Haunted Chicago Booze and Boos Ghost Walking Tour

If you’re after a blend of history, a bit of spooky fun, and a night out with a twist, the Haunted Chicago Booze and Boos Ghost Walking Tour might just be your perfect evening. This tour offers a unique way to explore Chicago’s darker past while enjoying drinks at some of its most historic and haunted bars. With a highly praised guide, atmospheric locations, and storytelling that keeps you hooked, it’s a memorable experience — especially if you love ghost stories and local lore.

We love that this tour combines engaging storytelling, authentic historic bars, and a lively atmosphere. It’s well-paced, offers a glimpse into Chicago’s haunted past, and makes for a fun night with friends or fellow travelers. The costumed guide in period dress adds a flair of authenticity, making you feel like you’ve stepped back into the roaring twenties or the Prohibition era. The only thing to consider is that drinks are paid for separately, which can add up if you indulge at each stop. Still, for around $36, you get a two-and-a-half-hour tour packed with stories and atmosphere — a solid value for a night of entertainment.

This experience is best suited for those who enjoy history, ghost stories, lively pub atmospheres, and a social vibe. If you’re curious about Chicago’s haunted spots but also want a casual, fun night out, this tour hits the mark perfectly.

Key Points

• Authentic Historic Bars: Visit iconic locations like Glascott’s Saloon, Lilly’s, and Hook and Ladder, each with its own ghostly tales.
• Engaging Guides: Local storytellers in period costumes bring history and hauntings vividly to life.
• Balanced Experience: Mix of walking through the city’s spooky corners and relaxing at bars with drinks (own expense).
• Authentic Atmosphere: The tour’s stops and stories reflect Chicago’s Prohibition era and its ghostly legends.
• Flexible Booking: Mobile tickets and free cancellation up to 24 hours before make planning easy.
• Ideal for Adults: Minimum age of 21, making it perfect for those looking for a lively, spirit-themed night.

In-Depth Look at the Haunted Chicago Booze and Boos Tour

The Itinerary Breakdown

The tour kicks off at Glascott’s Saloon — a family-owned spot with four generations of history. Originally a meat market, it became a speakeasy during Prohibition, operating as James Morley Soft Drinks. Your guide, dressed in period costume, will share tales about its secret past and haunted reputation. The 25-minute stop is a fantastic way to set the mood, especially considering Glascott’s is a genuine piece of Chicago’s underground history.

From there, the tour moves through Lincoln Park, where you’ll learn about the ghost of bandit John Dillinger haunting the alley beside a historic theater. This stop adds a dash of true crime appeal to the ghostly tales. Walking through this leafy neighborhood, you’ll also pass Oz Park, where the literary connection to L. Frank Baum — author of “The Wizard of Oz” — adds an extra layer of charm, with some reviewers speculating about ghostly inhabitants after dark.

Next, the group heads to Lilly’s, a bar where you can enjoy a drink and hear about its haunted residents. This 30-minute stop offers a more personal narrative, with stories of spirits linked to the bar’s long history. Reviewers have described the stories at Lilly’s as “very interesting,” and appreciated hearing about the bar’s past in a relaxed setting.

The third stop is Hook and Ladder, a fire department-themed bar connected to its sister, Halligan. The decor honors Chicago’s fire fighters, and the building itself has been serving patrons for over a century. Here, the ghost of John Weiss, a former owner, is said to still linger. The 25-minute visit blends history, a lively setting, and ghostly tales to create an immersive experience.

Along the walking route, the tour passes Oz Park and King of Cups, Chicago’s first Spirit Lounge, both adding colorful local flavor. King of Cups, known for craft cocktails and tarot readings, even has its own ghost stories, making it a fitting stop for anyone interested in spirits — both literal and figurative.

Finally, the group outside the Red Lion — a pub with a storied past dating back to 1984 — reveals the tales of spirits that supposedly haunt this historic site. Once a gritty Western saloon, it’s now a classic English pub with legends of ghostly activity tied to its walls.

