Skip to content

    Ghost Cities · Recommended Tour

    Fright Hike: Chicago Halloween Bike Tour

    Freaky Foot Tours doesn't sell ads. When you book through links on our site we may earn a small commission at no additional cost to you.

    Fright Hike: Chicago Halloween Bike Tour

    Pedal through Chicago’s scary heritage with a 3-hour Halloween bike tour that includes hauntings, tragedies and overflowing cemeteries. Experience the creepiest parts of the city as you follow your professional actor guides through the Halloween streets, and watch them bring Chicago’s ghosts to life. Learn about the infamous ‘Resurrection Mary,’ figure out why the Levee District is so famously haunted, and hear the story of H.H. Holmes, Chicago’s most notorious serial killer.

    This one moves on two wheels, which sets it apart from the walking and riding-in-a-vehicle formats most cities offer. Covering three hours of ground by bike lets it reach cemeteries and neighborhoods a short walk could not, so it suits people who are comfortable pedaling for a stretch and want more territory than a stationary tour. It is not the pick for anyone who cannot ride, and the subject matter, including a notorious serial killer, skews it away from young children.

    Chicago has a wide, layered dark history, and this format uses the bike to string distant stops together with actors doing the narration. Go in expecting theatrical delivery and physical activity in one package. If you want to stand still and soak in atmosphere, or if a long ride sounds like work rather than fun, a walking tour will suit you more.

    Questions people ask

    How long is the tour and how physical is it?

    It runs about three hours and is done by bicycle, so you should be comfortable pedaling for the duration and covering real distance across the city.

    Is this suitable for young kids?

    The material covers tragedies and a notorious serial killer, and it requires riding a bike for three hours, so it leans toward older kids, teens, and adults rather than small children.

    Who leads the tour?

    Professional actor guides lead the ride and perform the storytelling, so expect a theatrical delivery alongside the history.

    Check Availability & Book

    ← Explore more Ghost Cities

    The One State Where We Hold the Lantern

    Coming to Arizona? Walk with us.

    Everywhere else, we write the guide. In Flagstaff, Tucson and Prescott we lead the tour, nightly, in person, with five generations of Arizona roots behind every story.

    5.0 Google · 675+ reviews Best of Flagstaff 2023, 2024 & 2025 Locally owned · Est. 2015