13 Unique and Weird Chicago Tours To Experience in 2024

Are you looking for a weird Chicago tour? You’ve clicked on the right post!

Chicago is a city with a history that is often tangled with weird, and creepy legends based on real events.

From the cold-blooded murders of H.H. Holmes during the World’s Fair of 1893 to the criminal tales of Al Capone and his mob gang activity in the 1920s – these are just a few of the tales haunting the streets of Chicago, still today.

As someone who has studied in Chicago, has explored the city in the past 10 years, and cannot deny a good ghost tour, I will share with you some of the top weird Chicago tours for those of you looking for a spooky activity to do at night in the city.

So if you’re ready to jump into all things weird Chicago, let’s get started!

13 Unique and Weird Chicago Tours To Experience in 2024

Best Weird Chicago Walking Tours

1. Gangsters and Ghosts Tour in Chicago

⭐️ Rating: 5/5 Stars |  ⏳Tour Length: 2 hours | 🏛️ Check Tour Date Availability

Get to know one of Chicago’s most infamous gangsters, Al Capone, as you venture through his old stomping grounds of the city – The Loop district.

The Gangsters and Ghost Tour in Chicago has the perfect mix of history and spooky stories.

Revisit some of the now haunted places that Al Capone used to frequent, from the Congress Hotel to the Palmer House, as you listen to the guide paint the picture of the 1920s prohibition era in Chicago.

“Braeden was an awesome tour guide!! His storytelling was excellent, he was so funny, and connected with the group! The tour was so interesting and memorable. Definitely recommend!“

read reviews here

👻 Click here to book the Gangsters and Ghost Tour in Chicago

2. Windy City Ghosts: Hauntings of Chicago

⭐️ Rating: 4.5/5 Stars |  ⏳Tour Length: 1 hour | 🏛️ Check Tour Date Availability

Explore outside of the Loop District, and head north to the historic and haunted Lincoln Park neighborhood to hear some creepy tales and legends.

The Lincoln Park neighborhood is known for quite a few ghost stories, from Al Capone to haunted pubs where murders happened, mental asylums, and the inhumane practices that happened there, just to name a few.

Roam the streets after dark with your knowledgeable and local guide, and keep an eye out for a few of the ghost sightings, regularly reported by local neighbors!

“Great experience with spooky historical background! Vivid storytelling by our guide, Particularly liked the story about the Golden Dagger Tavern!”

read more reviews here

👻 Click here to book the Windy City Ghosts: Hauntings of Chicago Experience

Best Chicago Ghost Bus Tours

3. The Devil in the White City: A Haunting History Tour

Have you heard about the infamous Devil in the White City story? I won’t spoil it too much for you, but let’s just say it’s a tragic story of a series of murders that happened in Chicago during the World’s Fair of 1893.

The culprit? H.H. Holmes.

On this H.H. homes walking tour (with bus) in Chicago, you’ll learn deeply about one of the most horrendous serial killers to walk Chicago’s streets.

You’ll explore some of the sights where H.H. Holmes victims met their untimely fate while visiting the site where the Chicago World’s Fair took place, south of the city.

A tour that blends history and downright chilling stories, this tour is a perfect day activity, exploring Chicago’s Jackson Park.

“Tony the guide !!!! The guide knew his information so well. He spoke with meaning and belief. His ability to tell stories was fascinating. We saw things of Chicago we had never seen before.”

read more reviews here

👻 Click here to book The Devil in the White City: A Haunting History Tour

4. Untouchable Tours Chicago’s Original Gangster Tour

Take this almost 2-hour bus tour to explore the main hang-out spots of some of the most infamous gangsters that Chicago has ever known.

On this specific ghost tour, you’ll be entertained by the comedy and entertaining stylings of the tour guides dressed in 1920s clothes!

The tour passes through approximately 10 different stops.

Throughout the tour experience, you’ll also be entered to win a prize based on how well you remember the spooky facts, so make sure you pay attention if you want to win!

If you are traveling to Chicago during winter time, or on a rainy day, this tour is perfect to explore the city, while keeping warm.

“My husband and I had been to Chicago many times so we were looking for something different to do. the mob and gangster tour did not disappoint. Our guide (“Shoulders”) was dressed up as a gangster, was interesting, lively and engaged. We would definitely recommend this tour.”

read more reviews here

👻 Click here to book the Untouchable Tours Chicago’s Original Gangster Tour

5. Chicago Night Crimes Bus Tour

On this slightly longer mobster and crime tour throughout the Windy City, you’ll be checking out some of the hot spots where Al Capone was rumored to have frequented alone and to meet with other infamous Chicago gang members.

Visit some of the restaurants (that are still running today) like the Burwood Tap and Harry Caray’s Italian Steakhouse.

Learn about the importance of these now Chicago landmarks, and even make plans to return the next day for a meal!

The tour takes place on a bigger and more comfortable tour bus, where you’ll also be shown footage of some of the landmarks back then, as well as some little-known facts about Al Capone.

In the end, you may be quizzed on the facts, in which winners will win a prize and also earn bragging rights!

