Chicago’s Lincoln Park: Guns, Guitars & Gangsters

Exploring Chicago’s Lincoln Park through a lens of gangsters, blues, and secret histories is an adventure that promises much more than just a walk. This tour by Tours by Foot offers a glimpse into the city’s notorious past, blending crime lore, musical legends, and even ghost stories all within the peaceful neighborhood setting.

What makes this experience stand out? Firstly, the knowledgeable guides who weave together the city’s darker side with humor and insight. Secondly, the variety of themes, from Prohibition-era speakeasies to legendary blues venues, keeps the tour engaging and dynamic. Lastly, the authenticity of visiting actual historic sites like the site of the Valentine’s Day Massacre and Dillinger’s alley adds a tangible feel to the stories.

A potential drawback? The tour’s focus on Chicago’s criminal past might not appeal to everyone, especially those seeking a purely relaxed sightseeing experience. It’s best suited for curious travelers eager to learn about the city’s gritty history, with a penchant for stories that go beyond the usual tourist spots.

If you’re interested in Chicago’s gangster lore, blues scene, or haunted sites—and enjoy walking through a neighborhood that’s layered with history—this tour offers a compelling mix of facts, stories, and local atmosphere.

Good To Know

• Authentic storytelling from an expert guide makes the history come alive.
• Multiple themes—from Prohibition to blues—provide a well-rounded experience.
• Visit iconic sites like Dillinger’s alley and the Valentine’s Day Massacre location.
• Enjoy vibrant local spots along Lincoln Avenue’s bar district.
• Accessible and flexible with easy meeting points and wheelchair access.
• Great value at $39 for a 2-hour guide-led walk.

You can check if your dates are available here:

A Closer Look at the Tour Experience

The Overview: What’s on Offer

This 2-hour walking tour provides a fascinating peek into Chicago’s Prohibition era, gangland violence, and musical roots—all in the scenic setting of Lincoln Park. Priced at $39 per person, it’s a budget-friendly way to uncover stories that shaped the city’s identity.

Starting at DePaul University, the tour begins in a central location easily reachable from the Fullerton Red Line station. The meeting point is conveniently located at the DePaul University courtyard on Fullerton/Halsted, with a Chipotle across the street for a quick meet-up.

The Itinerary: Sites and Stories

Prohibition & Crime Scenes

As you stroll through the neighborhood, your guide, whose knowledge shines and humor entertains, will narrate tales from the 1920s when Chicago was plagued by bootlegging, speakeasies, and gang wars. You’ll learn about Chicago’s secret gambling operations and mob connections, making it clear how deeply crime was woven into the city’s fabric.

Valentine’s Day Massacre

One of the tour’s most striking stops is the site of the infamous Valentine’s Day Massacre of 1929, where seven members of Bugs Moran’s gang were shot by disguised gunmen. It’s a chilling moment that highlights the violent rivalry between Al Capone and Moran—a story often referenced in Chicago crime lore. The guide will talk about how this event marked a turning point in the city’s gangster conflicts.

Dillinger’s Alley & Biograph Theatre

Next, you’ll visit Biograph Theatre/Dillinger Alley, where the notorious bank robber John Dillinger was ambushed and killed in 1934. This site is particularly atmospheric, and many visitors enjoy imagining Dillinger’s last moments—some even speculate lingering ghostly encounters here, adding an eerie touch.

Historic and Ghostly Sites

The tour also touches on ghost stories linked to DePaul University dormitories, the former cemetery beneath Lincoln Park Zoo, and the shadowy tunnels rumored to be beneath the area. These stories add a layer of intrigue for those interested in paranormal tales.

Music and Nightlife

As you walk along Lincoln Avenue, you may hear the echoes of blues guitars—Kingston Mines, a legendary blues club just a short distance away, played host to many performances during the early days, with rumors of mob-run gambling behind the scenes.

The Human Element: Guides and Atmosphere

According to reviews, the guiding voice is a highlight. One traveler praised their guide as “incredibly knowledgeable and delivering information in an accessible and humorous manner.” Such guides can turn what might seem like a standard history walk into a lively storytelling session, blending facts with local lore.

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The Environment: Neighborhood & Vibe

The tour feels authentic, wandering through residential streets, lively pub districts, and historic sites, rather than just touristy spots. Expect to hear blues music wafting from open doorways and catch glimpses of Chicago’s vibrant nightlife, even if just in passing.

Accessibility and Practicalities

The tour is wheelchair accessible and designed to be flexible. It’s typically scheduled in the afternoon, fitting easily into most Chicago itineraries. There’s no need to worry about payment upfront—you can reserve now and pay later, with free cancellation up to 24 hours in advance.

Valuing the Experience

While $39 might seem modest, the true value lies in the depth of stories and the authenticity of the sites visited. Visiting locations like Dillinger’s Alley or the site of the Valentine’s Day Massacre offers a tangible connection to Chicago’s crime-ridden past. Plus, the lively narration ensures you’re always engaged, making this a worthwhile spend for history buffs or those simply curious about the city’s darker legends.

Who is This Tour Best For?

This walk is perfect for travelers interested in Chicago’s gangster history, Prohibition stories, or blues music. It appeals to those who enjoy walking tours with storytelling rather than just sightseeing, and who want a blend of history, culture, and ghost tales. It’s also suitable for families and individuals with limited mobility thanks to its accessible design.

If you prefer a quieter, more laid-back experience focused solely on scenic views, this might not be your ideal tour. But if you’re looking to understand Chicago’s gritty roots and vibrant underground scene, this tour hits the mark.

Final Thoughts

The Chicago’s Lincoln Park: Guns, Guitars & Gangsters tour manages to combine history, local color, and a touch of ghostly intrigue into a compact, well-paced walk. The knowledgeable guides, authentic sites, and thematic variety make it stand out among Chicago’s many walking options.

It offers real value for money, especially considering the stories you’ll carry home and the atmosphere you’ll soak in. Whether you’re a history enthusiast, music lover, or just want a different perspective on Chicago, this tour provides a memorable glimpse into the city’s complex past.

In summary, this tour is an excellent choice for visitors eager to learn about Chicago’s notorious past while enjoying a relaxed, engaging walk through Lincoln Park. It’s well worth the price, especially for those who appreciate storytelling backed by local knowledge.

FAQ

How long is the tour?
The tour lasts approximately 2 hours, making it a manageable and engaging activity without taking up your entire day.

Where does the tour start?
It begins at the DePaul University courtyard on Fullerton/Halsted, just a few minutes from the Fullerton Red Line station.

Is the tour suitable for wheelchair users?
Yes, the tour is wheelchair accessible, making it inclusive for a range of mobility needs.

What themes are covered?
You’ll explore Chicago’s Prohibition history, gangster violence including the Valentine’s Day Massacre, and local blues venues, along with ghost stories linked to historic sites.

How much does it cost?
The tour costs $39 per person, which offers a good value given the depth of stories and sites covered.

Can I cancel if my plans change?
Yes, you can cancel for free up to 24 hours in advance, allowing flexibility if your plans shift.

What should I bring?
Comfortable walking shoes are recommended, and bringing some curiosity for Chicago’s darker, lively past will enhance your experience.

You can check if your dates are available here: