Haunted Chicago Booze and Boos Ghost Walking Tour

Haunted Chicago Booze and Boos Ghost Walking Tour: A Spooky Night Out in the Windy City

If you’re looking to spice up your Chicago visit with a mix of history, ghost stories, and lively bars, the Haunted Chicago Booze and Boos Ghost Walking Tour offers a one-of-a-kind experience. For just under $36, you’ll spend about two and a half hours wandering through some of the city’s most storied neighborhoods, stopping at three historic pubs for drinks (at your own expense), and soaking in tales that make Chicago’s haunted reputation come alive. Guided by a costume-clad storyteller, this tour brings history and ghostly legends into the present with humor, enthusiasm, and a good dose of spooky ambiance.

We love that the tour is led by guides dressed in period costumes—think flapper dresses or gangster suits—that instantly set the tone and make the stories feel more authentic. The fact that it’s a walking experience means you get to see Chicago from a different perspective, exploring hidden corners, alleys, and landmarks you might not stumble upon on your own. Plus, the tour’s moderate size (usually around 12 people) ensures a friendly, engaging atmosphere, perfect for curious travelers.

One thing to consider is that this experience is primarily an evening activity and involves walking for about a mile. Weather can impact your comfort—so dress appropriately. Also, since drinks are at your own expense, it’s a flexible outing—you can choose to keep it light or indulge a little more.

This tour suits those who enjoy history, stories of spirits and hauntings, and a fun social vibe. It’s especially popular among couples, friends, or solo travelers wanting a lively yet spooky night out with an authentic local twist. If you love a good ghost story, Chicago’s history, and lively pubs, this tour is likely to become a memorable highlight of your trip.

Key Points

• Authentic storytelling with guides in period costume brings the ghost stories to life.
• A mix of history, local legends, and spooky tales in an engaging walking format.
• Stops at three historic bars, each with their own tales of hauntings and colorful pasts.
• Flexible and reasonably priced at about $36 for a memorable 2.5-hour experience.
• Opportunity to enjoy Chicago’s nightlife in a fun, social setting.
• Limited group size enhances interaction and storytelling quality.

Exploring the Haunted Chicago Booze and Boos Tour in Detail

The Start at Glascotts Saloon: A Prohibition-Era Speakeasy

Your adventure kicks off at Glascotts Saloon, located at 2158 N Halsted St. This family-owned spot has been part of Chicago’s fabric for four generations. Originally a meat market, it transformed during Prohibition into James Morley Soft Drinks, a secretive speakeasy. Your guide, dressed in a 1920s gangster or flapper outfit, will share stories about this hidden past while you settle in for a drink at your own expense.

What makes this stop special is the tangible sense of history. You’re standing where bootleggers and moonshiners once operated, and the stories of that era linger in the air. Visitors often mention the fun of starting the night with a drink in a place that’s seen nearly a century of Chicago’s lively nightlife. The guide’s storytelling makes you appreciate the resilience of this historic watering hole.

Exploring Lincoln Park’s Spooky Corners

From Glascotts, the tour drifts into the picturesque neighborhood of Lincoln Park, where you’ll hear about the ghost of John Dillinger, the infamous gangster whose spirit is said to haunt the alley beside a local theater. The story is a favorite among many, with reviews praising the guide’s engaging narration and local knowledge. It’s an evocative way to see a neighborhood that feels alive with stories—both real and spectral.

The Second Bar: Lilly’s

Next, you’ll stop at Lilly’s, a cozy spot where the guide will tell tales of haunted residents and spectral encounters. This bar provides a more intimate setting, allowing stories to deepen and stories to resonate. Many reviews highlight how well the guide’s storytelling captivates the group, keeping everyone intrigued and entertained.

The Connection to Chicago’s Fire Department: Hook and Ladder

The third stop, Hook and Ladder, is notable for its ties to Chicago’s fire history and its secret door connecting to Halligan, its sister bar. The decor honors the city’s firefighting heritage, and the ghostly tale of John Weiss, a former owner, adds a chilling touch. Since this bar has been operating for over 100 years, it’s steeped in history, and many guests enjoy the authentic, atmospheric environment.

The Route Through Chicago’s Spooky Secrets

Along the walk, you’ll pass by significant spots like Oz Park, where the author of the Oz books, L. Frank Baum, once lived. After dark, the park’s characters and statues seem to take on a more mysterious aura—an ideal setting for ghostly encounters. Some reviews mention that after nightfall, the park feels subtly haunted, adding a delightful layer to your adventure.

Hidden Spirits and Local Legends

The tour also makes a quick stop outside King of Cups, Chicago’s first spirit lounge, which offers craft cocktails and nightly Tarot readings. Employees and patrons have reportedly experienced strange happenings, adding a fun twist for those interested in the supernatural.

