Haunted Chicago Booze and Boos Ghost Walking Tour

Chicago’s Booze and Boos tour mixes three things that fit this city well: old neighborhood bars, unsettling tales, and a long walk through Lincoln Park after dark. You begin at a former meat market and Prohibition-era speakeasy, pass Oz Park and several haunted sites, then stop for drinks and stories inside working Chicago bars.

I like the way the tour ties ghost stories to real buildings, rather than sending you from one unrelated spooky tale to another. I also like the small group size, capped at 12, and the costumed local guide who keeps the evening personal. The main drawback is that this is still a bar crawl, so the first stop can be noisy, drinks cost extra, and the experience depends heavily on the guide leading your group.

Key points before you book

• Three bar stops with drinks sold separately: Glascott’s, Lilly’s, and Hook and Ladder are working bars, not staged haunted attractions.
• Lincoln Park after dark: You walk through neighborhood streets, past Oz Park, theaters, alleys, and old buildings tied to local legends.
• Guide-led storytelling: Katie, Lara, Laura, Mallory, Bobby, Alex, and Brandon have all led tours, with the best guides adding humor, detail, and plenty of personality.
• Small group format: A maximum of 12 people makes it easier to hear the guide and ask questions.
• Plan for real walking: The tour lasts about 2 hours and 30 minutes, and comfortable shoes matter, especially where the route crosses grass or dirt.
• For adults 21 and older: Alcohol is available to purchase, but it is not included in the $35.87 ticket.

Why this Lincoln Park ghost walk works

The strongest part of this experience is its setting. You are not simply standing in a dark room while someone tells a ghost story. You are moving through Lincoln Park, hearing about people and events connected to the streets and buildings around you.

That gives the tales a useful sense of place. An alley beside a theater becomes part of the story about John Dillinger. An old pub is linked to a former owner named John Weiss. A gothic cocktail bar has its own strange reports. The stories may be spooky, funny, or hard to prove, but they are attached to actual Chicago locations.

I also like the balance between walking and sitting down. A full 2.5-hour walk can feel long, especially at night, but the bar stops break up the route. You can order a drink, listen to the guide, and give your feet a rest before heading back outside.

The evening is best understood as a social history walk with ghost stories, not a serious paranormal investigation. You will hear local legends and tales of unusual happenings, but the appeal is the storytelling, the old bars, and the chance to see Lincoln Park from a different angle.

Starting at Glascott’s Saloon

The tour begins at Glascott’s Saloon, at 2158 North Halsted Street. This is a fitting first stop because the building has already lived several lives.

Glascott’s has been family owned for four generations. Before it became a neighborhood saloon, the building was a meat market. During Prohibition, it operated as James Morley Soft Drinks, a harmless name for a speakeasy-era business.

Your costumed guide meets the group here, explains the evening, and begins the first story session. You can buy a drink at the bar, though admission and alcohol are separate. Allow about 25 minutes at this stop.

One practical point: the first bar may be loud. That matters because the guide’s opening stories set the tone for the whole night. If your group arrives during a busy stretch, stay close to the guide and position yourself where you can hear clearly.

The bar is not just a place to grab a drink before the walk. Its Prohibition background gives you a quick introduction to Chicago’s habit of hiding one business inside another. The old meat-market and speakeasy connections make the first stop feel rooted in the neighborhood.

Walking through spooky Lincoln Park

After Glascott’s, the tour heads through Lincoln Park. You will hear stories about the area’s darker side and visit or pass locations connected to hauntings and famous Chicago figures.

The route includes an alley beside a theater associated with the ghost of John Dillinger. That detail gives the walk a sharper edge than a standard pub crawl. You are hearing the story near the place tied to it, rather than receiving a general account of Dillinger somewhere across town.

This section is also where the walking element matters most. You need a moderate level of fitness, and comfortable shoes are a smart choice. One useful tip is to expect some grass and dirt along the route, not only paved sidewalks.

The tour operates in all weather conditions, so check the forecast and dress for the night. The company notes that poor weather can lead to a cancellation, with a different date or a full refund offered in that case. Still, you should arrive prepared for wind, cold, or rain if the tour is running.

