Chicago Loop Self Guided Ghosts Gangsters and Secrets Tour

Downtown Chicago has a dark history hiding in plain sight. This self-guided audio tour takes you through the Loop on your own schedule, with narration on your phone at every stop. Start at the Chicago Riverwalk, where the SS Eastland rolled over at its dock in 1915. Walk into Death Alley behind the site of the Iroquois Theater fire. Hear the ghost stories of the Palmer House and the Congress Plaza Hotel, the secrets of the Rookery, and the stories beneath Willis Tower, then finish on the steps of the Art Institute. No group, no guide, and no fixed start time. Go at your own pace, stop for a drink along the way, and replay any story you like. All you need is a phone and headphones.

1. 1

   Chicago Riverwalk

   15 min

   Start at the memorial to the SS Eastland, which rolled over at its dock on the Chicago River in July 1915 and killed 844 people, most of them factory workers and their families heading to a company picnic. Your audio guide tells how it happened just feet from shore, and why the river has never quite let it go.

2. 2

   James M. Nederlander Theatre

   10 min

   Viewed from outside. The tour does not go in. Walk into Couch Place, the narrow alley behind the theater that stands on the site of the Iroquois Theater. During the 1903 fire there, more than 600 people died, many of them trapped behind locked exits, and the alley earned the name Death Alley.

3. 3

   Palmer House Hilton Historic Lobby

   10 min

   The Palmer House opened in 1871 and burned to the ground just 13 days later in the Great Chicago Fire. Rebuilt and still operating today, it is one of the oldest hotels in the country, and your audio guide shares the ghost stories guests and staff still tell. You can step inside to see the famous lobby ceiling.

4. 4

   The Rookery Building

   10 min

   Stand outside the Rookery, an 1888 masterpiece on LaSalle Street said to be haunted by its own brilliant architect, John Root, who died young just a few years after it opened. Your audio guide tells his story and why some believe he never left.

5. 5

   Skydeck Chicago - Willis Tower

   10 min

   Viewed from outside. The tour does not go in. Look up at Willis Tower, once the tallest building in the world. Your audio guide explores the fear of stepping onto the glass Ledge, 1,353 feet above the street, and the day the Ledge cracked under visitors' feet. Going up to the Skydeck is optional and ticketed separately.

6. 6

   Grant Park

   15 min

   Across Michigan Avenue from Grant Park stands the Congress Plaza Hotel, built in 1893 for the World's Columbian Exposition and often called one of the most haunted hotels in America. Your audio guide covers its ties to Al Capone and the apparitions guests still report.

7. 7

   The Art Institute of Chicago

   10 min

   Viewed from outside. The tour does not go in. Finish on the steps of the Art Institute, guarded by its famous bronze lions, where your audio guide closes the tour with the final secret of the Loop. Visiting the museum afterward is optional and ticketed separately.

• Wheelchair accessible
• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Public transportation options are available nearby
• Suitable for all physical fitness levels

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