Chicago
Halloween Activities

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Our most recommended Chicago Halloween Activities

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

1. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn. Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

Chicago: Ghosts of Lincoln Park Walking Tour

2. Chicago: Ghosts of Lincoln Park Walking Tour

Meet your guide at the meeting point then set off on an unforgettable walking tour through Northside Chicago. Travel back in time as you visit some of the city’s most haunted locations in the mysterious Lincoln Park neighborhood. Learn about the forgotten burial ground that forms the foundation of this bustling district. Check out the bathroom mirrors at Lincoln Park Zoo, home to the ghost of a Victorian woman in white. And, hear about the spirit that haunted Al Capone in his final days.  Throughout the tour, you’ll listen to the strange and disturbing tales of each location. On the standard tour, visit eight historic sites, or opt for the extended tour which includes 12 ghoulish locations. By the end of the tour you’ll have learned about and experienced firsthand the alternative side of Chicago.

Chicago: Wind and Souls Adults Only Guided Ghost Tour

3. Chicago: Wind and Souls Adults Only Guided Ghost Tour

Enjoy a spine-tingling walking tour learning about Chicago's gruesome and haunting past with a local guide. Hear stories about paranormal activity in the Alley of Death, a librarian's spirit that haunts a local library, the ghost of Al Capone, and a hotel that is said to have inspired Steven King. Begin your tour at The Chicago Theater and hear the tragic story of how 602 people lost their lives at the Iroquois Theater in the 1903 fire. Continue walking to the nearby James M. Nederlander Theater and learn about the paranormal activity in the Alley of Death. Move on to the Chicago Cultural Center to hear about Frederick H. Hild, the second librarian in the history of Chicago's public library system, who is claimed to be haunting the local library.  Walk to nearby Lincoln Park and understand why it's considered to be more of a burial ground than an actual park. You will then stop by The Art Institute of Chicago and discuss how more than 300,000 items are considered to be haunted.  Then it's time to visit Congress Triangle Garden to view the Congress Plaza Hotel. Considered to be one of the most haunted hotels in the country, Congress Plaza Hotel is said to have served as a source of inspiration for a short story written by Stephen King. Complete your tour at the Exchequer Restaurant and Pub, where you will hear about Al Capone's dark past, and how people claim his ghost haunts the entirety of Chicago.

Chicago: Family Friendly Ghost Walking Tour with Local Guide

4. Chicago: Family Friendly Ghost Walking Tour with Local Guide

Perfect for families, friends, or a combination of both, enjoy a spooky evening learning about Chicago's haunting past on a walking ghost tour with a local guide. Hear stories about America's first serial killer, the Devil Baby of Hull-House, and a hotel that is said to have inspired Steven King. Begin your tour at Cloud Gate, known as The Bean, to meet your guide and receive an introduction to the tour. Make your first stop at the Flying Dragon to hear about the Devil Baby of Hull-House, which is rumored to have inspired the film "Rosemary's Baby". Next, head over to the Chicago Stock Exchange Arch and learn about H. H. Holmes, considered to be America's first serial killer. Continue to the Abraham Lincoln statue and find out why Lincoln Park is considered more of a burial ground than an actual park. Then it's time to visit Congress Triangle Garden to view the Congress Plaza Hotel. Considered to be one of the most haunted hotels in the country, Congress Plaza Hotel is said to have served as a source of inspiration for a short story written by Stephen King. Further on your tour, learn about the Dearborn Massacre and American Gangster, John Dillinger. Conclude your tour at Buckingham Fountain to learn how the S. S. Eastland met a tragic end in the Chicago River.

Bobby's Fright Hike: Halloween Edition Chicago Bike Tour

5. Bobby's Fright Hike: Halloween Edition Chicago Bike Tour

Join Bobby’s Bike Hike as we unleash our Halloween "Fright" Hike bike tour through the city of Chicago! We’ll ride through a former cemetery where thousands of bodies are buried and visit the Chicago River site where 844 people drowned in the middle of broad daylight. It is believed that one man, Charley Porter, who was on the boat when it sunk, still haunts the area to this day. We’ll discuss Resurrection Mary, Chicago’s most infamous ghost, as well as explain some of Chicago’s most notoriously haunted locales from the Levee District to the Colombian Exposition and the exploits of the one and only H.H. Holmes.

Frequently asked questions about Chicago Halloween Activities

What are other things to do than Halloween Activities that are worth visiting in Chicago?

The other unmissable things to do in Chicago are:

Which Chicago Halloween Activities are taking additional COVID-19 precautions?

These Chicago Halloween Activities are taking additional COVID-19 precautions:

Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

4.7 / 5

based on 79 reviews

What can I say! Awesome experience. We had a great tour guide she was knowledgeable about all of Chicago and connects the ghosts' stories very well. Sometimes it feels like the ghost would come out of the buildings. We highly recommend it.

We had a great tour with Lizzie. She was great fun and had great enthusiasm. Learned a lot and thoroughly enjoyed it

Lots for fun and learned a lot about this history of Chicago- tour quide was awesome. Highly recommend it!

Sarah was an awesome guide! Very funny and knowledgeable! We really enjoyed our tour with her!

Great tour about the history of gangsters and ghosts in Chicago!