Haunted Chicago Booze and Boos Ghost Walking Tour
Enjoy a memorable Chicago experience on this haunted pub tour. Your costumed guide, dressed as a Flapper or 1920s Gangster, will lead you on a mile-long journey while telling spooky stories of forgotten cemeteries, lingering spirits, and more. Stop at three different bars for drinks (at own expense) as you learn the secret tales behind Chicago’s haunted past.
Overview
Enjoy a memorable Chicago experience on this haunted pub tour. Your costumed guide, dressed as a Flapper or 1920s Gangster, will lead you on a mile-long journey while telling spooky stories of forgotten cemeteries, lingering spirits, and more. Stop at three different bars for drinks (at own expense) as you learn the secret tales behind Chicago’s haunted past.
Itinerary
Lincoln Park
You'll meet your tour group here to begin stories and grab a drink. Glascott's has been family owned for four generations. The building was originally a meat market, but during Prohibition, it was known as “James Morley Soft Drinks” and operated as a speakeasy. Your costumed guide will tell you all about it!
25 minutesLincoln Park
Explore the spooky history of Lincoln Park!
Biograph Theatre
Hear all about the ghost of John Dillinger that haunts the alley beside the theater!
Lilly's
Stop in for a drink and hear about their haunted residents.
30 minutesHook and Ladder, and its sister bar Halligan, have a secret doorway connecting them. The owner is a volunteer firefighter, and the decor is in honor of Chicago’s Fire Department. The building that houses Halligan has been a bar for over 100 years! You'll hear all about the bar and its ghostly former owner, John Weiss, when we stop in for a drink.
25 minutesOz Park
Along the tour route, we'll walk by Oz Park. Did you know that one of the most celebrated authors of all time lived about 4 miles from here? L. Frank Baum, author of the beloved Oz books, is the namesake for this quaint park where you can find Dorothy’s Playlot, the Emerald Gardens, and character statues of the books!
The park is open until 11pm, and after nightfall, you might just run into some of its ghostly inhabitants.
Along our route, we'll pass by Chicago’s first Spirit Lounge, King of Cups. This is a place that definitely appreciates spirits of any variety, with craft cocktails and a few hauntings of its own. They even offer nightly Tarot Card readings!
A few strange happenings have convinced employees that some otherworldly patrons have adopted the gothic bar as their regular watering hole...
Along our route, we'll stop outside of one of the most famous haunted bars in Chicago and reveal its stories.
The Red Lion opened in 1984, after massive reconstruction, in the former Dirty Dan’s Western Saloon. The place was transformed from a smoke ridden, grimy rat cemetery into a classic English pub. It has multiple spirits that are seemingly tied to the location.
Location
Address
2158 N Halsted St, Chicago, IL 60614, USA
Experience
Highlights
Inclusions
- Local guide
- Take-home commemorative can cooler or cup!
- Tour escort/host
Exclusions
- Alcoholic drinks (available to purchase)
- Gratuities
Additional Information
- Travelers should have at least a moderate level of physical fitness
- Minimum age is 21 years
- Operates in all weather conditions, please dress appropriately
- Minimum of 2 adults to book
Guide Languages
English
Cancellation Policy
A full refund will apply if you cancel more than 24 hours before the activity start time.
No refund is possible if you cancel less than 24 hours before the activity start time.
Related Attractions
Explore similar attractions that other travelers have enjoyed. Discover more options to enhance your travel experience

Walkin' with Colin: Chicago Tour du JourWalkin' with Colin: Chicago Tour du Jour
Embark on a profound, downtown walk-around led by an "...entertaining, informative and enthusiastic!" guide on a mission to share the most sensational sights, stories and secrets of the Windy City! During our loop around "Da Loop" our group will pee...
$39
per adult
Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and BeerFun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer
Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and combine it...
$179
per adult
Gold Coast Self-Guided Smartphone Audio Walking TourGold Coast Self-Guided Smartphone Audio Walking Tour
Delve into the rich history and notable architecture of one of Chicago’s most luxurious neighborhoods—and learn insider stories as you go—with this self-led smartphone audio walking tour. Upon booking, download the app and set off at a time a...
$6
per adult

Customizable Private Chicago Scenic Driving TourCustomizable Private Chicago Scenic Driving Tour
Chicago is a very big city with a lot of activities & sightseeing to do. To tour the city quickly, it requires the help of a knowledgeable local driving guide. That's where I step in to assist you. Your Private Chicago Scenic Driving Tour will start...
$281
per adult

