Haunted Chicago Booze and Boos Ghost Walking Tour

Chicago’s Booze and Boos tour mixes ghost stories with real neighborhood bars, which makes it more social than a standard cemetery or haunted-house walk. You begin at a former speakeasy, follow a route through Lincoln Park, and stop at places with their own strange tales.

I like the small group size, capped at 12, and the way the tour uses ordinary city streets rather than theatrical sets. I also like the costumed guides, including Katie, Lara, Laura, Mallory, Bobby, and Alex, who bring different personalities to the storytelling. The main drawback is that your $35.87 ticket does not include drinks, and one busy bar can make it harder to hear.

Key points to know before you book

• Three Chicago bars anchor the route: Glascott’s Saloon, Lilly’s, and Hook and Ladder provide drinks, atmosphere, and stories tied to their buildings.
• The tour stays in Lincoln Park: You’ll pass Oz Park, the alley linked to John Dillinger lore, King of Cups, and the Red Lion.
• The guide makes the difference: Katie, Lara, Laura, Mallory, Bobby, and Alex have all led engaging versions of the tour.
• Drinks cost extra: Your ticket covers the guide and tour host, but you buy alcoholic drinks at the bars.
• The group is intentionally small: A maximum of 12 people makes it easier to hear stories and ask questions.
• Plan for a real walk: Wear comfortable shoes, since the route can include grass, dirt, and city sidewalks.

Why this Chicago ghost walk works

Many ghost tours rely on grand claims and darkened buildings. This one takes a more casual route. You meet in a neighborhood bar, walk between several stops, and hear stories where the events are said to have happened. The result feels less like a staged attraction and more like an evening out with a local storyteller.

The booze is part of the format, not a bonus hidden in the ticket price. You can order at the bars along the way, but each drink is your responsibility. That makes the tour flexible for your budget, though it also means the final cost depends on how much you order.

At $35.87 per person, the tour is reasonably priced if you want a guided evening that combines three drinking stops with city history and ghost lore. It is less of a bargain if you want a long, serious architecture walk or if you do not plan to drink. The appeal is the combination: a compact neighborhood tour, several atmospheric bars, and a costumed guide who keeps the pace lively.

The 12-person limit matters. A small group helps you stay together on city streets and makes it easier to hear the guide outside a bar. It also creates a more relaxed setting for solo bookers. One solo participant found the group welcoming, which is useful to know if you are in Chicago on your own.

Starting at Glascott’s former speakeasy

The tour begins at Glascott’s Saloon, at 2158 North Halsted Street. You meet your guide and group there, then settle in for the first story and a drink if you wish. Admission to the bar is included in the tour, but alcoholic drinks are not.

Glascott’s has been family owned for four generations. The building began as a meat market and later operated during Prohibition as James Morley Soft Drinks, a name that concealed its speakeasy role. That detail gives the first stop a useful link to Chicago’s past without needing much setup.

This is also where the guide’s costume and delivery begin to shape the evening. The guides are not simply pointing out buildings and reading dates. The strongest versions of this tour use jokes, character, and dramatic timing to make the stories easy to follow.

One practical warning: the first bar can be loud. If you have trouble hearing in busy rooms, stand near the guide and do not wait until the story has started to move closer. The noise is a small issue, but it can affect the opening minutes.

Walking through Lincoln Park’s spooky side

After Glascott’s, you head through Lincoln Park. The walk gives the tour a sense of place that a bar-only crawl would lack. You are not just hearing that Chicago has ghost stories. You are moving through the streets, alleys, parks, and buildings connected to them.

One stop focuses on the ghost of John Dillinger, said to haunt the alley beside a theater. The value here is visual. You see the setting as the guide explains the story, which makes the tale easier to remember than one told in a dark room with no local reference.

The tour also passes Oz Park, a small green space named for L. Frank Baum, author of the Oz books. The park includes Dorothy’s Playlot, the Emerald Gardens, and statues of characters from the stories. It is a welcome change of pace from the bars and alleys.

Oz Park stays open until 11 p.m. According to the tour’s lore, after dark you might encounter some of its ghostly inhabitants. Even if you treat that as storytelling rather than fact, the park adds a pleasant visual break and a bit of Chicago literary history to the route.

Wear shoes you can walk in comfortably. The route is not described as strenuous, but the evening can include grass and dirt as well as pavement. A moderate fitness level is expected, and poor footwear can turn a fun 2.5-hour outing into a tiring one.

Lilly’s and the stories of its residents

Lilly’s, at 2515 North Lincoln Avenue, is both a bar stop and the tour’s listed endpoint. You spend about 30 minutes there, hearing about its haunted residents and ordering a drink if you choose.

This is the longest listed bar stop, so it gives the guide room to build a story rather than rush through a quick supernatural anecdote. It is also a practical place to decide if you want another drink, since the tour ends here.

The endpoint makes planning fairly simple. You do not need to return to Glascott’s after the tour, and the route finishes in the same general Lincoln Park area. Still, keep the exact meeting and ending addresses handy because they are on different streets.

A recurring strength of the tour is the guide’s ability to make the group feel connected. Katie is repeatedly praised for keeping people engaged and including everyone. Lara is known for a witty style, while Mallory has been described as especially attentive about keeping the group together. These differences matter because the guide, not the drink list, determines how much you get from the evening.

Hook and Ladder and the John Weiss story

Hook and Ladder is another major stop, with about 25 minutes set aside for the visit. The bar and its sister venue, Halligan, are connected by a secret doorway. That architectural oddity alone gives the stop a sense of discovery.

