Five Great Ghost and Halloween Tours in Chicago this Season

Here’s a list of some of the best ghost and Halloween tours in Chicago for you to enjoy. If you want to get out and have some fun in outdoor Chicago, then October is basically your last, best chance. Fortunately, October is also the spookiest time of the year.

halloween tours in chicago curious cruise
Image via Mysterious Chicago

#1. Haunted History Tour

If you want to see a wilder side of the Windy City, then Weird Chicago is always a safe bet. Their signature Haunted History Tour explores stories of murder, ghosts, gangsters and more. It’s a three-hour bus tour that winds to spots all across the city. You even get to step off the bus and explore some of the infamous sites. Already been on the Haunted History Tour? Other outings cover grisly the grisly history of Chicago’s gangsters and the murder mayhem of the “Devil in the White City.” Regardless of which one you pick, Weird Chicago is a consistently popular choice for Halloween tours in Chicago.

Halloween tours in Chicago absolutely chicago segway tours haunted segway tour
You’ll have a spooky good time on Absolutely Segway’s haunted Segway tour. Image via Absolutely Chicago Segway Tours.

#2. Haunted Segway Tour

The team at Absolutely Chicago Segway Tours are an awesome crew, so I have no qualms recommending their outing. Absolutely Chicago Segway Tours says they have the world’s first haunted Segway tour, which I have no reason to doubt. You’ll visit some familiar sites, like Buckingham Fountain, and the grislier ones, like the so-called “Death Alley” between State and Dearborn. Based on our tour experience, you’ll have an awesome time learning to drive a Segway and then scooting around town. Tell ’em Detours sent ya!

#3. Atlas Obscura

Our friend, Adam Selzer, is teaming up with the awesome website Atlas Obscura for two spooky tours running in downtown this October. Adam is a prolific researcher and author who has written extensively on the gruesome side of Chicago’s history. He brings that expertise, along with the professional presentation from his podcast, Mysterious Chicago, and numerous TV appearances, on these outings. The Curious Cruise is a 90-minute trip up and down the Chicago River on the Summer of George. While you enjoy the after-dark sights, Adam will relate the stories of mysterious submarines, awful disasters, and more.

Tour guide Leyla sold-out her “Dead in Chicago” walking tour, so she has added another date for Monday, October 30. You’ll get all kinds of bloody details on true, gruesome stories of untimely deaths in the Loop.

The Devil Downtown Tour, also done by Adam through Atlas Obscura, is a walking exploration of sites associated with H.H. Holmes, the infamous devil in the White City. He’s most famously associated with the South Side. His murder castle was in Englewood and the World’s Columbian Exposition, of course, was in Jackson Park. But most of those locations are gone. So, much like our 1893 World’s Fair Tour, to see the spots Holmes would have haunted you have to explore downtown.

halloween tours in chicago adam selzer mysterious chicago
Adam Selzer may be the city’s leading authority on the spookier side of Chicago history. Image via Mysterious Chicago

#4. Mysterious Chicago

If you want to take one of Adam’s tours, but have a deep fear of Atlas Obscura caused by a mysterious accident, then have no fear! His company, Mysterious Chicago, has even more great Halloween tours in Chicago. Their signature tour, “Ghosts of Chicago,” runs on Friday and Saturday nights this month. Adam’s conducted this tour over 1,000 times since he launched it in 2005. The spot that most intrigues me is the old city jail and gallows. The building, which is where the Leopold and Loeb murder trials were held, just looks incredibly haunted.

#5. Haunted Hyde Park

Another friend of ours, Greg Fairbanks, has been getting rave reviews since he started Hyde Park Chicago Tours a few years ago. His Haunted Hyde Park Tour runs at twilight and explores the iconic neighborhood’s stories or murder and mayhem. While strolling through the beautiful environs of the University of Chicago, you’ll learn about infamous criminals like H.H. Holmes, Leopold and Loeb, and the Lipstick Killer. This tour is only running at 5:30pm this Friday, Saturday, and Sunday.

I’m probably going to be too busy leading our own architectural walking tours to get out and enjoy all of these Halloween tours in Chicago this year. But I hope we sparked your interest in some of the ghoulish fun to be had this October. Happy hauntings!

– Alex Bean, Content Manager and Tour Guide

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Ellen

Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”
Robert
GetYourGuide

Jen

Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”
Heather
TripAdvisor

Elyse

Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.

Anthony

Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.

Marie

Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”
Lorit
TripAdvisor

Sonny

Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K
TripAdvisor

Alex

Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K
Yelp

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F
Yelp

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