The Art Institute of Chicago: Skip The Line Ticket + Exclusive Guided TourThe Art Institute of Chicago: Skip The Line Ticket + Exclusive Guided Tour
Prepare for an enriching experience at The Art Institute of Chicago. With an impressive collection of 300,000 art pieces, this institution is a treasure of creativity and talent. This small group tour is here to guide you through the highlights of ar...
$74
per adult
Chicago Scavenger Hunt and Highlights Self-Guided TourChicago Scavenger Hunt and Highlights Self-Guided Tour
Use clues at each attraction to find your next destination and challenge yourself to use logic, imagination, observation, and team spirit to complete the game. Uncover local information and facts about the city as you explore. Discover hidden...
$13
per adult
Interior Architecture Walking Tour Inside the LoopInterior Architecture Walking Tour Inside the Loop
Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco sp...
$35
per adult
2-Hour Chicago Lakefront & Museum Campus Segway Tour2-Hour Chicago Lakefront & Museum Campus Segway Tour
Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and ...
$64
per adult
Lakefront, Museum Campus Small-Group Segway TourLakefront, Museum Campus Small-Group Segway Tour
Experience Chicago in a new way on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths of Grant Park to the famous Buckingham Fountain. Then, tra...
$64
per adult
Art Institute of Chicago Guided Tour and Skip the Line TicketArt Institute of Chicago Guided Tour and Skip the Line Ticket
Make the most of your time at the Art Institute of Chicago by avoiding the crowds to get in. Whether you’re an art aficionado or beginner, this opportunity lets your learn about the museum and its pieces through the eyes of an art historian g...
$74
per adult
Chicago Murder Mystery and Sightseeing Walking TourChicago Murder Mystery and Sightseeing Walking Tour
Bored of traditional walking tours? Try an experience that mixes sightseeing with an engaging game in this murder mystery tour through Chicago. Play as a detective and a suspect as you wander through various neighborhoods and see the city. Le...
$35
per adult
Art Institute of Chicago Small-Group Highlights TourArt Institute of Chicago Small-Group Highlights Tour
Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat...
$90
per adult
Downtown Chicago Architecture, Art, and History Walking TourDowntown Chicago Architecture, Art, and History Walking Tour
This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about ...
$33
per adult
West Side Neighborhoods Foodie Small-Group Bike TourWest Side Neighborhoods Foodie Small-Group Bike Tour
Make your way to Chicago's Streeterville neighborhood near Navy Pier to meet your guide and group. Get set up with your helmet and bike, then pedal off through the River North neighborhood, across the Chicago River, and over to Fulton ...
$99
per adult
Chicago Small-Group Digital and Polaroid Photo ShootChicago Small-Group Digital and Polaroid Photo Shoot
Don’t leave Chicago without taking home professional digital and polaroid shots of your visit. Starting from the iconic Millennium Park, your photographer guide takes you to some of the city’s most photogenic landmarks to take photos of you t...
$169
per adult
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline CruisePrivate Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
Enjoy a private two and a half hour sailing experience for up to four people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make...
$488
per adult
Chicago Lake Michigan Private Sunset Sailing CharterChicago Lake Michigan Private Sunset Sailing Charter
Soak up unbeatable views of Lake Michigan and the Chicago skyline—and stay on the water long enough to watch the lights come on in the city—on this private, sunset sailing tour. This charter is completely customizable, giving you the chance t...
$508
per adult
Historical and Architectural Chicago Fireboat River/Lake CruiseHistorical and Architectural Chicago Fireboat River/Lake Cruise
Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in between! Our flagship vess...
$45
per adult
Lincoln Park Hauntings Ghost Investigation TourLincoln Park Hauntings Ghost Investigation Tour
Arrive at Lincoln Park after dark, leaving room in your day to complete other activities on your itinerary. Join forces with your personal paranormal investigator and begin to take a leisurely stroll through the neighborhood.Delve into...
$40
per adult
Chicago River Architecture Cruise History and Sightseeing TourChicago River Architecture Cruise History and Sightseeing Tour
Make your way to either Navy Pier or Michigan Avenue (depending on option chosen) for your cruise departure. Board your riverboat and find a comfortable seat; a restroom is available on the boat. Listen as your guide, an architecture e...
$49
per adult

45-Minute Private Helicopter Flight for 1-3 People45-Minute Private Helicopter Flight for 1-3 People
Enjoy spectacular views of Chicago from an MD500 helicopter. This helicopter flight over Chicago covers all the important highlights of the city from McCormick Place and Soldiers Field in the South to Wrigley Field in the North. Depart from Schaumbu...
$756
per adult
Architecture cruise in Spanish on the Chicago River from Michigan AveArchitecture cruise in Spanish on the Chicago River from Michigan Ave
This picturesque cruise is led by a professional Spanish speaking guide who shares exciting details and the historical significance of the buildings that line the Chicago River. Boarding at the dock on Michigan Avenue, you'll sail down all th...
$54
per adult
Chicago American Writers Museum Skip-the-Line Admission TicketChicago American Writers Museum Skip-the-Line Admission Ticket
Immerse yourself in American literary traditions, and enjoy a wide range of interactive exhibitions, during a visit to Chicago’s one-of-a-kind American Writers Museum. Conveniently located on Michigan Avenue, the museum was established in 201...
$16
per adult

