Haunted Chicago Booze and Boos Ghost Walking Tour

The Haunted Chicago Booze and Boos Ghost Walking Tour offers a lively and spooky journey through the city’s haunted history, all for just $35.87 per person. With a duration of approximately 2 hours and 30 minutes, this tour combines storytelling with visits to three historic bars, making it ideal for those interested in Chicago’s darker tales and vibrant bar scene. Led by a costumed guide dressed as a 1920s gangster or Flapper, the experience brings the city’s ghostly past to life in a fun and engaging way. The tour is designed for adults aged 21 and over, and its mobile ticket system ensures smooth check-in. Booking in advance—typically about 20 days ahead—is recommended to secure a spot.

While the tour covers a mile-long route, it’s accessible to most with moderate physical fitness, and operates in all weather conditions, so dressing appropriately is advised. Expect a mix of historical facts, spooky legends, and a lively atmosphere—all set against Chicago’s iconic and secretive corners. This tour excels at creating a memorable night filled with stories, spirits, and historic charm, ideal for fans of ghost stories, history buffs, or anyone looking for a unique evening out.

Key Points

• Affordable and well-rated at 5.0/5 from 166 reviews
• Led by a lively, period-costumed guide dressed as a 1920s gangster or Flapper
• Visits three historic bars, with options to purchase drinks at each stop
• Explores Chicago’s haunted sites, including cemeteries, alleys, and hidden corners
• Includes a take-home souvenir, such as a commemorative cup or can cooler
• Operates in all weather, so dress for the conditions and plan accordingly

Starting Point at Glascotts Saloon in Lincoln Park

The tour begins at Glascotts Saloon, a family-owned venue with a history stretching over four generations. Originally a meat market, it transformed into a Prohibition-era speakeasy known as James Morley Soft Drinks during the 1920s. The guide shares stories about its secret past, making it a fitting first stop. The visit here lasts about 25 minutes, during which guests can enjoy a drink of their own or simply soak in the atmosphere.

Exploring Lincoln Park’s Haunted Corners

Beyond the first bar, the route takes guests through Lincoln Park, where spooky legends come alive. One highlight is the alley beside a historic theater, haunted by the ghost of John Dillinger. As the tour ventures through this area, the guide reveals tales of Chicago’s haunted past and its famous spirits, blending historical facts with ghost stories. The walk offers a chance to experience the city’s darker side under the night sky, with the park itself open until 11 pm.

Visiting Lilly’s: Tales of Haunted Residents

The second stop is Lilly’s, a cozy bar where further ghostly stories unfold. The guide shares details about haunted residents connected to the bar, enriching the experience with local lore. Guests are encouraged to enjoy a drink here while listening to spine-tingling tales. This stop lasts about 30 minutes, providing a relaxed atmosphere to absorb the stories and soak in the historic setting.

The Secrets of Hook and Ladder and Halligan

Next, the tour visits Hook and Ladder, a fire-themed bar with over 100 years of history. Its unique feature is a secret doorway connecting it to Halligan, a sister bar. The owner’s background as a volunteer firefighter adds to the thematic decor honoring Chicago’s fire department. Here, the guide recounts tales of John Weiss, a ghostly former owner, tying the bar’s history to ghostly legends. The visit lasts about 25 minutes, with opportunities to purchase drinks and enjoy the ambiance.

Passing Iconic Landmarks: Oz Park and King of Cups

As the route continues, it passes Oz Park, a charming spot named after L. Frank Baum, the author of the Oz books. Visitors can see Dorothy’s Playlot, Emerald Gardens, and character statues, and imagine the ghostly inhabitants that might linger after dark.

Nearby, the King of Cups Spirit Lounge draws attention with its gothic decor and reputation for hauntings. The bar offers craft cocktails and nightly Tarot Card readings, adding to the mysterious vibe. Employees believe some otherworldly patrons have adopted the bar as their watering hole, making it a fun, spooky stop.

The Historic Red Lion and Its Haunting Stories

One of the most famous haunted bars on the route is the Red Lion, which opened in 1984 in a building with a long history as Dirty Dans Western Saloon. After extensive reconstruction, it became a classic English pub filled with stories of spirits tied to the location. Guests learn about the bar’s ghostly legends and the multiple spirits believed to haunt the premises, adding a supernatural twist to the drinking experience.

Tour Logistics and Group Size

This tour is organized by Nightly Spirits and features a maximum of 12 travelers, ensuring an intimate and engaging experience. The meeting point is Glascotts Saloon, and the end location is Lilly’s Bar. The guide provides a take-home souvenir, such as a can cooler or cup, to remember the night. The tour operates rain or shine, so dressing warmly or appropriately for the weather is recommended.

The Guide and Atmosphere

Guides are known for their knowledgeable storytelling and enthusiasm. Reviews highlight guides like Katie and Mallory, who bring history and legends to life with energy and depth. Guests appreciate the entertaining narratives and the unique bar visits, which make the experience both fun and informational. The costumed guides add an immersive touch, enhancing the spooky atmosphere.

Customer Satisfaction and Ratings

With a rating of 5.0/5 from 166 reviews, this tour consistently receives high praise. Reviewers commend the interesting stories, lively guides, and cool bars. Many mention the value for money and the entertaining storytelling, making it a popular choice for a memorable night out in Chicago. Some note that the guides’ enthusiasm makes a big difference, as well as the quality of the bars visited.

Cancellation and Booking Policies

Guests can cancel free of charge up to 24 hours before the tour, making it flexible for changing plans. The tour is subject to weather conditions, and if canceled due to poor weather, an alternative date or full refund is offered. Due to minimum participant requirements, early booking is advisable to guarantee a spot.

The Sum Up: A Spooky Night in Chicago

The Haunted Chicago Booze and Boos Ghost Walking Tour offers a fun, engaging way to experience the city’s haunted past while enjoying some of its historic bars. Combining storytelling, local legends, and drinks at three different venues, this tour provides a balance of history, entertainment, and a touch of the supernatural—all within a friendly, small-group setting.

Ideal for adults over 21 seeking a unique nocturnal adventure, it stands out for its affordable price, lively guides, and atmospheric stops. While the tour involves walking and some standing, it remains accessible for most with moderate fitness. Whether you’re a history buff, ghost enthusiast, or just looking for a different way to explore Chicago, this tour promises a memorable night filled with stories and spirits.

Frequently Asked Questions

Is this tour suitable for non-drinkers?
Yes, the tour does not include free drinks; guests can purchase beverages at each bar. It’s primarily about the stories and the experience, so non-drinkers can comfortably enjoy the tour without pressure.

How long is the entire tour?
The tour lasts approximately 2 hours and 30 minutes, with stops at three bars and walking between locations.

Is there an age restriction?
Yes, participants must be at least 21 years old to join, due to the alcohol-related stops.

What should I wear?
Since the tour operates in all weather conditions, dressing in comfortable, weather-appropriate clothing is recommended, especially for outdoor walking segments.

Can the tour be canceled?
Yes, cancellations are free if made more than 24 hours in advance. If canceled within 24 hours, the full amount paid will not be refunded.