The final highlight is the Red Lion, a traditional English pub that opened in 1984 after extensive renovations. This spot’s history as a Western saloon and subsequent transformation make it a perfect setting for ghost stories, especially since multiple spirits are said to linger there. As one reviewer notes, the stories about this place are both spooky and fascinating.

What’s Included and What’s Not

Included in your ticket are a local guide, a tour escort/host, and a take-home souvenir—a fun keepsake like a can cooler or cup. Drinks are not included, allowing you to choose your favorites at each bar, which adds flexibility and helps keep the cost reasonable. Gratuities are also not included, so if you enjoy the guide’s storytelling, tipping is appreciated.

Practical Details

• Meeting Point: Glascotts Saloon
• End Point: Lilly’s Bar
• Duration: About 2 hours 30 minutes
• Price: $35.87 per person
• Minimum age: 21
• Group size: Maximum of 12 travelers, fostering a more personal experience
• Weather: Operates in all conditions—dress accordingly
• Booking: Usually booked around 20 days in advance, indicating strong demand

What to Expect and How to Prepare

Expect a relaxed, engaging walk through some Chicago neighborhoods with plenty of stories, some spooky, some humorous. The pace is moderate, with about 25-30 minutes at each stop, giving ample time to enjoy a drink and absorb the lore. It’s a social experience, so bring your curiosity and maybe a light jacket for comfort.

Authenticity and Value

What sets this tour apart is the combination of history, storytelling, and local nightlife. It offers genuine insight into Chicago’s past and its haunted reputation, all wrapped in a fun, approachable package. Many guests praise guide Katie for her enthusiasm and knowledge, describing her as “incredible” and “very entertaining,” which adds to the experience’s authenticity.

At around $36, it’s a cost-effective evening that blends entertainment with cultural insights. Since the tour is walking, it’s also a good way to see parts of Chicago you might miss otherwise—hidden alleys, historic buildings, and lively neighborhoods.

The Verdict on the Experience

This ghost pub crawl is ideal for adventurous travelers who appreciate history and local legends. It’s particularly suited for those who enjoy storytelling, atmospheric bars, and a lively group setting. The reviews consistently highlight how much fun people had, especially praising the guides’ storytelling skills and the unique venues visited.

If you’re not expecting a haunted house or spooky thrills in a traditional sense, but rather a lively, story-filled evening, this tour delivers in spades.

Final Thoughts

For anyone curious about Chicago’s spooky side, this tour offers a well-paced, engaging way to explore the city’s hidden corners and colorful past. You’ll learn about legendary figures, haunted pubs, and ghostly legends—all while enjoying a relaxed night out. The mix of historical tidbits, storytelling, and bar hopping crafts an experience that’s both entertaining and insightful.

It’s a tour that works best for small groups, those with a sense of humor, and anyone eager to combine history with a bit of ghostly fun. If you value knowledgeable guides, authentic neighborhood insights, and a lively atmosphere, you’ll find this ghost walk to be a highlight of your Chicago trip.

Frequently Asked Questions

Is the tour suitable for non-drinkers?
While drinks are at your own expense, the focus is on storytelling and exploring bars. Non-drinkers can certainly enjoy the stories, but they should be comfortable walking and being in lively pub environments.

How long does the tour last?
It lasts approximately two hours and thirty minutes, including stops at three bars and walking through neighborhoods.

What is the group size?
The tour is limited to a maximum of 12 travelers, which promotes a more personal experience.

Are drinks included?
No, drinks are not included. You can purchase them at each stop as you prefer.

What should I wear?
Since the tour operates in all weather conditions, dress appropriately for the weather—layers and comfortable shoes are recommended.

Can I cancel if I change my mind?
Yes, cancellations are free if made at least 24 hours in advance. Less than 24 hours’ notice results in no refund.

Is this tour suitable for older or younger travelers?
The minimum age is 21, so it’s geared toward adults. The stories and environment are suitable for travelers of all ages within that range.

Does the tour operate in bad weather?
Yes, it runs rain or shine, so dress accordingly. If canceled due to severe weather, a full refund or alternative date will be offered.

How far in advance should I book?
Most people book around 20 days in advance, indicating a popular and well-scheduled tour.

In Closing

The Haunted Chicago Booze and Boos Ghost Walking Tour expertly combines history, local lore, and nighttime pub culture into a memorable experience. It’s perfect for those who enjoy a lively, story-driven outing with a spooky twist, without the need for over-the-top scares. Whether you’re a history buff, a ghost story enthusiast, or just someone looking for a fun night out, this tour provides a fascinating glimpse into Chicago’s haunted past, all while enjoying its vibrant nightlife.