Fright Hike: Chicago Halloween Bike Tour

2 Ratings
  • Live Guide
  • Instant Confirmation
  • E-Ticket
  • 3 hr

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!

Itinerary Details

This is a typical itinerary for this product

Stop At: 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!

Duration: 15 minutes

Stop At: 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.

Duration: 15 minutes

Stop At: 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.

Duration: 15 minutes

Stop At:

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:

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

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

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

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!
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