Fright Hike: Chicago Halloween Bike Tour

  • Operates Seasonal - 3 hours
  • Refundable
  • Printed Voucher/E-Voucher
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Operates Seasonal
Activity Highlights
This is a typical itinerary for this product

Stop At: Bobby's Bike Hike Chicago, 540 N Lake Shore Dr, Chicago, IL 60611-3414

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!

Duration: 15 minutes

Stop At: John Hancock Center, 875 N Michigan Ave, Chicago, IL 60611-1803

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.

Duration: 15 minutes

Stop At: Chicago River, Chicago, IL

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.

Duration: 15 minutes

Stop At: James M. Nederlander Theatre, 24 W Randolph St, Chicago, IL 60601, USA

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!

Duration: 15 minutes

Stop At: The Congress Plaza Hotel & Convention Center, 520 S Michigan Ave, Chicago, IL 60605, USA

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.

Duration: 15 minutes

Stop At: Grant Park, 337 E Randolph St, Chicago, IL 60601

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.

Duration: 15 minutes

Stop At: Lake Michigan, Beaches for swimming, IL

The tour finishes with a lakeside ride back to Streeterville, passing the dark depths of Lake Michigan, home to countless deadly shipwrecks.

Duration: 15 minutes

Pass By: Navy Pier, 600 E Grand Ave, Chicago, IL 60611-3419

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!

Activity Details
Come get spooked on Bobby’s Fright Hike! Bobby’s Bike Hike is America’s longest running city bicycle company, and this is Chicago’s premiere Halloween ghost tour. Hop on two wheels and follow Bobby’s expert tour guides through some of the most paranormal and frightening spots in the Windy City. This 3-hour guided bicycle tour explores the uber-haunted John Hancock Center, the site of the SS Eastland Disaster (one of the deadliest shipwrecks in American history), the 200-year old ghosts of the Congress Plaza Hotel, and more! This is the perfect outdoor activity for anyone looking to explore Chicago after dark. Connect with your inner ghost hunter and sign up today!
Departure & Return
Departure Point540 N Lake Shore Dr, Chicago, IL 60611, USA Departure Time6:30 PM
ReturnReturns to original departure point
What's Included
  • Bicycle
  • Helmet
  • Expert local tour guide
  • Guide Gratuity, Suggested 15-20% (Venmo and PayPal available)
  • Food and drinks
  • Entry/Admission - John Hancock Center
  • Entry/Admission - James M. Nederlander Theatre
Additional Information
  • Confirmation will be received at time of booking
  • 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
  • Not wheelchair accessible
  • Near public transportation
  • Travelers should have a moderate physical fitness level
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
  • This tour/activity will have a maximum of 15 travelers
  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
  • Hand sanitizer available to travelers and staff
  • Social distancing enforced throughout experience
  • Gear/equipment sanitized between use
  • Contactless payments for gratuities and add-ons
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
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$49.99 USD
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Adult(s) upto 9 passengers
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