with the infamous gangster John Dillinger. It’s where Dillinger was ambushed and shot by FBI agents in 1934, a moment that marked the end of an era of gangland violence. The alley outside is reputed to still have lingering ghostly whispers, adding a touch of supernatural intrigue. Expect a 20-minute stop with plenty of historical context about Dillinger’s reign and his dramatic Hollywood-like end.
Known today as a lively blues club, Kingston Mines holds secrets from its past. Rumors of secret gambling and mob ties during its early days add a layer of danger to its lively reputation. We’ll spend about 20 minutes soaking in its atmosphere, imagining the drama and clandestine dealings that once took place here. The stories make it more than just a music venue—they give it a sense of Chicago’s underground history.
While now a family-friendly park, Oz Park carries the weight of history connected to the 1893 Columbian Exposition. It’s also linked to the notorious serial killer H.H. Holmes, who famously operated his Murder Castle nearby. The contrast between the park’s cheerful appearance and its dark past invites reflection on how even the most picturesque sites can hide grim stories.
One of the most infamous moments in Chicago gang history happened in a garage on Clark Street. On February 14, 1929, seven members of Bugs Moran’s gang were brutally executed, an act widely associated with Al Capone. We spend about 10 minutes recounting this brutal episode, which symbolized the violent clashes of Chicago’s Prohibition-era crime wars. It’s a stark reminder of the city’s turbulent past.
The Cider House at this address offers a glimpse into the speakeasy culture of Prohibition. Surviving the Great Chicago Fire of 1871, this location hints at the clandestine bars and secret operations that kept Chicago’s bootlegging scene alive. The stories of daring escapes and secret deals make this stop particularly lively, even if it’s just from the stories told here.
The final stop takes us to the Lincoln Park Zoo, but it’s not just about animals and scenic views. Beneath the zoo lies a former cemetery, giving rise to ghost stories and eerie encounters reported by visitors. It’s a fitting end to a tour exploring both the lively and the spectral sides of Chicago.

This tour offers a fast-paced journey through some of Chicago’s most infamous crime sites, historical landmarks, and ghostly stories. With a maximum group size of 15, it’s intimate enough for questions but might feel a little rushed if you’re hoping for deep dives into each site. The live commentary from knowledgeable guides is often highlighted as a major plus—they’re good storytellers who can make history feel vivid and real.
The tour price of $29 offers reasonable value for a two-hour experience that covers a broad swath of Chicago lore. However, some travelers noted that the tour could feel a bit slow or superficial, especially if you’re expecting extensive detail about each site. One reviewer mentioned that “we moved pretty slow and didn’t cover a lot of ground,” which suggests it’s more about storytelling than exhaustive history.
Starting at North Lincoln Avenue & North Halsted Street, the tour begins promptly at 2:00 pm. It’s accessible by public transportation, which is convenient if you’re staying nearby. The tour concludes at Stockton & Webster, close to other Lincoln Park attractions like the Conservatory and the zoo. This makes it easy to extend your visit or explore the park after the tour.
With a maximum of 15 travelers, the group remains intimate, fostering interaction and questions. However, some reviews note the pace can be slow, and the coverage might not satisfy those looking for a deep dive into each location. It’s best suited for those with a general curiosity about Chicago’s gangster era and ghost stories, rather than history buffs seeking exhaustive detail.

When thinking about whether this tour provides good value, consider the price of $29. It’s affordable for a two-hour guided experience, especially given the engaging stories and historic sites covered. If you’re interested in Chicago’s crime legends, Prohibition-era history, and ghost stories, you’re likely to find it entertaining and informative.
On the other hand, if your main goal is to explore Lincoln Park itself or get a comprehensive historical overview, you might find this tour a bit scattered or superficial. The value lies in the storytelling and the chance to hear local legends firsthand from experienced guides. It’s an excellent choice for travelers seeking a quick, thematic tour with an emphasis on Chicago’s darker side.

This experience is best suited for visitors who enjoy storytelling and local legends. It’s perfect if you want a quick, engaging overview of Chicago’s Prohibition gang wars, ghost tales, and historic landmarks. It’s also a good option for those wanting a more intimate group experience with a knowledgeable guide who can answer questions and share anecdotes.
If you’re on a tight schedule or a budget, this tour offers a lot of bang for the buck. But if you’re craving a more in-depth exploration of Lincoln Park or Chicago’s history, consider other tours that might focus more on architecture or specific neighborhoods.

How long is the tour?
It lasts approximately 2 hours, making it a manageable experience for most travelers.
Where does the tour start?
It begins at North Lincoln Avenue & North Halsted Street in Lincoln Park.
What is the group size?
The tour is limited to a maximum of 15 travelers, ensuring an intimate setting.
Is the tour suitable for children?
Most travelers can participate, but given the dark themes and crime stories, it’s best suited for older children or teenagers.
Does the tour include any entrance fees?
No, all stops are external visits; admission to sites like Lincoln Park Zoo is not included.
What should I wear?
Comfortable walking shoes and weather-appropriate clothing are recommended, as it’s a walking tour.
Can I cancel if I change my mind?
Yes, you can cancel up to 24 hours in advance for a full refund.
Is there a guide that speaks other languages?
The tour features live commentary from a professional guide, but language options are not specified.
How do I prepare for the tour?
Bring curiosity, a camera if you like, and be prepared for some storytelling that mixes history with local legends.
“Tour was fine! We moved pretty slow and didnt cover a lot of ground. I was hoping for more information specific to Lincoln park, but I would say ab…”

If you’re looking for a lighthearted yet informative way to get a glimpse of Chicago’s gangster past and ghost stories, this tour ticks many boxes. The guides’ storytelling skills are often praised, and the sites visited give a tangible sense of the city’s tumultuous past. While it may feel a bit broad or slow at times, the mix of history, legend, and local flavor offers a memorable two hours.
For those who enjoy stories of mobsters, ghosts, and historic landmarks, and want a guided experience that’s both affordable and easy to fit into a busy schedule, this tour is worth considering. It’s a fun way to learn about Chicago’s darker side without committing an entire day, and the final endpoint offers the chance to explore more of Lincoln Park’s attractions.
In summary, this tour offers a spirited peek into Chicago’s criminal and ghostly tales, brought to life by passionate guides. It’s best for curious travelers who appreciate storytelling over exhaustive detail and want to combine history with a bit of local mystique.