The owner is a volunteer firefighter, and the decor honors Chicago’s Fire Department. Halligan’s building has served as a bar for more than 100 years, adding a strong local connection to the stop. You also hear about John Weiss, a former owner whose ghost is said to remain connected to the place.

This is the kind of stop that works best when you enjoy buildings with layers. You get a bar, a piece of neighborhood history, firehouse-inspired decor, and a ghost story tied to a former owner. It is more specific than a generic tale about a haunted room.

Ordering can take time in a group. One useful suggestion is to ask whether the bars can help the tour group order together or provide a quicker way to buy drinks. The tour does not include special drink service, so you should allow for some waiting, especially if the room is busy.

King of Cups and the Red Lion

The walking route also passes King of Cups, described as Chicago’s first Spirit Lounge. The bar focuses on craft cocktails and offers nightly Tarot card readings. The tour points out unusual happenings that have led employees to believe that otherworldly regulars visit the gothic setting.

You may not stop there for a full drink, but it adds variety to the walk. Not every location is a formal bar visit. Some are exterior storytelling points, which keeps the evening moving and lets you see more of Lincoln Park.

The route also passes the Red Lion, one of Chicago’s best-known haunted bars. It opened in 1984 after a major reconstruction of the former Dirty Dan’s Western Saloon. The old place is described as smoky, grimy, and badly run down before it became a classic English pub.

The Red Lion’s ghost stories are tied to the site itself, not just to a decorative theme. That makes the location worth seeing even if you do not go inside. The guide uses the building’s earlier life to explain why several spirits are said to remain connected to it.

These passing stops are important to the overall balance. If the tour only moved from one bar stool to another, it would feel like a regular pub crawl with a spooky label. The parks, alley, theater area, and exterior landmarks give you a better sense of the neighborhood.

The guide matters more than the ghosts

The strongest part of this experience is the human element. Guides such as Katie, Lara, Laura, Mallory, Bobby, and Alex have led this tour, and each brings a different approach. Some lean into jokes and theatrical delivery. Others focus more on Chicago history and the details behind each haunting.

Katie receives especially strong praise for her energy, warmth, and storytelling. Lara is often noted for being funny and personable. Laura brings a mix of ghost stories and Chicago background. Mallory is praised for descriptive storytelling and making sure nobody gets left behind.

Bobby has also led the tour, including for a group that enjoyed the evening enough to eat together afterward. Even though he was new to Chicago, he brought enough historical preparation to keep the stories moving. That detail suggests the tour’s guide training and presentation can matter as much as local familiarity.

There is one clear caution. A less energetic guide can make the tour feel like a simple bar hop, and that is not what every booker wants. If you want a lively performance, the tour depends heavily on who leads your departure. The small group can help, since a good guide has more room to respond to the people in front of them.

Price, drinks, timing, and weather

The ticket costs $35.87 per person and covers a local guide and tour host. Alcohol is extra, so budget for drinks separately. You can keep the total modest by ordering little or nothing, or spend more if the bar stops are a major part of your evening.

The tour lasts about two hours and 30 minutes. That is long enough for several stories and three bar visits without becoming an all-night commitment. It also works well as a first-night activity or a final evening in Chicago, especially if you want to find bars you might revisit later.

The experience is offered in English and uses a mobile ticket. You must be at least 21, and at least two adults are required to book. Children and underage members of a larger group cannot join simply because the walk itself takes place outdoors.

The tour operates in all weather conditions, so bring suitable clothing. The cancellation terms also state that poor weather can lead to a new date or a full refund. If rain or severe conditions are possible, check the status before heading to the meeting point.

You can cancel for a full refund up to 24 hours before the start time. Changes or cancellations within 24 hours are not accepted for a refund. The tour can also be rescheduled or refunded if the minimum number of people is not met.

Who should book this tour?

I would choose this for adults who want a social evening with some history, some folklore, and a few drinks along the way. It suits couples, friends, solo bookers, and anyone who enjoys hearing a story while standing in the place where it is supposed to have happened.

It is also a good choice if you want to see Lincoln Park at night without committing to a long formal history walk. The route adds Oz Park, old bars, a theater-side alley, and several unusual buildings to your Chicago plans.

I would skip it if you want hard proof for every supernatural claim, a quiet sit-down tasting, or a fully planned drink package. The stories are the entertainment, and the alcohol is purchased separately. A busy bar or an unenthusiastic guide can also weaken the experience.

Should you book the Booze and Boos tour?

Book it if you like small-group storytelling, local bars, and a little theatrical fun. At $35.87, the price is fair for 2.5 hours of guiding and several stops, provided you understand that drinks cost extra.

For the best evening, wear comfortable shoes, arrive ready to listen in noisy rooms, and keep your schedule flexible after the final stop at Lilly’s. If Katie, Lara, Laura, Mallory, Bobby, or Alex is leading, expect a guide-led experience where personality plays a big role.

This is not a solemn study of Chicago’s past. It is a lively walk through Lincoln Park that uses haunted lore to show you bars, parks, alleys, and stories you might otherwise miss. For many people, that mix is exactly the point.

FAQ

How long does the Haunted Chicago Booze and Boos tour last?

The tour lasts approximately two hours and 30 minutes.

Where does the tour begin?

The meeting point is Glascott’s Saloon, 2158 North Halsted Street, Chicago, Illinois 60614.

Where does the tour end?

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

Are drinks included in the ticket price?

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

Is there an age requirement?

Yes. All participants must be at least 21 years old.

What happens if I need to cancel?

You can receive a full refund if you cancel at least 24 hours before the experience begins. Cancellations or changes within 24 hours are not refunded.