Haunted Chicago Booze and Boos Ghost Walking Tour

Chicago’s ghost stories come with a side of neighborhood bar life on this walk through Lincoln Park. You start at a former Prohibition-era speakeasy, hear about the ghost said to haunt an alley near a theater, and finish at Lilly’s after roughly two and a half hours on foot.

I like two things about the format: the stories are tied to real streets and bars, so you get a feel for the neighborhood along with its spooky lore, and the small group cap of 12 gives the guide room to keep the evening personal. Guides such as Katie, Lara, Mallory, and Bobby have earned particular praise for their humor and storytelling.

One thing to plan for: drinks are not included in the $35.87 price, and the tour is for adults 21 and older. You will also be walking outdoors in whatever weather the evening brings, so wear comfortable shoes and dress for the forecast.

• Begin at a former speakeasy: Glascott’s Saloon started as a meat market and operated as James Morley Soft Drinks during Prohibition.
• Hear stories at three bars: Glascott’s, Lilly’s, and Hook and Ladder are scheduled stops, with drinks available to buy.
• See more than pubs: The route also passes Oz Park, King of Cups, the Red Lion, and a theater alley linked to a John Dillinger ghost story.
• Keep the group small: The tour is capped at 12 people, with a minimum of two adults required to book.
• Budget for the extras: The ticket is $35.87 per person, but any alcohol you order is additional.

A ghost walk with a neighborhood feel

This is not just a string of spooky tales told in a dark room. You move through Lincoln Park, stopping at bars and landmarks while your guide connects local stories to the places around you. The mix suits anyone who likes a little history with their cocktails, or who wants an evening activity that feels less formal than a museum visit.

The guide wears period dress, setting the mood without turning the walk into a costume show. The tour’s tone appears to depend in part on who leads it. Katie, Lara, Mallory, and Bobby are among the guides praised for keeping groups engaged with humor, clear storytelling, and a friendly manner. Alex and Laura have also led tours.

I would book this for the stories and the guide, with the bars as a welcome bonus. If you mainly want a conventional pub crawl, the stops may feel brief; if you want a serious paranormal investigation, the tour is storytelling and sightseeing, not a ghost-hunting session.

Starting at Glascott’s Saloon

Meet the group at Glascott’s Saloon, at 2158 N Halsted Street. The first stop lasts about 25 minutes, and admission is free. You can buy a drink here, but it is not part of the ticket price.

The building’s past gives the tour a useful opening chapter. It began as a meat market and, during Prohibition, was known as James Morley Soft Drinks, when it operated as a speakeasy. Glascott’s has remained family-owned for four generations, a detail that makes this more than a convenient place to gather. Your guide sets out the bar’s history and the night’s spooky theme here.

One practical wrinkle: a bar can be noisy, and one group found the first stop loud enough to make hearing the guide harder. If you have trouble catching a story, move closer to the guide when possible. That is a sensible tactic at any pub stop, especially when other customers are out for their own evening.

Lincoln Park’s alleys and ghost stories

Between the bars, your guide leads you through Lincoln Park and shares stories tied to the neighborhood. One concerns the ghost of John Dillinger, said to haunt an alley beside a theater. The supplied details do not identify the theater, so expect the guide to provide the context on the walk rather than plan around a named attraction.

The value here is the setting. Hearing a story where it is supposed to have happened gives the walk a stronger sense of place than listening to a list of legends indoors. You also get a look at city corners you might otherwise pass without noticing. The mood is spooky, but the focus is entertainment and local lore, not proof of the supernatural.

The route is outdoors and calls for moderate physical fitness. Comfortable shoes matter: you may walk on grass or dirt as well as pavement. The walk lasts about two and a half hours, so plan for steady time on your feet rather than a short stroll between bars.

Lilly’s and its haunted residents

Lilly’s, at 2515 N Lincoln Avenue, is both a bar stop and the tour’s endpoint. The visit lasts about 30 minutes, giving you time to hear about the place’s reported haunted residents and, if you wish, buy a drink. The tour ends here, so you can choose to head off afterward or stay on your own.

Ending at a bar is handy. You do not need to backtrack to the starting point, and the final stop gives the evening a natural place to wind down. Keep in mind that the group’s time there is part of a guided tour, not an open-ended pub visit. If a bar catches your interest, you can return later; several people have found a new favorite spot along the route.

Hook and Ladder’s firehouse character

Hook and Ladder is another scheduled bar stop, lasting about 25 minutes. Its decor honors Chicago’s Fire Department, and the owner is a volunteer firefighter. The bar also has a sister establishment, Halligan, connected by a secret doorway.