“What an amazing tour! My boyfriend and I learned a lot and we had a blast. I would highly recommend this to anyone visiting Chicago. Our guide was funny, informative, and worked at a great pace. He got everyone involved and it was just AWESOME! 10/10!!!”

read more reviews here

👻 Click here to book the Chicago Night Crimes Bus Tour

6. Chicago Crime and Mob Bus Tour

Get your dose of weird history when you book the Chicago Crime and Mob Bus Tour!

For those that are into mystery and history, this tour will certainly not disappoint.

Leaning more on history, this tour will cover not only the places where Al Capone visited during his criminal control over the Windy City but also the happenings.

Learn why Al Capone frequented Holy Name Cathedral and the Biography Theater, among other interesting places.

This Chicago mystery tour is guided by a local and experienced tour guide, who knows their stuff, and shares information and facts in a lively, and exciting way!

“Maddie’s an excellent tour guide, very informative, interesting. Learned far more than I thought I would. Now I’ll have to ask for a Chicago handshake next time I go to a bar in Chicago!”

read more reviews here

👻 Click here to book the Chicago Crime and Mob Bus Tour

Best Private Chicago Tours

7. Private Al Capone Gangster Tour in Chicago

If you’re set on wanting to explore Chicago’s most notorious sights on a private tour, consider looking into the Private Al Capone Gangster Tour!

You’ll come across some of the crime scenes that tainted Chicago’s history in the 1920s prohibition era, while also learning about some of the creepy ghost sightings and mysterious stories that take place throughout Chicago, according to locals.

The beauty of booking your own private tour is that you get to customize it to your time and taste.

The experienced tour guides will accommodate your requests as far as what sights you’d like to see and of course answer all your questions.

Booking a private Chicago mystery tour may be the best option for you if you’re traveling with a family or a larger group of people. The tour will then be opened for customization by request.

“Excellent in every way. Our tour guide Stefan & Driver Alex were very knowledgeable & accommodating. Highly Recommend”

read more reviews here

👻 Click here to book the Private Al Capone Gangster Tour in Chicago

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8. Private Haunted History of Chicago Ghost Tour

Enjoy a route through 1920s Chicago, and discover some of the dark crimes that took place back then.

This private tour of haunted history in Chicago goes in depth by visiting 3 important historical sights in the city that were key locations in Al Capone’s criminal work.

Visit Murder Castle, Death Alley, and the infamous and very haunted Congress Hotel.

The beauty of this tour is that because it’s private, you’ll be picked up directly from your hotel. You also won’t have to worry about finding the meet-up point, or running late from sightseeing all over the city.

Just make sure to confirm your hotel pick-up to make sure no problems arise! Your guide will eagerly work with you.

“Great tour telling some of the sad stories in Chicago’s history. My 13 year old grandchildren loved it. Well done. Adam was a great guide!”

read more reviews here

👻 Click here to book the Private Haunted History of Chicago Ghost Tour

Mystery and Weird Night tours in Chicago + bikes, segways, bar hopping

9. 2-Hour Haunted Segway Tour of Chicago

Roam the haunted streets of some of Chicago’s historic neighborhoods on a fun segway tour!

Meet up with your lively and knowledgable tour guides (who will come dressed in costume) and together you’ll depart into the darkness of some of Chicago’s worst crimes, stories of murderers.

As a group, you’ll learn about H.H. Holmes and his killings in 1893, as well as pass-through Al Capone’s stomping grounds in the 1920s.

Stop by the sights of where the Great Chicago Fire of 1871, to hear about what caused this devastating loss, and what came of it afterward.

Even if you’ve never ridden a segway, this tour is perfect for beginners so rest assured you’ll be safe. A helmet and a brief training are included in the tour.

“We absolutely loved our Haunted Segway Tour! Our guide, Carrie was really hilarious and made our tour truly memorable. Segway is definitely the best way to see the large variety of interesting sights throughout the city! Such a blast! Highly recommend!!”

read more reviews here

👻 Click here to book the 2-Hour Haunted Segway Tour of Chicago

10. Fright Hike: Chicago Halloween Bike Tour

Get to know some of the vicious and historical figures that took hold of Chicago for years, from the murderer H.H. Holmes and the horrendous ways he killed his victims, to the creepy legend of “Ressurection Mary” and other creepy sightings of ghost apparitions.

You’ll be led by an entertaining tour guide, dressed in costume to really elevate the fun, while you learn about Al Capone’s era in Chicago during the prohibition era.

The other fun part about this tour is that you’ll be discovering all this on a bike!

You’ll be able to see more in less time, as well as have an excuse to roam the streets of Chicago at night for incredible sights of the city’s skyline illuminated at night.

“Great all round scenes of Chicago, lakeshore, city streets, under the L, around museums. The ghost stories were very informative and fun. I highly recommend it and I’d do it again!”

read more reviews here

👻 Click here to book the Fright Hike: Chicago Halloween Bike Tour

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11. Haunted Chicago Ghost and Pub Walking Tour

Booze and ghosts – what a great pairing!