The Art Institute of Chicago: Fast PassThe Art Institute of Chicago: Fast Pass
Home to some of the world's most recognizable artworks, the Art Institute of Chicago is America's second-largest art museum. Seeing famous art at the Art Institute of Chicago is a reliable way to ensure your day in the Windy City is nothing short of ...
$40
per adult
The Art Institute of Chicago: Fast PassThe Art Institute of Chicago: Fast Pass
Home to some of the world's most recognizable artworks, the Art Institute of Chicago is America's second-largest art museum. Seeing famous art at the Art Institute of Chicago is a reliable way to ensure your day in the Windy City is nothing s...
$40
per adult
Chicago History Museum: Entry TicketChicago History Museum: Entry Ticket
Explore the history of Chicago and United States through permanent and temporary exhibitions drawn from more than 20 million items in the Chicago History Museum. Showcasing photography, documents, artifacts, and interviews, the permanent and ...
$17
per adult

Chicago CityPASS®: Save up to 49% at 5 Top AttractionsChicago CityPASS®: Save up to 49% at 5 Top Attractions
Experience 5 must-see attractions and save up to 49% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your tickets, you’ll have plenty of ti...
$126
per adult

American Writers Museum Flexible Date Entry TicketAmerican Writers Museum Flexible Date Entry Ticket
Learn about the history of writing and how it has shaped American culture with a ticket to the American Writers Museum in Chicago. Stroll through exhibits that appeal to all 5 senses, explore the intricacies of language through games, and write your ...
Go City | Chicago All-Inclusive PassGo City | Chicago All-Inclusive Pass
Welcome to the windy city! Home to world-famous art museums, iconic architecture and delicious food, Chicago is a perfect blend of midwestern hospitality and dynamic urban metropolis all set against the beautiful backdrop of Lake Michigan. Do...
$139
per adult

Color Factory Chicago General Admission TicketColor Factory Chicago General Admission Ticket
Voted the #1 Immersive Art Experience in America by USA Today readers in 2024, Color Factory Chicago celebrates the joy of color. Embark on a bright and colorful journey through 14+ immersive installations that inspire joy and human connection, expa...
$32
per adult
360 Chicago Observation Deck: Skip The Line Entry Ticket360 Chicago Observation Deck: Skip The Line Entry Ticket
It might be called the Windy City but from the 94th floor of downtown Chicago's John Hancock Center, you'll see a lot more than windswept trees. 360 Chicago offers incredible views of the city and Lake Michigan, plus four neighboring states. ...
$30
per adult

Willis Tower Skydeck and The Ledge TicketWillis Tower Skydeck and The Ledge Ticket
Enjoy an unrivaled view over the city of Chicago on a trip up the city's Willis Tower. This famous building, once known as the Sears Tower, is not only home to a Skydeck on the 103rd floor, but it also features The Ledge, a series of 4 glass-paneled ...
$29
per adult

Navy Pier Centennial Wheel TicketNavy Pier Centennial Wheel Ticket
Experience the views from the Centennial Wheel at the Historic Navy Pier in Chicago with this attraction ticket. Be suspended over Lake Michigan at the mouth of the Chicago River. Marvel at the Chicago skyline and gaze out over the sparkling waters o...
$20
per adult

360 Chicago Observation Deck Fast Pass Ticket360 Chicago Observation Deck Fast Pass Ticket
Travel to the 94th floor of the former John Hancock Center in just 40 seconds on one of North America’s fastest elevators. Step foot onto the observation deck to experience breathtaking views of the Chicago Skyline and Lake Michigan. Take in the cit...
$49
per adult

360 Chicago Observation Deck Sip and View Ticket360 Chicago Observation Deck Sip and View Ticket
Take in the beautiful views of Chicago as you enjoy a drink from our carefully curated Sip menu. 360 CHICAGO Observation Deck sits 1,000 feet over Chicago’s legendary Michigan Avenue. Located on the 94th floor of 875 N. Michigan (formerly the John Ha...
$39
per adult

Chicago Skyline PassChicago Skyline Pass
From stuffed pizza crusts to windswept walks, Chicago is one American city that wants to entertain you! This specially curated package has been designed to tick-off sky-high views and the city's best architecture from your to-do list. Get easy ac...
$120
per adult

360 Chicago Observation Deck General Admission360 Chicago Observation Deck General Admission
360 CHICAGO Observation Deck sits 1,000 feet over Chicago’s legendary Michigan Avenue. Located on the 94th floor of 875 N. Michigan (formerly the John Hancock Center), 360 CHICAGO gives you the opportunity to experience the best views of the Chicago ...
$27
per adult
360 Chicago Observation Deck Tickets360 Chicago Observation Deck Tickets
360 CHICAGO’s concourse level includes an interactive exhibit highlighting the history of Chicago and the vibrant cultures and businesses across Chicago neighbourhoods. Get inspired to explore Chicago beyond downtown after watching a short do...
$30
per adult