Halligan’s building has housed a bar for more than 100 years. Your guide tells the story of its former owner, John Weiss, whose ghost is said to remain connected to the place. These details give the stop a different flavor from a standard cocktail lounge: the focus is on firehouse identity, the connected bars, and a local ghost tale.

As at the other pubs, drinks are available for purchase but not included. If you are going with friends, decide beforehand whether you want to order at every stop or just one. Three bar visits can add up, and you do not need to drink to take part in the stories.

Oz Park, King of Cups, and the Red Lion

The route also passes Oz Park, named for L. Frank Baum, author of the Oz books. The park has Dorothy’s Playlot, Emerald Gardens, and character statues. It is open until 11 p.m., and the tour’s guide may share tales about its supposed ghostly inhabitants after dark.

You pass King of Cups as well, described as Chicago’s first Spirit Lounge. It serves craft cocktails and offers nightly Tarot Card readings, and staff have reported strange happenings that they associate with paranormal visitors. The tour passes the bar rather than listing it as one of the three scheduled drink stops, so do not count on an included visit or time inside.

The Red Lion is another pass-by, where the guide shares stories outside one of Chicago’s best-known haunted bars. It opened in 1984 after a major reconstruction of the former Dirty Dan’s Western Saloon, turning the site into an English pub. The location is said to have several spirits connected to its past. These exterior stops add variety, though they are not the same as sitting down inside each venue.

What $35.87 buys you

At $35.87 per person, the ticket covers the local guide and tour host for about two and a half hours. It also gives you a planned route through several bars and neighborhood landmarks, with the stories and company doing most of the work. Admission at the listed stops is free, but drinks are on your own tab.

I think the price makes the most sense if you value having a guide pull together the local stories and lead the route. You are not paying for a drink package or entry to a collection of attractions. Instead, you are paying for an organized evening with a small group, a costumed guide, and a mix of storytelling and bar stops.

The format can also be a good way to meet people. The group limit is 12, and the tour has worked for couples, friends, families with adult children, and solo participants. If you are traveling alone, you are not required to bring a companion, though at least two adults must book for the tour to run.

Weather, timing, and who should book

The tour operates in all weather conditions, so bring suitable clothing and shoes. The activity also says it requires good weather; if poor weather cancels it, you are offered a different date or a full refund. A minimum number of participants is required as well, and if that minimum is not met, you are offered another date or experience, or a refund.

The experience is offered in English, and you receive booking confirmation at the time of purchase. It is for ages 21 and older, and the booking minimum is two adults. It is typically booked about 20 days ahead, so consider reserving earlier if your Chicago dates are fixed.

Free cancellation is available up to 24 hours before the start time. Cancel later than that, or make a change within 24 hours, and the amount paid is not refunded. Cut-off times follow local time.

This tour suits you if you enjoy ghost stories, neighborhood history, and a relaxed evening with optional drinks. It is less suitable if you want a seated experience, dislike walking in bad weather, or expect alcohol to be included in the ticket.

Should you book the Booze and Boos tour?

I would book it for a sociable night that combines local stories with a few distinct Lincoln Park bars. The strongest part is the guide-led storytelling: enthusiastic guides have helped make the experience funny, welcoming, and informative, while the small group size keeps it from feeling like a large coach excursion.

Go in expecting a walk, three bar stops, and several pass-by landmarks, not a night of included cocktails or a deep paranormal investigation. Bring comfortable shoes, keep room in your budget for drinks, and choose this if spooky tales and neighborhood character sound like a good pairing.

FAQ

How long is the tour?

The tour lasts about two hours and 30 minutes.

Where does the tour start and end?

It starts at Glascott’s Saloon, 2158 N Halsted Street, and ends at Lilly’s Bar, 2515 N Lincoln Avenue, in Chicago.

Are drinks included in the ticket price?

No. Alcoholic drinks are available to purchase, but they are not included in the $35.87 ticket price.

What is the minimum age?

You must be at least 21 years old to take part.

How many people can join the tour?

The maximum group size is 12 people. A minimum of two adults is required to book.

What should I wear?

The tour runs in all weather conditions, so dress appropriately and wear comfortable shoes. The route may include grass or dirt.

Is the tour offered in English?

Yes. The tour is offered in English.

How far ahead is the tour usually booked?

It is booked about 20 days in advance on average. That is a useful guide if you have fixed dates, though it does not guarantee availability.

Can I cancel for a refund?

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