On this Chicago weird tour, you’ll be visiting some of the bars in Chicago that for one reason or another have experienced years’ worth of paranormal activity. Enough to make it onto this haunted bar-hopping experience!

Chicago is a bar city, and it always has been.

Even during the prohibition era, the city had tons of speakeasies under the radar. This was great for the bar hoppers, however, when things got out of hand, a lot of those murders and disappearances also went under the radar for a long time.

Today, many of these bars are home to many souls without direction and have made themselves known to bar employees and patrons in the past.

So if you’d like an encounter with one of these lost souls, join this exciting haunted pub walking tour!

“Took the tour with my brother while visiting Chicago .. MEGAN IS AMAZING !! Funny knowledgeable , friendly and great with the history of the area!! I would def recommend this tour as it’s so fun and interesting way to see the city !!! We learned so much !!!”

read more reviews here

👻 Click here to book the Haunted Chicago Ghost and Pub Walking Tour

12. Lincoln Park Hauntings Ghost Investigation Tour

Go on a ghost hunt with a real paranormal investigator, on one of the best tours in Chicago!

Explore the different corners of one of the most haunted neighborhoods in Chicago – Lincoln Park.

Visit sights like the:

• Suicide Bridge
• City Cemetary
• The Valentine’s Day Massacre site

Learn about the historic sight where the Great Chicago Fire of 1871 happened, and what even caused the fire to start.

When you stop by the cemetery, your paranormal investigator guide will whip out their ghost-hunting equipment for you all to use, and see what you pick up on.

Learn ghost-hunting pointers and listen to creepy ghost encounters from locals as well as your guide.

“We had such a great experience! Our tour guide, Tony, was extremely knowledgeable of the area and the history of the area. Had a decent amount of paranormal activity happen during the tour. I will definitely go on more tours related to this! Be prepared to do lots of walking!”

read more reviews here

👻 Click here to book the Lincoln Park Hauntings Ghost Investigation Tour

More weird tours in Chicago

13. Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

Add the Medieval Torture Museum to your list of Weird Chicago history tours!

Learn about the creepy and downright torturous ways in which people were executed during the Medieval times, using actual dummies inside the torture devices for an extra dose of the torturous “reality” that people endured back then.

Learn all about the gory details of what each torture device did to its victim, and what a victim did to be executed this way.

The tour is self-guided using the ghost hunting app, which you’ll get at the time of booking.

It’s the perfect way to see the museum for those who like to take their time observing each exhibit!

For these reasons, this experience is one of the best tours in Chicago.

“This place did not disappoint!! It was awesome. The staff was amazing and helpful. It was so much better than expected. The displays were perfect and informative. The interactive ones were the best.”

read more reviews here

👻 Click here to book the Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

What Crime Tours in Chicago are 1 hour or less?

Though there are no current ghost tours in Chicago that are less than 1 hour, you can check out the Windy City Ghosts: Hauntings of Chicago.

This tour is 1 hour exactly and takes place in Lincoln Park, which is perfect because it covers a little bit of everything. From haunted sights, cemeteries, and even pubs!

What are the best Crime Tours in Chicago?

With the history that Chicago has with gangster mob activity and the tumultuous times of the prohibition era, some of the best Chicago mystery tours are the bus tours like the Chicago Night Crimes Bus Tour, and the Chicago Crime and Mob Bus Tour.

They cover many of the sights you’d see on the walking tours, just with the comfort of riding on a bus.

This is especially a great option if you’re traveling to Chicago during the winter!

Other unique tours in Chicago worth exploring:

The Wrap-Up: 13 Unique and Weird Chicago Tours To Experience in 2024

I hope that this guide has helped you see the different options there are to explore some of Chicago’s weird and creepy sights with scary legends.

My top pick would have to be the Gangsters and Ghosts Tour in Chicago simply because you cannot leave Chicago without learning about Al Capone’s tremendous impact on Chicago and pop culture around the world!

This man ran a multi-million dollar operation under the radar during one of the most limiting times in U.S. history, and without remorse executed anyone who got in his way.

Many have taken inspiration from this infamous person to create books and movies, one of them being Scarface.

To recap here are the 13 unique and weird Chicago tours:

1. Gangsters and Ghosts Tour in Chicago
2. Windy City Ghosts: Hauntings of Chicago
3. The Devil in the White City: A Haunting History Tour
4. Untouchable Tours Chicago’s Original Gangster Tour
5. Chicago Night Crimes Bus Tour
6. Chicago Crime and Mob Bus Tour
7. Private Al Capone Gangster Tour in Chicago
8. Private Haunted History of Chicago Ghost Tour
9. 2-Hour Haunted Segway Tour of Chicago
10. Fright Hike: Chicago Halloween Bike Tour
11. Haunted Chicago Ghost and Pub Walking Tour
12. Lincoln Park Hauntings Ghost Investigation Tour
13. Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

Whether you’re planning a Chicago vacation in the winter (learn how to bundle up for Chicago winter because it’s no joke!) or it’s your first time in Chicago and you’re looking for things to do, a ghost tour in Chicago will never disappoint.

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