Haunted Chicago Booze and Boos Ghost Walking Tour

Chicago’s ghosts love a good drink. This walking pub tour pairs period-dressed guides with real stories from Lincoln Park and beyond, mixing Prohibition-era lore with spirits tied to specific bars. I like that it feels social without turning into a chaotic party.

Two big reasons I think you’ll enjoy it: first, the pace is built for a fun night out—around 2 hours 30 minutes with short stops and plenty of walking time to connect the dots. Second, the stops aren’t generic. You start at Glascott’s Saloon (meat market turned speakeasy), then hit bars that come with their own spooky, specific background.

One possible drawback: since it’s a bar crawl format, the experience depends on how your group and guide keep energy up. If you’re aiming for pure history-only, you may want to manage expectations, because you will be spending time inside lively pub spaces and ordering at your own pace.

Key things that make this tour worth your evening

• Small group size (up to 12), so the guide can actually talk to everyone
• Costumed, local guide storytelling that ties Chicago locations to hauntings
• Three themed pub stops where each location has a different supernatural angle
• Lincoln Park route moments like an alley tied to John Dillinger lore
• Oz Park at night (open until 11pm), with Dorothy-style statuary and possible ghost vibes
• Tarot and cocktails at King of Cups, plus classic haunted pub stories at the Red Lion

A 2.5-hour Booze and Boos walk through Lincoln Park

This is a 2 hours 30 minutes night tour built around a simple idea: you see the city on foot while a guide tells you why certain spots feel off-limits after dark. The whole thing runs from Glascott’s Saloon to Lilly’s Bar, so you don’t end up scrambling for transit at the end.

The tour is adult-only, since the minimum age is 21, and alcohol is not included in the ticket price. So think of your money as paying for the walking, the guide, and the venue access/time—not for a free pour.

Also note the physical side: it’s listed as moderate fitness, and one review mentioned walking in grass and dirt. That means comfortable shoes are not optional, even if you’re just out for one night.

Start at Glascott’s Saloon: speakeasy beginnings and a costumed welcome

You meet at Glascott’s Saloon, 2158 N Halsted St. This is a smart first stop because the setting already has layers. Glascott’s has been family-owned for four generations, and the building’s past isn’t just trivia—it sets up the entire tone of the night.

Before the Prohibition connection, the building was originally a meat market. Then, during Prohibition, it became known as James Morley Soft Drinks and operated as a speakeasy. Your guide—often in period dress—uses that shift to explain how Chicago’s nightlife culture developed, and why those changes can create long-running ghost stories.

You’ll spend about 25 minutes here. There’s usually a meet-and-greet feel first, then the stories start immediately. Admission to the stop itself is free, which helps you feel less nickel-and-dimed right out of the gate.

Practical tip: if you want your first drink to be easy, arrive ready. Glascott’s can be loud, and you’ll be standing with the group while the tour gets rolling.

Lincoln Park in motion: Dillinger lore and spooky corners along the route

After the first bar, you’re walking through the neighborhood with stop-and-story moments that make the route feel like more than just between-pubs travel.

One highlight along the way is Lincoln Park’s spooky history, explained through specific local details rather than vague “something happened here” storytelling. You’ll also hear about the ghost of John Dillinger tied to the alley beside the theater along the route. It’s the kind of detail that makes you look at a side street and think, okay, this place has always had a second life.

This is also where a lot of the tour’s personality shows up—guides like Katie, Lara, and Mallory (plus others mentioned in guide feedback) tend to keep you moving while building suspense. You get the best results when you’re willing to slow down, listen, and accept that the walking is part of the show.

Lilly’s Bar: haunted residents and another chance to settle in

Your tour ends at Lilly’s Bar, 2515 N Lincoln Ave, but you’ll visit Lilly’s during the tour as well for a drink and another set of stories. This stop is about 30 minutes, which gives you room to breathe after the earlier pacing.

Lilly’s is presented as a place with haunted residents. That phrase matters because it signals the guide will connect the location’s reputation to the ghost lore—rather than treating the haunting like random spooky wallpaper. It’s also a nice moment for you to grab something before the last leg.

If you’re the type who likes a little social time during tours, Lilly’s is usually a good place for it. You’ll be with the group, but the tour doesn’t feel rushed.

Hook and Ladder + Halligan: secret doorway, firefighter owner, and bar history over 100 years

Stop three is where the tour turns visual and dramatic.

You’ll go to Hook and Ladder, and the tour includes Halligan, its sister bar, with a detail that makes people pay attention: there’s a secret doorway connecting them. The decor is tied to Chicago’s Fire Department, and the owner is a volunteer firefighter, which gives the storytelling an authentic local angle.

Halligan’s building has housed a bar for over 100 years, and the tour frames that long run as part of why hauntings stick around. You’ll also hear about the ghost of John Weiss, the former owner, during a drink stop.

This portion takes about 25 minutes. The main value here is how the guide uses place-based details—doorways, themes, and long-lived bar culture—to make the ghost story feel anchored, not made-up.

One thing to keep in mind: bar spaces can vary in how easy they are to hear in. If you’re sensitive to noise, position yourself so you can see your guide while you listen.

Oz Park after dark: Dorothy’s Playlot and the park that stays open late

Between pub stops, you’ll walk by Oz Park, which is one of the most charming “only in Chicago” moments on this route.

Here’s what makes Oz Park special in the tour context: it’s not just a name drop. You can find Dorothy’s Playlot, the Emerald Gardens, and character statues tied to the Oz books. The guide also points out that one of the most celebrated authors of all time, L. Frank Baum, lived about 4 miles from the park, and the park’s name ties directly to that legacy.

