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 2016, 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:

  • The Haunted History Trolley Tour (October 25) a 21+ older trolley tour that tells tales of of John Dillinger's death, the Devil Baby of Hull-House and the ghosts of Lake Michigan
  • Garden of the Dead (October 27) 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 after-hours cemetary tours at Bohemian National Cemetery on (October 23, November 6) and Graceland Cemetery on (October 29-31)

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 will weaving in tales of supernatural occurrences and infamous figures (October 1-30 Fridays-Sundays).

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 Hustletown will come to life on the kayak tour offered by Wateriders (October 21-23).

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) 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 two weeks of October). 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 28-29), where tales of strange sounds, unexplained sightings, and untimely endings are lurking around ever corner!

Another walking option, Death, Disease and Bones: The Lincoln Park Walking Tour (October 20, 22, 27) follows historian Sally Sexton Kalmbach through the macabre history of the vast, windswept burial site.

Another neighborhood gets in on the Halloween action this year with a special, ages 21+ editon of their tour. Bizarre Bucktown Halloween Tour (October 28, 29, 31) 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. Then 110 minutes later the tour concludes at neighborhood bar 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 thirteen — lucky number! — different vignettes.

If you choose to stay downtown, and there's enough haunted happenings there 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 1900's Red Light district, and learn about downtown prison breaks.

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