The Experience and Atmosphere

The two-and-a-half-hour duration is just right for exploring several locations without feeling rushed. The group size is limited to 12, which makes the experience intimate and allows for personalized storytelling. The guides, like Mallory and Katie, are praised for their knowledge and engaging delivery. Reviewers often mention how the stories kept everyone interested, whether they were seasoned ghost enthusiasts or first-timers.

The costumes and period details help transport you back in time, making the stories feel more alive. The tour’s route is well-chosen, walking through neighborhoods with a haunting past and passing by landmarks that add depth to the stories. The walk is moderate, so travelers should be comfortable with some light physical activity, but nothing strenuous.

The Bars and Drink Options

While your drinks are not included, the bars themselves are part of the attraction. Each venue boasts its own character and haunted reputation. Glascott’s, with its speakeasy origins, provides an authentic setting; Lilly’s offers a cozy, locally loved spot; Hook and Ladder is lively, themed around Chicago’s firefighting heritage; and Red Lion adds a spooky, transformative history.

Expect to purchase drinks at each location if you want to join in the fun. Prices vary, but the overall experience is more about the stories and atmosphere than the bar tab. The take-home souvenir cup or cooler is a nice touch, giving you a memento to remember the night.

The Value and Practical Tips

At just under $36 per person, the tour offers excellent value. For that price, you get a knowledgeable guide, multiple stops at historic bars, engaging stories, and a fun night out. Reviewers frequently mention how the tour is “well worth” the cost, especially considering the quality of storytelling and the unique locations visited.

Booking is straightforward with mobile tickets, and the flexible cancellation policy means you can plan with confidence. Remember, it operates rain or shine, so dress appropriately for weather — layers are always recommended in Chicago, especially after dark.

Who Will Appreciate This Tour?

This experience suits adults who enjoy history, ghost stories, and lively social atmospheres. It’s perfect for groups of friends, couples, or solo travelers looking for an evening of entertainment with a spooky twist. It’s also a great activity for those interested in Chicago’s Prohibition era or haunted legends, offering both entertainment and a dash of local culture.

The Sum Up

The Haunted Chicago Booze and Boos Ghost Walking Tour offers a well-rounded mix of storytelling, historic bar stops, and ghostly tales. With knowledgeable guides, engaging narratives, and a lively atmosphere, it provides a memorable evening that balances fun with cultural insight. The tour’s setting in historic bars with their own haunted reputations makes it feel authentic and immersive.

Whether you’re a ghost enthusiast, history buff, or simply looking for a different way to explore Chicago after dark, this experience is sure to entertain. It’s a great choice for a relaxed, social night out, especially if you appreciate stories that combine local legends with a spirited ambiance.

This tour delivers great value for money and a genuinely enjoyable experience — just be ready to buy a drink or two along the way.

FAQ

Is the tour suitable for all weather conditions?
Yes, the tour operates in all weather conditions. Dress appropriately, as Chicago nights can be cool, especially in the wind.

How long does the tour last?
The experience is approximately 2 hours and 30 minutes, including walking and stops at the bars.

Are drinks included in the price?
No, drinks are purchased separately at each bar.

What is the minimum age to participate?
Participants must be at least 21 years old.

How many people are in each tour group?
The maximum group size is 12, ensuring a more personal experience.

Can I cancel if I change my mind?
Yes, free cancellation is available up to 24 hours before the tour starts.

What kind of guide leads the tour?
A local guide dressed in period costume, often in the style of a 1920s gangster or flapper.

Do I need to book in advance?
Yes, booking about 20 days in advance is recommended, as spots fill quickly.

Where does the tour start and end?
It begins at Glascott’s Saloon and ends at Lilly’s Bar.

What is included in the souvenir?
A take-home commemorative can cooler or cup is provided.

If you’re looking for a fun, atmospheric way to explore Chicago’s haunted past while enjoying some drinks, this ghost walking tour hits all the right notes. It’s a lively, fun, and slightly spooky night that offers a fresh perspective on the city’s history — with a spirited twist.