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!

15 minutes • Admission Ticket Free

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.

15 minutes • Admission Ticket Not Included

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!

15 minutes • Admission Ticket Not Included

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.

15 minutes • Admission Ticket Free

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.

15 minutes • Admission Ticket Free

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

15 minutes • Admission Ticket Free