A practical detail matters too: the park is open until 11pm. After nightfall, you might catch the darker mood the guide hints at—this is less about jump-scares and more about the feeling of reading the place differently once the lights soften.

If you’re someone who likes photos, this is your moment. Just remember the tour is still moving, so don’t get stuck posing while the group advances.

King of Cups and the Red Lion: cocktails, tarot, and a classic haunted pub story

As you keep walking, you’ll pass King of Cups, described as Chicago’s first Spirit Lounge. The focus here isn’t just ghost lore—it’s the bar culture side.

King of Cups is known for craft cocktails, and the tour highlights that they even offer nightly tarot card readings. That’s a great pairing with a haunted tour because tarot is already part mystery, part performance. It gives your guide an easy way to connect the supernatural mood of the night to something you can actually do at the venue.

Then the tour moves to a more iconic legend: the Red Lion, one of Chicago’s most famous haunted bars. The story attached to this place is specific. The Red Lion opened in 1984 after massive reconstruction, in the former Dirty Dan’s Western Saloon. The transformation is framed as dramatic—turning a smoke-ridden, grimy rat-cemetery kind of past into a classic English pub.

The tour also says the Red Lion has multiple spirits tied to the location, which helps explain why this stop can feel more intense than the others. It’s a good capstone if you like hauntings that feel tied to a building’s long transformation.

Price and logistics: what $35.87 gets you (and how to use it well)

At $35.87 per person, the value comes from what’s included: you get a local guide plus a tour escort/host. What you don’t get is the alcohol. That’s not a dealbreaker—it just means you’re paying primarily for access to the stories and the curated bar route, not for free drinks.

Here’s how I’d think about value:

• You’re paying for a guided walk that threads together multiple venues and specific hauntings
• You’re paying for time with a guide who can interpret Chicago’s past at street level
• You’re paying for a small group experience, up to 12, which usually makes the stories feel more personal

One more practical detail: the tour uses a mobile ticket, and confirmation happens at booking time. That’s helpful because you’re dealing with a night plan and don’t want admin delays.

Also, this tour is booked about 20 days in advance on average. If you’re traveling in peak weeks, waiting too long can narrow your options.

Walking comfort, group vibe, and the 21+ factor

This tour is built for adults, and it’s listed with a moderate physical fitness level. Translation: you should expect a decent amount of walking and standing, plus the occasional uneven footing mentioned in reviews.

The good news is the tour is long enough to feel like a full night out, but short enough that you’re not committing to a marathon. Around 2.5 hours fits well for:

• first-time Chicago visits
• couples wanting a fun, different activity
• solo travelers who like meeting people without awkward icebreakers

Group size helps. With a maximum of 12 travelers, it’s less likely you’ll be stuck behind taller people the whole time or that the guide will repeat themselves endlessly.

As for vibe, most of the guide feedback centers on how engaged the group felt. Guides like Katie and Lara are frequently described as witty, enthusiastic, and the kind of storyteller who makes you feel like you’re hearing a friend’s night-plan—not a script.

The guides make the difference: Katie, Lara, Mallory, and more

This is the part you should pay attention to when you choose a night.

Across the feedback you were given, the highest praise clusters around guide performance:

• Guides that keep you laughing while still hitting real historical detail
• Guides that make it feel personalized, not generic
• Guides that connect everyone in the group so nobody feels left out

Names that show up often include Katie, Lara, Mallory, Laura, and Bobby Thomas, with other guides like Alex also mentioned. The consistent theme is style: expressive storytelling, good rapport, and pacing that works for a group.

If you’re hoping for a lively energy (not a monotone lecture), this tour is built for that. The occasional downside is when energy drops or the first stop feels too loud, which can make the start less pleasant. Still, the tour format gives the guide chances to reset the mood at later stops.

One practical idea if you’re the type who likes control: when you arrive at each bar, be clear with the group about drink ordering timing. That helps keep the storytelling flowing, especially if the space is busy.

Who should book this, and who should skip it

I’d steer you toward this tour if you want:

• a fun night walk that mixes Chicago streets with bar stories
• a tour that helps you explore Lincoln Park in a way you can actually remember
• ghost lore grounded in real locations—Prohibition speakeasy talk, firefighter-themed decor, parks tied to L. Frank Baum

I’d skip it if:

• you only want museums or quiet history
• you hate bar environments or loud rooms
• you’re looking for a fully ghost-only experience with minimal time inside pubs

This is a “street-level Chicago night” tour. If that matches your travel style, it’s easy to recommend.

Should you book Haunted Chicago Booze and Boos?

I think you should book it if you like tours that feel social, story-driven, and specific to the neighborhood you’re in. The price is fair for what you get—a guided, small-group route that turns several real bars and landmarks into a single spooky narrative.

If you want the best outcome, go in ready for a guided pub evening: bring comfortable shoes, dress for weather, and plan to purchase your own drinks. Then lean into the stories when the guide is talking—this tour works best when you let the pace carry you.

FAQ

How long is the Haunted Chicago Booze and Boos Ghost Walking Tour?

It lasts about 2 hours 30 minutes.

How much does the tour cost?

The price is $35.87 per person.

Where do I meet the tour group?

You meet at Glascott’s Saloon, 2158 N Halsted St, Chicago, IL 60614.

Do I get drinks included in the price?

No. Alcoholic drinks are not included, but you can purchase them at the stops.

Where does the tour end?

The tour ends at Lilly’s Bar, 2515 N Lincoln Ave, Chicago, IL 60614.

What’s the minimum age to join?

The minimum age is 21.

What if the weather is bad?

The tour operates in all weather conditions, but it requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.