Fright Hike: Premier Chicago Halloween Bike Tour
5 Ratings
Embark on Bobby's Fright Hike, Chicago's premier Halloween bike tour. Explore haunted landmarks, uncover chilling stories, and connect with your inner ghost hunter. Book now!
Duration: 3 hours
Cancellation: 1 day learn more
  • Bobby’s Bike Hike Chicago - The journey begins at the Bobby’s Bike Hike headquarters in Streeterville, where you’ll meet your terrifying and fun-loving tour guide! We will outfit you with a ready-to-ride Bobby’s bicycle, complete with front and rear lights to keep the group shining bright amidst the spooky darkness. Our fleet of comfort bikes makes riding a breeze, so you can keep your focus on the frights!
  • John Hancock Center - The tour will then set out to see the John Hancock Center, home of the city’s most prolific curses and tragic demise. It’s one of the tallest buildings in Chicago and has an equally steep history of disaster.
  • Chicago River - Next, the group will cruise over to the Chicago River, site of the horrific SS Eastland shipwreck, which killed more than twice as many people as the Great Chicago Fire.
  • James M. Nederlander Theatre - From there the guide will lead you into the Chicago Loop toward the Oriental Theatre, formerly known as the Iroquois Theatre. In 1903, a horrific blaze left hundreds trapped in the burning building and the alley beside it. It is largely believed that these souls still haunt the venue, even bringing their families to a show every now and again!
  • The Congress Plaza Hotel & Convention Center - Following that, you’ll trek to the South Loop’s Congress Plaza Hotel, one of the most infamous haunted hotels in the world. Here you’ll take a break and maybe hunt for a ghost or two in the lobby. Bobby advises against venturing upstairs—multiple rooms have been sealed off for a reason.
  • Grant Park - ater, the frightening ride continues down to Grant Park and Museum Campus, two of Chicago’s most iconic waterfront parks. These centuries-old spaces are vast and haunting, the perfect place to share more ghost stories… including those of H.H. Holmes, a serial killer who preyed upon visitors to Chicago’s 1893 World’s Fair. Though his south-side murder castle has long been demolished, the spirits of his victims are still present all around.
  • Lake Michigan - The tour finishes with a lakeside ride back to Streeterville, passing the dark depths of Lake Michigan, home to countless deadly shipwrecks.
  • Navy Pier - On your way back, pass the bright facade of Navy Pier, which long stood abandoned after the Second World War, a perfect place for paranormal activity.

The tour concludes back at the Bobby’s Bike Hike headquarters after three hours and countless frights! At this point, you’ll know why Bobby’s is Chicago’s favorite company for nighttime bicycle tours!

What's Included
  • Expert local tour guide
  • Bicycle rental included
  • Safety helmet provided
What's Not Included
  • $10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
  • Food and drinks
Additional Information

Join the thrill of Bobby’s Eerie Ride! As the longest operating urban bicycle venture in the USA, Bobby’s Bike Hike brings you the foremost ghostly Halloween tour of Chicago. Mount your bicycle and allow Bobby’s seasoned guides to lead you through some of the most chilling and otherworldly locations within the Windy City. This 3-hour narrated bicycle journey ventures through the intensely haunted John Hancock Center, the location of the SS Eastland Disaster (one of America’s most catastrophic maritime tragedies), the centuries-old spirits of the Congress Plaza Hotel, and beyond! The ideal outdoor thrill for those keen to discover Chicago when the sun goes down. Unleash your inner specter chaser and register now!

  • This tour is appropriate for most ages and fitness levels. Professional guides blend quality information, group interaction, and most of all, fun, to create an unforgettable Chicago experience. Bikes are provided. Child bikes, seats and tag-alongs are available.
  • Please note: children must be strong, capable riders and be able to bike for 9 miles
  • TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
  • Operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund.
  • Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
540 N Lake Shore Dr
North Lake Shore Drive
Directions: The entrance to 540 N. Lake Shore Drive is on the south side of Ohio Street just west of Lake Shore Drive. Enter through the covered driveway and our entrance is on the right just past the Driveway. Please note: you must walk through the covered driveway, no cars and no public parking.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
(5 Ratings)
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Oct 24, 2022
Best spooky bike tour in town!! 👻 - Josie provided an entertaining, safe and spooky bike tour. Lots of laughs, spooks and adventures! HIGHLY recommend!!!!
Review provided by Viator
Oct 23, 2021
Great Chicago night out! - 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!
Review provided by Viator
Oct 15, 2021
Great guides and e-bikes! Best way to see Chicago day or night - Fantastic bike ride two days in a row- we did the architecture first then the Fright Bike - both guides were awesome- gabe and paul- highly recommended -
Review provided by Tripadvisor
Oct 17, 2017
Don't see Chicago without going on Bobby's Bike Hike - Bobby's Bike Tour Halloween Edition was the highlight of our Chicago visit. We had our 3 year old and 7 year old. The weather was drizzly, damp and cool. The roads are flat and the route was safe especially on a Wednesday night. I was especially impressed with our guide's attention to the script and genuine enthusiasm. They have ebikes which I would insist on in Atlanta or other hilly towns but it wasn't necessary even pulling kids. Also, the hike did not have people jumping out trying to scare you. It was a tour of some of the more gruesome and haunted parts of Chicago. My 7yr old had just the right fright and the 3year old wanted to keep riding in her Yepp seat around town to see the pretty lights :D
Review provided by Tripadvisor
Oct 17, 2017
Amazing Bike Ride and Haunting Update - Mark was great! The bike ride was awesome, very safe and fun. Mark knew his Chicago haunting history and shared some very exciting stories with us. Would recommend Bobby's Bike Tour's anytime and hope to make it back to the Windy City to do it again!
Review provided by Tripadvisor