Lilly’s and the rhythm of the evening

Lilly’s, at 2515 North Lincoln Avenue, is the listed end point and another bar stop. The group spends about 30 minutes here, hearing about its haunted residents while drinks are available for purchase.

This is a good example of what makes the tour different from a standard walking history program. You are not only looking at facades. You get to sit inside neighborhood bars and hear how their pasts and reported hauntings have become part of their identity.

The pacing also improves here. A guide can tell a story more effectively when everyone is gathered in one place, rather than trying to compete with traffic and sidewalk noise. If you want to ask questions or chat with the guide, the bar stops are your best chance.

The final stop listed for the tour is Lilly’s, but the route also includes Hook and Ladder and several outdoor points. Since the exact order can vary, I would treat the evening as a connected route rather than assume every stop will occur in a fixed sequence.

Hook and Ladder, Halligan, and a secret doorway

Hook and Ladder is one of the more distinctive bar stops. Its sister bar, Halligan, is connected by a secret doorway, and the owner is a volunteer firefighter. The decor pays tribute to the Chicago Fire Department.

The building that houses Halligan has been a bar for more than 100 years. That gives the guide plenty to work with, especially when explaining the former owner John Weiss and the stories attached to the building.

This stop lasts about 25 minutes. You can buy a drink and hear the story inside the bar, which makes the setting part of the experience. The firehouse theme also adds variety. Not every stop is simply an old pub with a ghost attached to it.

For me, this is the sort of detail that helps justify the ticket price. You are seeing places you might otherwise pass without understanding what makes them unusual. The secret connection between the two bars is a small detail, but it gives the stop a character all its own.

Oz Park after nightfall

The route passes Oz Park, a compact park named for L. Frank Baum, author of the Oz books. Baum lived about four miles away, and the park includes Dorothy’s Playlot, the Emerald Gardens, and statues of Oz characters.

The park is open until 11 p.m. The tour does not turn the park into a full attraction visit, but passing it adds a welcome change of mood. The familiar Oz figures contrast with the darker tales being told along the route.

After nightfall, the park takes on a more mysterious quality, and the guide may connect it to ghostly inhabitants. I would not book the tour solely for the park, but it is a pleasant Lincoln Park landmark to see as part of the walk.

This is also a good reminder that the tour is about the neighborhood as much as the bars. You get a mixture of local culture, literature, architecture, and folklore in one evening.

King of Cups and Chicago’s spirit-lounge scene

The route passes King of Cups, described as Chicago’s first Spirit Lounge. It serves craft cocktails and offers nightly Tarot card readings, giving it a different feel from the more traditional taverns.

The bar has its own reported strange happenings. Employees believe otherworldly patrons may have taken a liking to the gothic setting, which makes the location a natural fit for a ghost walk.

You may not stop inside for a full drink here, but the guide uses the exterior and the story to show another side of Chicago’s bar culture. The emphasis is not only on old buildings. It is also on places that deliberately create an atmosphere around spirits of every kind.

If you enjoy themed bars, this will likely be one of the more memorable points on the route. If you prefer a strictly documented history tour, the Tarot and ghostly patron angle may feel more playful than factual.

The Red Lion and layers of bar history

The route also passes outside the Red Lion, one of Chicago’s best-known haunted bars. The building opened as the Red Lion in 1984 after major reconstruction, but it had previously been Dirty Dan’s Western Saloon.

The earlier bar is described as smoke-filled, grimy, and badly run down. It was transformed into a classic English pub, yet the location is still linked to several spirits.

This is a useful stop because it shows how a building can change its appearance without losing its stories. The Red Lion looks and feels different from Dirty Dan’s, but the tales tied to the site remain part of its identity.

You will hear these stories from outside rather than spending the full stop inside. That means the guide’s delivery matters. Strong guides such as Katie, Lara, Laura, and Mallory have been praised for using humor, expressive storytelling, and clear explanations to keep the group engaged outdoors.

The guides make or break the night

The small group size helps, but the guide is the key variable. The most successful guides bring energy, connect with each person, and make the evening feel like an informal night out with someone who knows the neighborhood.

Katie has been singled out for being enthusiastic, funny, and able to keep groups engaged at every stop. Lara has been praised for wit, warmth, and strong stories about Chicago’s past. Laura is another name to watch for, with a style that combines ghost tales with local history.

