Haunted Tours for Halloween

Spooky, haunted tours filled with Chicago history and lore? Take a ride via segway or creep along on a walking tour.

There's a chill in the air and darkness cloaks the city — be brave and explore the haunted side of Halloween on Chicago haunted tours by boat, trolley, Segway or foot. All throughout October 2017, spooks and scares await on these 13 Halloween tours.

The Chicago History Museum knows a thing or two about the city's haunted past. Take your pick from their dark side of history happenings throughout the season, which include:

  • Devil in the White City Bus Tour (October 21, 2017): a tour of the notorious sites of the World's Fair Chicago serial killer H.H. Holmes
  • Garden of the Dead (October 17 & 24, 2017): a hair-raising walking tour that uncovers the hidden truths of Lincoln Park's elusive graves and the forgotten history buried in the Chicago History Museum's backyard
  • And the creepiest of all: cemetery tours at Bohemian National Cemetery (October 22, November 5, 2017) and Graceland Cemetery (October 28-29 & 31, 2017)

Seadog River & Lake Architectural Tours Return! - Image

Spirits, scandals and sins... learn all about the ties to Chicago while aboard an evening boat tour. Seadog Cruises Haunted Tours will navigate the dark waters of the Chicago River while weaving in tales of supernatural occurrences and infamous figures (October 6-31, 2017, Fridays-Sundays and Halloween).

Think you're brave enough to tackle the shadows of the Chicago River on your own? The dark waters and dark tales of Ghosts and Gangsters of Hustlertown will come to life on the kayak tour offered by Wateriders on Friday-Sunday evenings throughout October 2017.

For a boat option that is less tricks and more treats head to Navy Pier. Mystic Blue is hosting a family-friendly affair with Tricks & Treats Boathouse Lunch Cruise (October 30, 2017) to showcase the greatest skyline views our lakefront has to offer — while DJs spin Halloween jams and diners are treated to delicious bites and plenty of candy. Costumes encouraged!

Get into the spirit with a chilling nighttime outing on wheels that zips through the shadows and darkness of downtown. Both lead you deep into the world of ghouls, gangsters, disasters and unexplainable deaths:

Hop on two wheels and traverse the city via bicycle with Bobby's Fright Hike: Halloween Edition Bike Tour (offered nightly the last week of October 2017). From the former cemetery along the lakefront where thousands of bodies still remain today, to the riverside site where 844 people drowned in the middle of broad daylight, to Resurrection Mary — Chicago's most infamous ghost — your ride will cover all sorts of sights, sounds and creepy tales.

Or go by foot and walk — if you dare — through one of Chicago's most historic South Loop neighborhoods after dark. Glessner House Museum presents Shadows on the Street: Haunted Tours of Historic Prairie Avenue (October 27-28, 2017), where tales of strange sounds, unexplained sightings, and untimely endings are lurking around ever corner!

The Driehaus Museum offers another walking option called the Spooky Walking Tour (Thursdays and Saturdays, October 19-28, 2017), which follows historian Sally Sexton Kalmbach through the macabre history of a vast, windswept 19th century burial site located in Lincoln Park.

Another neighborhood gets in on the Halloween action with a special, ages 21+ edition of their tour. Bizarre Bucktown Halloween Tour (beginning on October 13, 2017 and held on October Friday-Saturday nights & October 31, 2017) explores the 'hood from an even more shocking and mysterious angle. Imagine starting outside shuttered Lincoln Tavern, the site of a brazen murder and shocking abduction. Ninety minutes later the tour concludes at neighborhood restaurant Club Lucky, which is known to have a spirit of its own. What happens between those two stops you'll have to find out yourself says tour guide Gordon Meyer, who is also a magician, but there are 13— lucky number! — different vignettes.

If you choose to stay downtown, there's enough haunted happenings to keep you occupied, Chicago Ghost Tours from Free Tours by Foot adds history and humor to the mix, too. Walk along the streets that H. H. Holmes (Chicago's first serial killer) wandered as he stalked his prey, get a glimpse of Chicago's sordid past through stories of the Everleigh Club and the 1900s Red Light district, and learn about downtown prison breaks.