Mallory has been noted for being descriptive and for making sure nobody falls behind. Bobby Thomas led a group with little previous Chicago experience but still handled the history well. Alex and Brandon have also received positive comments for entertaining storytelling.

The main weakness reported for this sort of experience is also guide-related. One poor outing felt unorganized and too much like a basic bar hop, with little energy or information. That criticism is worth taking seriously. The same route can feel fascinating with a lively storyteller and flat with someone who does not engage the group.

Overall, the guide should be viewed as part of the product, not just the person who leads you from one address to another.

What the $35.87 price really covers

At $35.87 per person, the tour sits at a reasonable price for a 2.5-hour guided evening in Chicago, especially with a group limit of 12. You are paying for the guide, the route planning, the storytelling, and access to several unusual bars and landmarks.

You are not paying for drinks. Alcohol must be purchased separately at each bar, so your final cost depends on how much you order. Keep that in mind when comparing this with a ghost walk that includes refreshments or with a regular self-guided bar crawl.

The value is strongest if you want structure. You could visit bars in Lincoln Park on your own, but you would not automatically hear the stories about Prohibition, John Dillinger, John Weiss, Oz Park, King of Cups, or the Red Lion.

The 97 percent recommendation rate and 4.9 rating from 266 ratings point to a consistently strong experience, but they do not erase the practical concerns. A loud first bar, weather, walking conditions, and an uneven guide can affect your night. I would still call the price fair for the right audience, especially if you like local stories more than polished attractions.

Who should book this ghost tour

I would choose this tour for adults who want an easygoing evening activity with a little history and a little theater. It works especially well for couples, friends, solo visitors, and families with adult children, since the small group format makes it easy to meet people without forcing a formal social event.

It also suits repeat Chicago visitors. The route gives you a reason to spend time in Lincoln Park, and the bars may become useful additions to your own evening plans. Some people have returned to a favorite stop after the tour, which is a good sign that the venues are part of the appeal.

I would skip it if you want a strictly evidence-based account of Chicago’s past, a frightening haunted house, or a tour with all drinks included. I would also reconsider if you dislike walking at night or noisy bars.

Book at least a little ahead if your schedule is tight. The experience is often reserved about 20 days in advance, though last-minute booking can sometimes work. You need at least two adults to book, and the maximum group size is 12.

Free cancellation is available up to 24 hours before the start time. Inside that window, changes and refunds are not accepted unless the company cancels the tour because of weather or because the minimum number of people is not reached.

Final call: book it for stories, not scares

I would book the Haunted Chicago Booze and Boos tour if you want to explore Lincoln Park while hearing stories tied to real bars, alleys, parks, and theaters. The best part is the combination of walking, local character, and costumed storytelling, with a few drink stops to keep the pace comfortable.

Go in expecting folklore, humor, and a social bar crawl with historical details. Do not expect a formal investigation or a ticket that covers your cocktails. Wear comfortable shoes, dress for the weather, stay close enough to hear the guide, and choose this experience when the idea of a good story matters as much as the ghost itself.

FAQ

How long is the Haunted Chicago Booze and Boos tour?

The tour lasts approximately 2 hours and 30 minutes.

Where does the tour begin?

The tour begins at Glascott’s Saloon, 2158 North Halsted Street, Chicago, Illinois 60614.

Where does the tour end?

The listed end point is Lilly’s Bar, 2515 North Lincoln Avenue, Chicago, Illinois 60614.

How much does the tour cost?

The listed price is $35.87 per person.

Are drinks included in the ticket price?

No. Alcoholic drinks are not included, but you can purchase them at the bars during the tour.

What bars are part of the route?

The route includes Glascott’s Saloon, Lilly’s, and Hook and Ladder. It also passes King of Cups and the Red Lion.

Is the tour suitable for anyone under 21?

No. The minimum age is 21.

How many people can join the tour?

The tour has a maximum of 12 participants.

What should I wear?

The tour operates in all weather conditions, so dress appropriately for the forecast. Comfortable shoes are recommended because the route includes walking through areas with grass and dirt.

Can I cancel for a refund?

Yes. You can cancel at least 24 hours before the start time for a full refund. Cancellations or changes made less than 24 hours before the start time are not refunded.